foreign [Music] the following is intended for mature audiences only discretion is advised thank you so much for downloading this episode of so what do you really do the podcast where I your host dinner Dennis Miller talks to artists and entertainers about their day jobs and on this episode of the podcast the voice does not get any better it's not even great right now oh I think this is just what my voice is going to be it's not it's not getting worse for those who have been listening for a while
if you're a first-time listener the people who have been listening for a while know what I'm talking about for those first time viewers and first-time listeners welcome to the podcast uh what I'm referring to is my voice uh as a voice artist radio personality I guess former radio personality uh actor comedian and now tour guide narrator for Boston doctors my voice is all I have and I've never lost it before I've never sounded this well I've always sounded bad but I've never sounded this weak vo
iced uh but it's it's after you know 20 to 25 tours a week or plus I did almost 30 tours the other week Memorial Day weekend um and now I'm hitting my stride this is how I sound all the time now uh there's no straining it's not getting worse but the problem is it's not getting better it's not getting back to where it's supposed to be so that's kind of the worry uh and this podcast I recorded my friend Brian Kiley uh comedian and writer writer for accounting for 27 years and right around the fina
l season for Ellen DeGeneres's daytime talk show uh he and I recorded when my voice was pretty much at its worst so apologies in advance for how I sound uh apologies for the past how I regularly sound because it sounds like a truck full of screaming babies crashing into a nitroglycerin Factory it's it's cavernous and nasally and it is my voice and it uh it's sounding worse this is actually one of those other podcasts that I always talk about where it's my pandemic friends friends who I made duri
ng the pandemic through Zoom comedy uh Brian Kiley I opened for him Flappers comedy uh every Tuesday for a month uh I hosted in for him and we had a lineup of comedians that refer together and just repetitiously I mean I became friends over the Internet We performed together in uh the North Carolina Comedy Festival back in 2021 which was fun we got to hang out have lunch and we'll talk about it but yeah it's when I was in LA we didn't get to hang out well when he comes to Boston we didn't get to
hang out but you know we we enjoy each other's company we're friends and I'm really glad he came on the show because we got to talk to a writer for a TV show for somebody who was there for a long time you know we also got to talk to somebody who was positive about the covid-19 zoom comedy world you know those are the things that you don't hear a lot a lot of people talk negatively about Zoom comedy Brian was hitting the the the shows every night Laurie kilmartin former guest of the podcast Larr
y kill Martin also very heavy into Zoom comedy so is her co-host of her podcast Jackie cation Maria Bamford Ron funches there's so many people that did it uh throwing the pandemic got on their webcams and did comedy for people but would you hear about is other people how bad it was how much I hated it my mother whatever it's good and bad like every other show you know is it like performing live for a person no what do I always say to it it's Methadone for a performer's addiction you know and I e
njoyed it I got to meet France there was something good that came out of the pandemic you know whether I've successfully followed up with all those friendships or you know I don't want to say take advantage of because that sounds like I was manipulating things but it's like did I capitalize a lot on my relationships not necessarily but the future is still yet to be written in my career in comedy so we shall see how things go anyway please enjoy my conversation with comedian and writer Brian Kile
y it's a look before you tell me all about the flight it's a good thing that you were delayed and that wasn't because I uh caught a huge cold oh okay and I would have felt terrible if I gave someone else this cold yeah no I that's why I didn't come by Saturday after the show because I was like so congested and I lost my voice from uh doing nine boss induct tours this weekend yeah how were the Duck Tours it is going to be an interesting job I'm I'm literally giving everything up with the exceptio
n of like I'm host just keeping one trivia gig and I'm still doing stand-up when I can but I've given up everything else like all my freelance work all my editing work I'm focusing everything like all my financial basket all my financial eggs are in this one doctor basket and I have to hope that it pays off uh I love the doctor we wait we want when my kids were little uh my daughter was a baby when we did it well it sounds like next time you come around you're gonna have to try and do it again I
would love it we we did it in we did it in Boston we did it in Philadelphia we did it I think in Seattle is that right it's there's lots of cities have those vehicles and weirdly it's not a chain none of the other cities are connected to each other as far as I know oh really yeah they're all independent they all kind of like even at one time here in Boston there was a second company doing Duck Tours that was not affiliated with the Boston Duck Tours crazy um we had Captain Splash Captain splash
do you have a stage name I do I am a ukulele playing punk rocker named UK Lee nice love it that's so great I picked the thing most closest to my own actual Personality yeah good for you for you uh we we love to build it though so cool yeah you know slash trucks or whatever they are you know yeah basically they're they're trucks that are boats and boats that are trucks yeah yeah so yeah sorry I mean why did your flight is there like I know I I tried to sympathize with you with your uh with your
flights from LA to Boston where I was like oh in February I had similar issues my issues were because of snow what was the why were your flights getting canceled why was it so difficult to get to Boston they had some they said some kind of mechanical who knows you know they could be full of [ __ ] but and our flight was delayed you know four hours going back so we had two nightmare flights there and back oh I'm sorry to hear that I mean and especially on top of like you're only coming in for lik
e two days so you're getting near your jet lag you're over tired and then you have to perform it's one it's a different thing it was like oh we're going for a vacation but you also have to be up and present and aware of what's going on that's true so how was the uh the Boston Comedy Festival it was good it was really good and you know my kids came which was I I wasn't sure that they were going to be able to so um that made it great it was uh they they like they enjoyed the competition you know I
kind of watched I was kind of washed with half an a year because I was kind of had to prepare for my thing and all that stuff but um yeah it was really good it was a very memorable event you know I mean especially not just you know I mean you're performing in the most prestigious one of the most prestigious comedy festivals in the country you know you're invited to but also they awarded you was it Lifetime Achievement is that what that award was it was and I actually had to give up I gave like
a little speech which you know it's not that's what I was so nervous about because it's like you know I I don't go around giving speeches so that was a whole different thing you know yeah that you can't give a one-liner speech exactly exactly yeah so I I I just kind of um I wanted to explain to them who I was you know and I just kind of documented my career and tell some anecdotes and things and and you know try to thank uh the people who've helped me out and all that stuff so yeah well you had
to talk earnestly for once in front of people you had to open up emotionally whereas usually your one-liners are very very devoid of emotion yes exactly and I actually got choked up on stage which never happens except maybe when I was bombing in traffic well I'm glad here's the the thing when it comes to lifetime achievement awards like you're you know you're you're not an old man but you're not young like your career is not over you it's like who is the award for your lifetime you're like ah yo
u still got a couple decades left under your belt hopefully well I I was worried that I'm like are they telling me it's time to go because I you know I I'm vaguely insulted by this before hey everything you did was great up until now and we've had enough of you well you've uh I'm sure did you ever compete in the BCF before you left for La back when they were doing it in the early years no I I I I never did I um the last contest I remember well I did do the Johnny Carson Festival in 2014 which I
didn't realize it was a contest until I got there and then I did the I did the designer thing in Boston years ago what I remember at that we had to we had the auditions were in the afternoon everyone had two minutes and there were 110 people or something and if you passed with your two minutes they picked eight people to go on to the finals you know to that to whatever to the finals that night and one guy came in off the street just somebody wasn't and he told this long Street joke and after two
minutes they shut your microphone off so he in fact came in and did a two-minute setup to a joke and then they were like thank you very much and never never got to the punch plan you know sometimes cutting them off before the end might actually be the most beneficial thing you can do to certain people in comedy that's true that's true well I just gotta imagine that that's going from like I can't imagine it yet because I'm not at that point in my career but like competing in a com in a competiti
on and then being awarded an award at the at a competition like that's and like I gotta imagine that's a surrealistic feeling like I just got my first invite to a festival not a submit hey pay a submission fee I just got an email uh from a festival in New Orleans is like hey we want you to be a featured person in this Festival we'll get you everything set up and taken out and I was like you you bought me you know oh my God like we're gonna give you a spot because you paid money right right right
oh yeah that's that's huge and I feel like all these little steps you take are all you know and then sometimes people are like no we still want you to pay money to come to work well with the uh with come here also it's got to be you know uh I know you've been back once I'm during the pandemic when we were hanging out on Zoom shows we had talked you know it was a while before you were able to come back home because of everything going on but this is is this your this isn't the first time you've
been back to Boston this is the pandemic right I think there was one other time you're in town yes I came in because so my daughter went to BC and she graduated in 2020 but pandemic of course so I came in I came in that March of 2020 to help her pack up and and bring stuff back and then uh her graduation the actual graduation didn't take place until uh October of um 2021 and I remember you tell me you were coming in town for the graduation almost a year and a half afterwards but so you haven't b
een back since uh 2021 then right right yeah you know which you know I I kovitz kind of messed everything up I used to come back once a year then when my daughter was here I'd try to come back twice a year you know but um you know with covet I feel like I would you know we were all just kind of stuck in our where we were you know yeah I mean I like my family's in Baltimore it's 400 miles away I live in Boston your family's in Boston you live in L.A it's entire across the country I'm okay with no
t seeing my family it doesn't bother me that like in fact I wish there was still more pandemics I'm like sorry Ma I can't come sorry don't want to get you sick you know but you like your family so I gotta understand how that was the struggle for your like I want to come see my family well I was I was I mean there's good things that came out of it uh in terms of what the pandemic being yeah there was good things that came out of the pandemic I mean I mean you wanted to see your family so that's a
bad thing but I mean you know I the amount of connections and friendships that I made through doing Zoom comedy during that that you know year and a half two year period um like when I went to LA in February I was meeting people who I made very deep connection relationships with online and then got to see them for the first time in person and they didn't feel like I was meeting somebody who it felt like I was meeting an old friend already you know right right I feel like I don't know if anyone
else came out with that kind of connection to people between like Clubhouse Zoom Google Hangouts and other these things I felt like I actually was seeing real friends I don't know how you know your experience with it it's because you are somebody who did a ton of Zoom comedy I did do a ton of Zoom shows and I did meet a bunch of comics from around the country some of whom I've still never met for in person um and one that I see like I know like my writing group now we just meet us and we're like
wait why you know it's so much easier to just do this and not have to drive an hour and drive an hour home and be able to chat all that stuff it's like nope go in the other room have your meeting for it for an hour and then you're done oh love it you know some people initially shun the whole Zoom thing um like I said you embraced it what was it about Zoom comedy for you that made you like oh I'm gonna jump on this and and use it well I know some people didn't do it at all and to me it was bette
r than nothing you know I mean one nice thing it was nice to walk in the other room do a set and then you come back and it's like all right well I I was back 10 minutes later you know um but I mean shows were difficult where I'd come off and my wife would go how was your show I would say I have no idea I don't know if you felt like it but I was I also I have a terrible habit of when I'm on stage I'll zero in on that person who's not laughing you know and with zoom I had to find the one person wh
o was laughing you know everyone's got their cameras on you know and you like wait is anyone here and then you're like oh that guy's laughing okay I'm gonna focus on him so um but I found it was better than nothing I could still write stuff during the day and try it out that night you know it was like and some some days that was about as much human contact as I had so I I looked forward to it you know yeah I I there's put sometimes where I miss doing like Clubhouse and zoom shows where I'm like
in the middle of the afternoon like oh man I wish I could just open an app and hang out with five to ten people and share our little inside jokes yes yeah at night instead of going out and and traveling somewhere I can just come down here do a show and then go right take my dog go right for our walk and go right to bed and and satiate that that need for for contact yeah and I don't I don't I don't find the person not laughing I find I'm so attuned to looking for Laughs just because I've become t
hat way because hey I worked in radio I worked in TV I'm already accustomed to like talking to nobody in a room by myself well it was also nice you know I could do a show here at 7 pm and people in Boston with friends of mine at Boston would be watching at 10 p.m you know so that happened over zoom and also what Flappers would do a club in here in Burbank they would have me book the show in effect they go okay do you want a headline and I said no let me host I'll book the show and then I could h
ave a friend of mine from New York and introduce her and then I'd have a friend of mine from Boston introduce him but then I'd have a friend from L.A so it was kind of nice to have that you know you're you're having all your comedy friends all around the country doing a show and you're kind of like hosting a party yeah I mean there was a buddy of mine put me in charge of like one Sunday a month show Even after the pandemic for KO comedy uh and I'm pretty sure you did one of the kids yeah yeah th
at was the best part is like all the people I don't get to see all the time I can book them and there was a point where I was like oh I should probably put a Boston comedian I was like but I want to hang out with my New York friends and my La friends and my Austin friends and my Chicago friends and my Boise Idaho friends like every time I thought about who to book on it I did not book anyone who I knew personally day-to-day operations I was like I could see them I want to see my other friends su
re sure I do think a funny thing over Zoom is sometimes I would finally meet the person and I've done a dozen or so Zoom shows it's like wait you're really tall I thought you were really sure or whatever you know what I mean like so sometimes they don't look the same in person we all look shorter in these little boxes yeah yeah well I honestly did that to your friend Dana Eagle uh when I came to La I was doing a show at Burbank she was in the other room I come out and I'm just sitting talking ha
nging out with her talking and it was like 45 minutes went by when she the light bulb went off she was like oh wait dinner Dennis yes we've done Zoom shows together I just thought you were just some new comedian who came to town she was like I didn't recognize you without all your equipment and your backdrops and everything behind you oh funny like I didn't even introduced I was just like hey Dana what's up and she's like hey what's up we're talking talking it's like I've been wondering this who
le time who you were driving me crazy that sounds like her [Laughter] do you think you adapted to zoom better because when you were uh writing I think was you were you when the pandemic hit you were still writing for Conan right I was yeah so you already had moved Conan's writing room moved to a zoom uh setup during the pandemic as well is that why you think you may have been adapted because you were already doing it during the day for work yeah that's true that's true and I do think I I do thin
k my style lent itself to zoom in that you can do a quick joke I think it's harder to do a long story over zoom and not be interrupted oh boy as a person who tells long stories boy do I know that right because I found my my longer jokes even had more trouble than than just a quick joke you know uh it's so easy to get interrupted over Zoom I was doing a show with my Wayne my friend Wayne Federman and halfway through his act you know who's ever yes of the podcast yes okay who's ever uh interruptin
g my uh so who's ever um who's ever the loudest on Zoom gets the mic so to speak you know so he got interrupted this old woman he's doing his set and mid punchline this old woman said saying I'm watching the comedy show I'm watching the conversation and we never heard the punchline and we were dying oh my God there was a lot of unexpected uh comical moments yes there was somebody coming in the room screaming and yelling or people's kids like Dad why are you making so much noise yes yes there's a
lot of that when when everything started during the pandemic for you as a writer uh switching over to the to the what did a writer's room on Zoom look like uh in the case of a late night TV show because I've talked to a couple other writers some of them basically did like hourly check-ins some other people kind of did like eight hours in a room together just slightly contemplating and oh my God tapping on their pens oh I just like I can't imagine that no we had one or two meetings a day also wh
at happened was you know Laura Martin and I would continue to write monologue jokes for him and he would read them you know he's doing the show with us on his phone at home um and so he would read these jokes off note cards and then after a while he um he's like doing these jokes to no one uh I don't want to do that so he stopped doing that after a while uh what they would do was if you got a sketch approved uh and you could only do you couldn't really do sketches with multiple people in it unle
ss it was like a married couple that were just like in lockdown together or something like that but I wrote a sketch where it was about a guy who he had his business was he had a package dealing business from people's porches and he was so overwhelmed that he had to he was high he was looking to hire people to join his his Sports packaging stealing business so it was just him talking to camera so it was one of the actors we use um Matt McCarthy who he just did it on his own you know we sent him
a script and he just he just did it on his at his house alone um on his own phone or whatever you know so we had to kind of work around things like that yeah I can't imagine having like I did a couple of like single person sketch ideas uh at the beginning of the pandemic to get like re-familiar with like Premiere uh editing like to jump back like I haven't used Premiere I haven't done video editing since 911. uh and so it's like oh let me learn relearn while I have this time so I had to create s
ketches and there's so it was so hard creating one man sketch there was one sketch literally that had written forever that is mostly one person and I literally had to play my other self and go nobody's gonna get this I like I didn't change enough clothes to realize that I'm looking at myself as a different person they're like why is he now in the chair foreign that Conan show was coming to an end what was your feelings I know we kind of talked about during the pandemic but yeah yeah no I you kno
w I was it's that thing um but I was also grateful you know I was here 27 years so I really can't complain too much you know you've been with him since almost the beginning right I started uh six months into the first season so um it was a long run and um you know I still enjoyed it I I if it kept going I would have kept going with them you know and then I was able to jump on the last season of Allen which was fun um but yeah which by the way at that point you get out of one show that's cancelin
g you move to another show they're canceling that it's like at what point do you feel like is it me oh definitely I I was thinking of of trying to join shows that I hate just to get them off the air that's a perfect plan I feel like everything I get a part of I somehow sabotage maybe that's what I'll start doing is joining my enemies yeah yes laughs um but yeah I I you know we had a nice long run it's it's you always want to keep going as long as you can you know well it's good that you never go
t burned out on it um because some people can you know they they want to change up they want different or they get yeah monotonous uh it's nice to hear that you did something for literally almost three decades and we're still a fan of it yes I mean I I certainly would have liked to have written for you know jumped to a sitcom or something but you know with having kids and stuff you're afraid that what if the show gets canceled then that's happened to some projects they leave to a sitcom a sitcom
get canceled and they're at our work so I I as much as I would have liked the variety I do um I do like being able to put my kids through college and all that kind of thing and you know I got to work with really funny people every day and laugh my ass off every day so I really I I loved it I can't you know I wish you know I I want more of it let's let's I want to get in another's writers bro well it's so you were a part of two amazingly you know long and well-known uh talk shows that you're wri
ting monologue jokes for both of them are are done with and over what's the plan now like it you know is is it are you trying to find another show to write on are you trying to change gears are you even thinking about going to back to touring lifestyle well it's funny I have been I have been doing a lot of stand up and I've been touring the shows are fun the the flying and the long drives and all that stuff the wear and tear is hard especially after this last weekend yeah it was I know I mean it
was a nightmare getting in and out of Boston but show you know I've been pilots and things so I'd love to sell a show or create a show um and you know if an existing show wanted to have me in the room to have punch-up jokes or whatever sounds good to me I'd love that too you know well there's enough uh you know former boss of people who've come through the Simpsons they're always uh you know like that's how uh Dana Gould got his job just being comedian and they brought him in from punch-up just
talk to enough Boston guys like somebody will get you in that room enough Harvard guys I hope so yeah yeah let's let's spread that rubber around by the way I feel like the old aunt is like you know what yes you do to do you comedy thing you should go on that Saturday Night Live why don't you just go one Saturday Night Live I know my sisters always recommending those I should write on it's like yeah I'd be happy to it's not I'm not saying no it's not like I'm the one making the decisions well do
you do you think writing do you think writing uh for a talk show prepared you would prepare you for writing and show running or do you think that's a skill that you developed before well let's you know what before you answer that question let's go back and talk about uh what got you into comedy because you do a ton of writing prior to being a comedian were you of big into writing were you a big writer growing up um I it's funny I when I was in high school I wrote sports for our I covered our hi
gh school hockey team and baseball team so I had like a little every week I had a little column uh talking about the games that week so um yeah I mean I guess I so I in effect I started getting paid to write when I was 15. um writing sports for those three years and I did want I as a kid I'd watch The Dick Van Dyke Show and I was like I'd like to be a comedy writer when I grew up so I used to write jokes and I would save them for when I needed them and um I didn't know how to go about it I didn'
t know how people got those jobs you know because you're really more comedy clubs when I was a kid but I knew of you know um so yeah I mean I I I I always I mean I would say since I was about 12 I wanted to be in comedy as a as a comedian or a comedy writer or whatever yeah that's interesting because like using dictionary diet is a great example of a very few small things like a real actual look into how a TV show gets written because that's the entire show takes place in a writer's room prior t
o that what did you have like I don't think prior to that after that the only other thing that really gave you an inside look of TV was what um uh that with uh Olivier um Lawrence Olivier did a sketch show a movie about a sketch show a show within a show um what is it it was just in my brain it just went right out of it as I was preparing to introduce it show of shows the movie show of shows yeah that was that was the only other look like behind the scenes and then then comes along 30 Rock which
is the absurdist version of a show within the show you know and then so nobody really you never really saw how the interworkers of TV go so it's interesting that you watched the Dick Van Dyke Show and was like because I remember watching reruns of the Dick Van Dyke showing like oh this is interesting look at one of them type and one of them talked that's as far as I got in my brain about it foreign that's a show that still holds up for me when I watch reruns you know well this is a terrible sto
ry I shouldn't tell the story but I actually found out because we had a joke he was on a show called diagnosis murder and CBS canceled the show so we had a joke about CBS decided to cancel the show when they realized all their viewers died four years ago yeah we kind of did it and then it was in the Entertainment Weekly and apparently Dick Van Dyke saw and he bummed out and Conan at the son of an apology letter and I'm like oh my God I'm I'm bumming on my hero here you know I mean it's one thing
to have to apologize for a joke that you wrote apologize for a joke from somebody else though you're like just sit in your rooms like do I also have to send the apology no oh and then I you know he ended up doing the show he could have been nicer I got to meet him I didn't reveal that I wrote that joke um but it was what it was it was such a treat to meet that guy after all he did for me you know well at least that's a positive story of meeting you're here as even though if you uh made them sad
yes yes you can make your hero sad sometimes so if you knew since a teenager you wanted to grow to be a comedian what was your path from childhood to becoming an actual comedian did you put anything into affected you like here at Edmondson at the 12 year old now wants to become a comedian they can literally set their life to go to Emerson college graduate with a degree in comedy and then you have to figure everything out from there that piece of paper doesn't get you a job at a comedy club but
it gets you on the path it's so true I it was I didn't know how to go about it you know I I just knew I wanted to do this thing but when I was a sophomore in college I saw I saw my first live comedy show and the headliner was Barry crimmins uh Bearcat who I thought was great and I met him after the show and we ended up meeting for coffee and I brought some jokes that he critiqued and he let me come to the dig hole for free whenever I wanted which I went all the time and then I took a summer scho
ol class at Emerson uh taught by Dennis Leary oh wow so what years what year were you in what years were you in college when was this happening uh in the early 80s okay so so basically the tail end of the the 77 late 70s early age comedy bill yeah so I started early or early 80s I was at I was at Boston College and uh taking that class then then they recommend that I keep going so I went I would go the Ding Ho and I'd go to the comic connection and I started getting little 20 gigs thirty dollar
gigs whatever fifty dollar gigs if I was lucky when I was in college and then um then I started doing it full time when I graduated what did you graduate what did you end up going to college for I was an English major okay I mean that's that's that's kind of in the path of that like that that's you know teach it teaches the discipline of writing the the it teaches you the imagery of wording yep yeah so you are already you you had a plan you had a plan you you were you're you're downplaying yours
elf like I don't know how to get there what you did is you went to the school to learn about words to be a guy that used words to make money see you you know you always sell yourself short Brian I I had a vague plan I didn't know I had a very cloudy plan that night I knew somehow I was I was determined to get there I just didn't know how really but you know I'm glad that it worked out well we look at now here in Boston at the Ding Ho which is you know like uh it's I mean bear crims has that docu
mentary about him growing up uh and his if you if you want a sad story watch Barry kerman's documentary but uh the dingho is an Institute to us here not a lot of people know about it outside of here my friend's fans follow me there made a movie called when stand up stood out that was about the time period back in Boston yeah there's that one as well so it's like did you realize that the time when you were going to the Ding Ho that it was as pivotal as as we remember it as is now like when when y
ou're in that time period going to the Jing hell we with ceremon you're like this is like this is it this is the comedy club see it was a very special place like I I you know you know I I couldn't believe that I was there part of it and that I knew those guides and and um yes there was a there was a romantic quality too I mean believe me you know there were bad shows here sometimes you know whatever but the whole thing was so exciting you know um and you know I was I was in awe of those Headline
rs there Steven Wright and you know Mike Donovan and Mike all those guys I I you know Katie Rogerson tingle and all those guys so yeah I I was so excited to uh be part of that scene what made you decide to leave Boston well I it's funny I kind of went Kicking and Screaming because even when I started at Conan you know my wife is a VP of a company so so you know we didn't want to pick up and move and also I only had 13-week contracts so it was kind of like well we don't know how long this is gonn
a go um so I they would let me ride from home one or two days a week you were still living in Boston when you started writing monologue jokes for Conan I was oh I never knew that yes and then I I probably stayed a little too long but um and then we then we'll I think I think once my wife left her job it was kind of like okay let's what are we doing here so we moved to New York and then I was in New York for a bunch of years and then um and then I came out with Conan when the show moved to LA wel
l how did you get the monologue writing joke a job while living in Boston I just assumed you were in New York that you had already moved to New York and got it well what happened was Conan uh there's a couple of Boston Comics that got hired there uh my friend Tom agne and Chuck scar and they were writing his model like and somebody got fired and at the time I was writing a lot of topical jokes for my aunt when I would just go out of clubs I would you know if I did 45 minutes I would do 25 minute
s of topical joke so then 20 minutes of you know so when I got my job actually last 25 minutes of materials right away um uh so I was in the habit of in those days getting the newspaper sitting down and writing jokes for the newspaper every day um so when they asked me to submit a packet a bunch of those jokes I've been doing in my act you know the thing with Taco Bell Jefferson you know you have to replenish you can't you know you can't be up there talking about the Eisenhower Administration or
whatever you know you've got a you've got to keep keep replenishing and keep it current but I I some of those jokes I was doing in my act and then I wrote some new ones and I sent the packet in and they um so the writer's packet for me was just it was just a monologue packet so it was a packet of about 50 jokes and they called me and said okay you start tomorrow well this is uh just to point out timing uh like to do that now is easy you put it together if you have the packet ready you have it w
ithin minutes in 1995 1996 when Conan started you literally had to either pack it into a manila envelope and mail it to them or were you faxing it to them I mean that was the height of Technology fax machines I I know and I I think I remember having to go to like the local coffee store and have them make a new faxes to NBC you know um yeah it's kind of it's kind of nothing to think about was that when you were working from from home writing for Conan is that did you have to fax the joke to him o
r was there a phone call or how did that process work yes I mean I would I would fax stuff in and then sometimes we would have I'd be on the phone with the other writers and we'll be spitballing and sometimes you know the funny thing about comedy is sometimes you say something in the room to make the room laugh and they go that's good let's put that and that that happened to me and Ellen do you do Wordle I know what it is but I don't do it now I'm not that smart so when Myrtle started I I was we
're at Ellen and Myrtle started and I said writing for that's going to be the easiest job in the world you know you show up at noon how much dwell dwell is good okay I'll see you guys tomorrow um and I was just kidding around the room and they go that's good and then they put it she did that in the monologue the next day I was like okay I was just I wasn't even I didn't realize I was working I just thought I was [Laughter] to make the room laugh and then go and then put it on and I'm like I was
just kidding I was you know I didn't think that was appropriate for the show or whatever so that that stuff happens all the time is there one that never worked out where like everyone in the room laughed at it and then when it went at the air it just went down the drain in the audience is there one that you can remember I remember sunset time it was just a bad Crowder the jokes were bad or the combination of both whatever but the monologue did not go well so the next day Connor comes in my offic
e he's like how do you feel when you send me out there with that you know and what I told him was if you've ever seen the you know the Hitchcock movie Rear Window very well very much yes yeah so there's a scene where you know Jimmy Stewart's got two broken legs and he thinks his neighbor Raymond Burr has murdered his wife so he sends his girlfriend Grace Kelly in to investigate when Raymond burriss off the apartment and Raymond Burke comes home early and catches her and starts manhandling I said
I feel like Jimmy Stewart watching this going oh no and he's Grace Kelly in the audience his favorite murder I I mean I gotta imagine purchasing a fax machine was like I'm buying this thing for work was a big huge kind of deal like I I'm like I have a studio here I built this studio out of spare parts that I stole from my job and radio then when I can actually afford like when I was doing it enough and I could afford to buy an actual microphone that wasn't stolen I was like that like when I lef
t radio went became a freelance podcast person I was like this is my job area this is like I have a room to do my work in is in the 90s was that the same feeling was like gotta go to Staples and buy a fax machine with all these bills with all these checks from Conan yes and I do remember when my son was a year old sometimes we'd get a you know the phone would ring and we'd go answer the phone but if we got a fax you just kind of let the facts come in and you wouldn't go the other room and he wou
ld come he would be standing there like blah blah blah you know not not speaking yet but like the thing is driven like why aren't you going to get it he was always bewildered as a baby of like I remember because uh working radio doing more than radio we were getting prep service by fax so every morning right at like 4 a.m fax machine would go off and you would get a stack of paperwork this big coming from prep services and you just take them sort through and then you'd sort through and every onc
e in a while you'd find like or in the middle of like 2 A.M or 3 P.M you would get a fax for no reason you'd pull out and it's spam it's like a sale ad that they just faxed to you were you getting spam faxes like I got a fax at work one day it's like make your penis bigger I'm like I'm gonna throw this away yeah when I would get notes that said that they were just for my wife they weren't spam they were just saying you know make your penis bigger you know all right so you eventually moved to New
York and then eventually to La that's I rap you said you say kicking and screaming there was a conversation you know that you and your wife had to have like do we continue to do this do we follow through on this how did that conversation between you and your wife go well you know once once her job ended and then it was kind of like you know you know we certainly and I you know when I had a good job and we did you know you had to um you know we wanted to keep to keep working and and and and um y
ou know then we had kids to take care of and and all that kind of stuff so yeah I think um we did think you know when I started Conan I the show was a little bit shaky in the beginning and yeah I mean it's it's that's got to be a nerve-wracking feeling where you're doing a thing and then you're seeing every day in the public eye where they're like it's not working out for this big old tall redhead guy you're like uh if it don't work out for him it doesn't work out for me yep yeah I mean I guess
there's always that that thing like there's so many jobs right here but I guess when it comes to like crew work like I've done crew stuff sound guy right obviously I'm gonna do crew work uh on on small Productions and stuff like that I feel like the feeling amongst crew is there's always another job out there but when you're a performer when you're in the the performance side of it when you're on the entertainment side when you're directly related to like writing directing starring being in thos
e things I guess there's I always thought that because there's they're not meritocus meritocracy when when you're a performer it's not based on your Merit it's based on do you fit this role yes there's so many factors and certainly it helps but you know and I know people who they weigh their whole life to get at their own sitcom and they get their sitcom and then it's canceled after one or two episodes and they're devastated you know so oh I didn't know you were friends with John Mulaney well he
said one of them you know it's so it's so bad yeah I mean or even getting a writing job in a sitcom which you've finally made it and then the show gets canceled after a couple episodes and you're back out in the street so I I was certainly very lucky to be on such a long morning show it shows that you know it shows your talent that you're a part of it for that long that you're able to uh prove that you're able because you went from one amazingly popular show to another amazingly popular show I
mean is there other outside of Oprah is there a bigger talk show than than Ellen at the time you know I said Oprah packet and [Laughter] you know that whole you know and you get a car and you get a car I get something very similar um [Laughter] [Music] you get a fax machine and you get a fax machine um what's up well you you and uh you've already written a pilot that's gone around uh the festival Circle right didn't you and Mary Gallagher put a do a pilot together my therapist we did it was a be
my therapist so we we shot five episodes of the web series um and it got us into Montreal and we got uh meetings from it and and that kind of thing and so what happens to these things you know there are people that I've met from Mad who um they ended up passing on that idea but they want you know every time I have a new thing they're happy to take a look so that kind of building those relationships you hope that uh something that ultimately comes from it you know and it was very fun to be in Mo
ntreal and to to you know put our web series you know in front of a crowd and that kind of thing was it what was it easy working alongside just somebody else writing story and structure and stuff like that I'm sure monologue jokes is just pitch joke pitch joke pitch joke it's a room full of people joking around I'm sure that's an easy concept that's an easy room to be in but when it's you and one of the person sitting around like here's this character here's their Arc here's the story this is ho
w did you and Mary get along was there a little bit of friction between the two of you while working absolutely and also she's such a she's such a terrific actress so shooting with her I kind of left her it's like I just tried not to get in the way you know um and her you know uh yes writing together was great and and um you know I I do think you have to have the right cardistry to someone then luckily we had that and uh would make each other laugh and and we felt like we um we had similar sensi
bilities which house you know because there are people that I think are funny but their sensibilities are too different for me or something you know um so yeah that was a that was a a dream gig you know I've I found I don't work well with others like I could do a collaborate I can do like a group collaboration like where we're talking about like joke structure in like a writing room but the few times I've tried to get them get together with people and work on like let's write a script together a
nd I'm like I'm okay without doing this with it without you let's take our let's let's write separately and then we'll we'll have our own projects well there is I mean it depends on the person uh you know there are people who um they always say they're gonna get together and then they never do or you know this is people that um you know you need someone with a good work ethic you also need somebody who you know you don't work with that person that they only like their ideas you know what I mean
so you want to be with that person where um that you like each other ideas and there's not that sort of ego of it's got to be my thing or whatever that you that you can um you know that you can agree on and and um and work together it's not that's and that's true take it's not an easy relationship you know but when it works you're I'm so appreciative you know you think you became a better collaborator because you had to work in a room with people so much or do you think you just naturally that w
ay yes no I think that definitely helped and one thing I had to learn at Conan was you couldn't hold on to the jokes that you loved that if if you loved a joke and they couldn't do it for whatever reason you just had to let it go you end I think with your with your act the jokes are so near to your heart but writing for a TV show or whatever uh you know they they use that expression you have to Kill Your Darlings and when you're writing scripts sometimes you have to take out a line that you love
it doesn't quite fit or whatever the reason is so it's it's really doesn't help the story move the story forward or whatever so um uh what working at Conan we were generating so much stuff and and not everything could make it to air and some things that you love didn't make it to air so you had to kind of learn to let go and not you know um not hold on too tight to those things you know what's the what's one joke that you kept trying to give them that you had to kill and nobody would ever accep
t what's the one that you're like I always wish this joke would have gotten through there was well there was a Snapchat here you know how there was always like the office was originally a British show and you know Sanford and Son was originally a British show and All in the Family was originally so I picked this idea that Conan was originally a British stone and so basically so and Cody love the idea the idea of he was gonna play the British version of him doing Conan um and with a British accen
t and just you know all the silliness that we were going to add to the show and it kept getting put off and then we just kind of ran out of time and we never got to do it and that was one that made me sad that especially since I knew probably loved the idea and I think he would have been really funny doing a British version of himself you know there was also like wasn't there a Bob Odenkirk sketch where he likes the predecessor took Coda or he did a version of Conan with Bob Odenkirk uh maybe th
e the amount of stuff I could it you know Andy talked about this too when they would show they would show like a a like a retrospective and they would show things and Annie would say you know I remember about a third of those things you know there there are so many things where you know he's in a costume he's whatever no recollection of that bit at all because there were just so many things um and people would say things to me about monologue jokes that I wrote and things I'm like I don't rememb
er that and then I look it up and go sure enough you know I went to Dr Katz that I did recently and there were jokes coming out of my mouth that I had never heard before well that's what I loved about Dr Katz growing up as a kid is I get to see my favorite comedians do jokes and then see visual reputations of it you know scream about the the fire the barbecue I know how to handle the fires absolutely and that was fun like I never it never occurred to me to picture myself as a cartoon so they get
and well I got that cartoon cell and and it was framed in our den and my little my son was nine months old and every day he would point at that picture and laugh and I don't know what there's something inherently funny about cartoons I guess but his little nine-year-old baby brain would look at it and just crack up I don't know if he knew that it was me I I it was so fascinating to me when running for a network TV show I mean things are different now like you can get away with so much on so man
y other networks you know and and you're pretty much a clean comedian so I don't think you ever had problems with standards and practices but was there ever somebody on the show that can that you worked with who consistently just kept getting shut down because like too dirty too bad can't do it too dark is there anyone that had problems with standards and practices oh yes yes so well that was for me the hard when I shifted to LMS so as we're doing 27 years on late night to go to a date time I pi
tched things in the Ellen writer's room and they'd go we can't do that and I was like what that's this um and there was this one thing there was a story about there was some beach in Spain that they were saying was being ruined because so many people going to this beach to have sex that it was ruining the beach for this stream with condoms it's you know all this stuff so I pitched this idea of a reporter reporting from that beach and you just hear the loud sounds of sex just wafting into the int
o frame and they were like yeah we can like I had the same problem with Boston duck door is like I'm just naturally subversive so I shy away from like the jokes that everyone else in my group is doing all the other tour guys are doing I'm trying to find creative original jokes that are also in my very dark tone and yeah shut down by the trainers or like no Dennis you cannot please stop referring to Paul Revere as the Elon Musk of the Revolution or that's so funny please don't call The Departed s
tarring Leonardo Dicaprio and locally known racist Mark Wahlberg stop saying those things foreign like I have a whole boss like I've written almost an entire at least a 45 minute tour of Boston that is a roast of Boston history tour that should be its own tour it's like what you know the yeah there should be a like a midnight dark tour that people know what they're in for like all the people who roll their eyes when you hear somebody mention Tom Brady that tour is for you the roast of Boston is
for you like I talked about there's a Robert Gronkowski donated 1.2 million dollars to build a playground and my joke for it was hey you can learn the jump you can learn to climb you can learn to be just like Robert Gronkowski and abandon Boston just like he did and like no no no no I better stop to that nope do not abandon us right now what is uh like with the strike going on uh I mean I don't know if you're Tech I think what's your opinion on the strike obviously everyone is for the side of mo
re money but did I did we schedule a time today that took it away from your time pick of the picket line I'm sorry I didn't mean to not help you represent yes I went yesterday and I'm trying to say okay you want me tomorrow at 11 and I'm like I have to do a podcast um I can't join you so uh yes you're uh you got me you lured me away from the picket line um and today actually it would be a good day because it's overcast it's you know it's gonna be 95 degrees here soon it's going to be a bummer oh
yeah it is but so what's what's the front lines of of the strike looking like from somebody who literally your livelihood comes from writing yes yes and you know I've been through this before we did it you know in 2007 in the beginning of 2008 we were out of work for three and a half months so um and that was you know we were in New York it was freezing you know uh December and January as you can imagine um you know I'm not I'm not on a show at the moment so that is good in that sense the probl
em is the things that I'm writing and you know I can't pitch a show now you know until the strike ends so um you know there's no um there's nothing you know for the first foreseeable future that I can do television-wise I you know I could go out and do stand up and that's what I'm doing but um yeah it's the two stars seem very far apart and um it's also the kind of thing of you know you you like to think that you're in control of your life but when you get a television you realize there are much
bigger forces at work that you're just you know uh you're not in charge of your life you know so um I I hope it gets resolved soon I'm not I'm not optimistic though this could be a long one well I think the worst thing that came out of the 2007 strike was reality TV say what you want about it I mean most of it to me is garbage you know and it's it's not even reality it's manufactured reality yes and it's funny because my daughter loves it and I I can't be a nurse she's watching Vanderpump Rules
as something and I'm like I can't be in the room for this it just makes me nauseous but I know some people love it but yeah I think I there's so many good well-written scripted shows that's what I love you know I love watching succession and and Barry and uh Better Call Saul or whatever there's so many good things oh God yes it's unfair how much talent Bill Hader has it's unfair share it with everyone else Billy hater I know but then you have these shows where you have these two people screamin
g at each other over whatever it's like oh and that's what I worry about with this strike is is we're gonna get more of that like like the the the problem is people don't care how the shows are made or what goes into them they just want to watch them well that I mean the idea of of your of robots or whatever writing your writing dialogue writing [ __ ] song You Know writing music writing uh you know everything is terrifying you know the late 90s early 2000s reminded me of when people were scream
ing for digital music the music industry didn't give it to them so what did they do they went to Napster they went to LimeWire if you had made if the music industry had made music digitally accessible to people it would have never pirated it you know and similar in this way where people want the shows and they want the content if you just give them a show they're gonna watch it hopefully we can give them something good and we can put people to work and create a good product but people can just w
atch things regardless probably likely and then what what what's going to come of it you know the people who want quality you know then that's what they're gonna they're gonna put out like I think this is disappointing I would hope Disney would have been the company that was going to be the ones that with all of the content they have they're usually from what I can always tell is pretty good about acquiring a thing and then letting people make that thing and not being too much involved with it t
hey just hire Kevin feige go make movies they hired John Favre go make Star Wars TV shows Dave filoni go make Star Wars TV shows they don't interfere they just let those guys make good quality things but they came out with a whole ABC lineup that is just reruns and reality shows and game shows and it's like Disney you could have been the one that put an end to this you can like hey let's let's I was hoping they would be the ones that build the bridge because a lot of this is really because of th
e streamers it's the streamers who have been getting away as far as I know please you're involved with all this more than I am but it seems like the streamers are the ones who have all this control and power right now and they're high on their own petards uh or their own hubris where they're like hey we don't want to pay Riders like I've heard so many people talk about going from Network to stream air streamer and back and forth and it's like networks are we're paying and then streamers weren't
and then now networks are finding out oh streamers are underpaying now we're going to underpay and it's like this technology should be a betterment for all of mankind when it comes to entertainment and it just seems like their greed is getting in the way and you know being a television writer is a great job I think people don't realize how long your hours are and you know it's it's um if you're if you're on a network show you can't work in a digital car you know and because you're just in the wr
iter's room all the time you know so um I I think they're really being ridiculous where they're they're making a ton of money they're you know especially if you've got uh you know it's so hard to get one of those jobs and to just um people shouldn't be making you know any with any job people shouldn't be making less than they were 20 years ago great Point Adam Conifer was saying and what or was it animal kind of or one of the writers was saying I heard in another podcast talking about a 20-year
experienced writers making the same amount of money as somebody who's doing writing for their very first year and there's a huge disparaging between that and that's on that's in all rights and rights is unjust yes yeah absolutely and you can take anybody you go to whatever that job they have say well how about if you were making what you were making 20 years ago people noticed you know with inflation at all 20 years of experience and all that stuff I don't think any industry is does that you kno
w I mean my very first job was at Camden Yards at Oriole Oriole Park at Camden Yards wow selling ice Italian ice iced tea and lemonade I left that job to work at an Italian pastry shop as a busboy making three dollars an hour I would leave that job and go to Home Depot pushing shopping carts for seven dollars an hour and I was like I'm making two and a half almost two and a half times more money I thought it was a huge idea and then I turned to someone else like seven dollars an hour this is gre
at they're like I make twelve seven is garbage I'm like wait what there's make more than seven dollars an hour I didn't know that and if I was making six dollars an hour now I would go insane like I'm making like the hourly I make it boss and Duck Tours is what I was making 10 years ago 12 years ago yeah the only reason I've taken that job is because it's it's for the tips yeah you know so I'm I'm going backwards financing my career for the hopes of more financial gain which is should be the pro
gression of anyone in an industry working at a job is like you start out low and as you go on your pay should increase because your experience and you're you're you're worth your value has become more of more valuable to the company right right and and if you're not good at your job you're going to be weeding out because there's so much competition so I I don't see why you know those people should be rewarded you know yeah especially when like I listened to a lot of podcasts about writers I list
en to a lot of writing for someone who does zero writing but I listen to uh writers talk about how they have to plan what shows they're going to be on so they have an income because you know you get in a writer's room and you work from you know January to April on One show and then they go to they they go to filming and now you're no longer writing so now from May to August you have to pick up another show that's supposed to Premiere in the fall or start working the fall so then you have to writ
e for that show and then you have to write a wintertime show and it's like you have to pick up two or three shows every year in a cycle to try and like continuously have an income and there's no reassurance that you're going to have that right well I think people don't realize is it's very difficult to jump from one show to the next you know if Joanne's most shows you know you don't have it in with the next show to get in or or you know they're it's very hard to it's very hard to get one job nev
er mind multiple jobs you know yeah especially since like that's if you're a freelancer that's one thing you're always hustling for work when you're writing on a show you're not technically freelance you're an employee it's just your job only lasts for a few months now with Conan you're or talk shows you know your late night shows and talk shows they go out throughout the entire year their seasons are continual you know you get a couple breaks here and there like you know John Oliver takes off f
or you know three months out of the year a month in the summer month in the winter and a month here so his writers are constantly working throughout the year for the most part of having small little sabbaticals but for most writers on like scripted shows that's not the scenario that works for them it's yeah you work for a couple months to ride a season and then bang you're out if you're even lucky to be writing that some of it I even hear the horror stories of they hire you just to write an epis
ode and thank you you we we broke all the story you write this script and you're out yep oh there's a lot of that yeah it's yes absolutely so well yeah I hope it gets me from solved soon you know all right well I appreciate you taking your time and going through it sorry we can meet face to face between the uh airplane issues and my honestly if you would have saw me Saturday it was it was it was so bad my voice was so bad this is literally the Improvement and I gotta go start doing tours again t
omorrow it's gonna be a rough week I'm glad you took the time and I do hope that the strike ends and that you get back to pitching and did you find the show uh you know you get to run the show that you've been wanting to do this whole time oh that would be a dream I'll tell you yeah get that room restarted but that's happening and hopefully I'll be back I'll be down in La this winter when everything's back to normal and we can do a flapper show together or get lunch together that would be great
I would love that lunch this time won't be uh it won't be uh Wendy's fast food drive through like it was in North Carolina that's right I'm just in the car eating that's right just shoveling Square burgers in our face like we gotta get back to the show they told us to be food at the gig and I sure think oh there's no food there was food it just ran out before you got there okay there was food I had some of it [Laughter] oh Brian uh have fun under your strike tomorrow oh uh what are you gonna wri
te on your uh your picket sign tomorrow when you go back to the picket line there are people that bring their own signs I always just get there and pick up one I I am yesterday so it's like hey that's my sign wga East Instagram uh worthiness yes yes so I have to be careful of what what signs up awesome all right well this is great talking to you I'm glad we we got to call it up on your full back story thanks it was it was a lot of fun I'm sorry I have so much free time hopefully next time I'll b
e busy on the show [Applause] [Music] the top [Music]
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