#194 Comedian Josh Gondelman is a People Pleaser

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Jeff Dwoskin 0:30

All right, Carmen, thank you so much for that amazing introduction. You get the show going each and every week, and this week was no exception. Welcome, everybody to Episode 194 of classic conversations. As always, I'm your host, Jeff Dwoskin. Great to have you back for another classic conversation. Today I'm diving deep with writer and comedian Josh Gondelman hailing from Boston living in New York, previously a head writer and executive producer for desus and mero. spent five years writing it Last Week Tonight with John Oliver four Emmys, multiple albums, etc, etc. I was with Josh had the laughing skull competition when he won back in 2010. We reflect on that and how his career just exploded after winning that Comedy Festival. Amazing Stories lie ahead with Josh Handelman. And that's coming up in just a few seconds. And in these fields. eigenes I want to remind everyone have my amazing day out of this world conversation with Angela Cartwright. That's right, Penny from Lost in space Brigitta from sound and music. Ah, such a great conversation. Check that out. Also the bonus episode of crossing the streams on our YouTube channel over 100 episodes of crossing the streams TV binge watching suggestions awaits you. But that is for another time right now. My conversation with comedian Josh God Dolman enjoy. Alright, ladies and gentlemen, I'm so excited to introduce you to my next guest. He's a touring comedian. He spent many many years at last week with John Oliver. He's won four Emmy Awards, a million other things not going to go through it all so we can actually talk about something. Ladies and gentlemen, Josh Gondelmann. Okay show.

Josh Gondelman 2:18

So good to see you. Thank you for having me.

Jeff Dwoskin 2:20

So good to see you. Again. It's been a while Josh and I met in 2010. In Atlanta, Georgia. We were both at the very first laughing skull comedy competition. There were two main differences. One, I went up and you never heard from me again, Josh won, and is now done all those things I just listed in a million other things.

Josh Gondelman 2:45

It was, it was great. There were so many people there that I either met there or like became better friends with their like, had met before, or really hung out with that weekend better. Like, it was just such a great time people that I like really, you know, consider good friends now and have followed their careers and stuff. And it was like a very exciting experience and a lot of fun.

Jeff Dwoskin 3:04

I remember hanging out with you my mistake that I made. I brought my wife and I don't mean it was a mistake to bring my wife. But this was laughing skull for me. I way over prepared for like the three minute thing that I was supposed to do. And you know, I just went through it over and over and over again to the point where it was just like if there was no looseness left to me at all. And I'm about to go on. I'm looking at the brochure. Everyone's been on Comedy Central or HBO. And here's me. I've been nowhere, except here. And then my friend texts me. I was on the show with Tom Simmons. And he texts me he goes is Tom Simmons there. That's my parents favorite comedian. He's the best. I'm like, thank you. I'm about to go off again. It's funny. I get out there you only have it was like three minutes, maybe set I get out there. I've run through my set 450,000 times. And I say a line that I've said and you know doing comedy do these jokes over and over again. A joke I've done a million times I say the line wrong. Oh, no. Worse. It gets a laugh. But I know the part that comes after it now doesn't make sense.

Josh Gondelman 4:11

Oh, shoot. Oh, that's so rough. I feel like that have been so much. I think because like when you feel like locked into something because I do that too. Or it's like if I were just going on or on a regular night, it would also it wouldn't matter, right? Like on a regular set. If you're just doing a spot at a comedy club or an opening set or even a headlining set and you say a line wrong and the next part doesn't make sense. You can either jump ship on it or you can talk through it you can say with the audience who I fuck that up. I said it wrong. I but here's like what it is and like it's a live moment. But when you're in a competition like that, or an audition or something which is so unnatural as a venue for performance, then it's like it feels so high stakes, whereas any other night if that same thing happened, you're just like, Oh, who cares? I'll never think about it again.

Jeff Dwoskin 4:54

Right? Exactly. Because I remember thinking in my head, I can't recover. It's over. It's done.

Josh Gondelman 5:00

Right, because you're performing for like a specific result. And it's so stressful because I've always felt like auditions and competent comedy competitions and stuff when you are performing with like I have, I'm playing to win. It's so hard because like, even a good set feels bad and a bad set feels worse,

Jeff Dwoskin 5:19

right? And I was I was so intimidated by everyone around me. Like I kept thinking myself, how did I get here? Everyone? Everyone seemed to know someone or be you know, and like, and I wasn't, I wasn't even in the we got we need five more people category.

Josh Gondelman 5:32

What do you think? What's the really like your tape? Like? I think that's like there's a there's something real about that. Right? It's like when you submit to something and you get in knowing no one you're like, oh, they must really want me there. They're not doing a favor for someone's manager or like, I think that's exciting,

Jeff Dwoskin 5:46

in a way. Yeah. But when you're there, it seems like everyone's you know, rubbing elbows and stuff. Oh, man, I think I kind of felt like, you know, like, there's always that one table at a wedding or bar mitzvah. There's just the leftover view. Right? at that table,

Josh Gondelman 6:00

you You're like the only person from someone's old job that's at this event, and then you're talking to like their family podiatrist or something.

Jeff Dwoskin 6:09

Right? I remember hanging out with you and you were crushing. And I remember loving your comedy so much. And my wife, I said, I'm talking to Josh condom and she goes, you're talking to Josh like she remembered you too. Oh, that's so nice. It was a fun weekend. Overall, I remember we were we hung out at the Clermont Lounge, which is crazy. I don't even know how to explain it to people. It's like we're strip clubs. It's a strip club in Atlanta, Georgia. Yeah, but it's like the D level strippers and but that's what it's supposed to be.

Josh Gondelman 6:38

I think there's this kind of there's this. It's like a like, indie strip club, if that makes sense. Like, I feel like most strip clubs and I don't know that much about the industry, but like, it feels like most of them are technically independent, right? Like they're owned. They're not part of like big national strip club chains. But this one has, it was like almost like a punk rock strip club where the dancers had like less of a kind of mainstream strip club aesthetic. And also, it just like was kind of a grimy place like in terms of like, oh, yeah, people can still smoke in bars in certain places in the south, which I totally lost sight of living in the northeast and like so there was just that that level of like, oh, people are just like ripping butts and drinking cheap beers. And, and I don't even remember like a dancer performing the whole time that we were there. I just remember like the strippers being like, around.

Jeff Dwoskin 7:29

I remember one was so many tattoos on her. That was ridiculous. And another woman

Josh Gondelman 7:35

which I think is kind of non traditional. I'm not like a big strip club guy. But I think like there are people who have trouble finding work, or you know, because like the tattoos are like not industry standard or have not been in the past.

Jeff Dwoskin 7:47

Right. And then there was another woman who I remember crush pans under Yes.

Josh Gondelman 7:52

It was gold. The she's like famous. She's like locally famous, or that the one thing that this like is a rumor that someone told me and I don't know if it's true, but it's that the bartender there was this one bartender who worked there for a while and was like, I want to give stripping a shot and tried and there was kind of like a mild revolt among customers because she was too like conventionally attractive. And people like this isn't why we come here. We don't come here for the experience that you get at like our regular club, but it is it's like an Atlanta institution. And I was still I didn't know what I was supposed to get from it. You know what I mean? Except for the experience of like, Oh, I've never been to a place quite like this before.

Jeff Dwoskin 8:32

No, and just for anyone listening because it's hard to imagine, but if you were to say, Oh, I was at the Clermont lounge and two people died. I think the the normal Atlanta Georgia reaction would be only two

Josh Gondelman 8:42

Yeah, it felt like the vibe was like the bar that Patrick Swayze worked at in Roadhouse like it had that kind of energy like like a saw dusty energy and again, this is not to speak ill of the people who work there at all it just like that is the vibe that they're going for. It's like a little dingy I think oh

Jeff Dwoskin 9:02

yeah, don't mistake this last five minutes. This is a high recommendation to go to

Josh Gondelman 9:07

totally it's like a real it's a local it is a local legend. Like I feel like every time I've been to Atlanta, you go oh, I've got a couple that are like the show ends at 10 or whatever and I use their place to get food around here and then every time zone goes okay but you've been to the Claremont Right? Like you're not going to leave town never haven't gotten there. Like it's one of those things though. I feel like people who live there love to recommend to tourists and visitors.

Jeff Dwoskin 9:29

Right? Like if you looked it up and there was like a three Yelp review average that'd be high house.

Josh Gondelman 9:35

It's also Atlanta is such a legendary strip club city that it feels like it makes sense that there is this kind of strip club counterculture. You know what I mean? Like there's so like, there are so many it's like one of the places you hear about being like the most and biggest strip clubs in, in America. So I get why there would be like, Oh, here's the alt version of that because it's such a big industry.

Jeff Dwoskin 9:56

So alt right, so everyone's everyone Google that and check that out. Going backwards in time just for a moment. Yeah. Before laughing skull. You hail from Boston. Yeah. What was it? Where were you comedy wise before laughing skull.

Josh Gondelman 10:08

So I was still living in Boston. I'm in New York. Now. I've been here for basically 10 years. And I was in Boston, I had done a couple of festivals. I've done the Boston Comedy Festival a couple of times, I think. And that was, that was like an exciting step for because that's also a contest. And I was I had done that. And I think probably at that point, I'd like gotten to the semifinals. And so he's starting to feel like okay, I'm progressing. I had started to work at a bunch more of the clubs I was probably, I guess, is 2010. I was like, kind of ensconced mostly as like a middle act right like the the kind of the prison that goes on before the headliner. After the MC in Massachusetts, I was working pretty regularly on the weekends. But I had hit a point where this festival became like a real turning point for me. And it wasn't just what the festival did like it because I did get to go on the road a lot more afterwards, I got a college agent from the festival. And so I started doing a couple of college gigs a year, but it less that, like it changed my life, materially. And then I was like, on the road full time, which I was not, but it changed the way I perceived of what was possible for my career. And it made me think like, Okay, I think I've achieved everything I'm going to in Massachusetts, and I was at the time at the time, the laughing skull festival, I was 25. And I'd been doing comedy for about six years. And so I was doing pretty well. But I was still a long way from kind of cracking into this class of you England headliner, which are like there's so many legendary comics that still are working regularly around New England, and I could see how far away I was from like, being business wise, like, you know, cracking into those booking rotations in the same way of like, oh, you're a headliner, and honestly, my comedy was not there. Like these are guys that had been there were like, 20 year standup veterans by the time I started, and so there's just no way especially because I was like a young, kind of, like dorky guy. And I just didn't have the like, the stage presence and the the like, feel for the craft, that people who've been doing it for as long as I had some, I had a few good jokes, but I wasn't like, I didn't have like headliner poise at all, especially going into a rough room and going like, Okay, I'm going to headline this youth hockey benefit at an Elks Lodge. And I'm just like, people are gonna want to see me and I'm going to command the room. And I was just so far off from that, even if you know, I and I didn't have that like rock solid hour, either that you need for those kinds of gigs, but I just didn't have the chops either. So I was like, I was an emerging comic in the New England scene kind of thriving, but like, saw a pretty low ceiling for my development over the next few years, and was starting to feel a little bit like, Okay, what am I really doing?

Jeff Dwoskin 12:47

So I'm gonna go and take a quick break. But I do want to thank you all for your support of the sponsors. When you support the sponsors. You're supporting us here at Classic conversations. And that's how we keep the lights on. And now back to my conversation with Josh condiment, we're heading back to laughing skull to go deeper into his path to victory. And we're back so as I remember laughing skull is that there were definitely people that were favored to win. And, and I remember after I completely imploded, you became I remember my wife and I, we you became the one we were watching. We became team Josh, I plan I remember like, just being there just you listen to things and it was just some guy with all these credits, and he was supposed to win. You know what I mean? There's always a comic that way. Yeah, that guy's and but you just kept knocking it out of the park, almost like like, just silently just crashing everywhere. And I remember it the final thing, this guy who probably started believing his own press, right, he didn't deliver and you just blew the roof.

Josh Gondelman 13:44

I had a really fun set. I remember that last one, especially. And I remember feeling really good coming off stage, especially because some of the judges were people of like influence in other parts of the industry. So I was just like, these people that I've been trying to get in front of for years and hoping to impress have just seen me have a really strong as as strong as I was capable of having for sure. Like, I had maxed out on my capability that night, you know, whatever, however good anyone can be. I did the best I could. And the audience responded like that. And I felt like, okay, great. They saw me under the ideal circumstances. And now if I'm not the guy they want, it's not because they haven't seen me deliver. It's just because they don't like me. And so it went really, really great. And it led to I believe that summer I had kind of been on the fence to do the great American festival. I was like on the bubble for getting a spot of the great American festival and gosh, what's the name of the town? It's Johnny Carson's hometown in Nebraska, Norfolk, Nebraska. And I ended up getting to like, basically that pushed me over the edge for that and I met a bunch of great people there just kind of like set things in motion little by little going from being like completely unknown, except for from comics that I'd worked with. Like I think I had lots of comedy friends who had come through Boston or I'd seen when I was visiting New York or whatever, but this was the kind of thing that like I worked with a bunch of comics out of town and Just like it like expanded my world, little by little, and I was really I felt really good about that said, I'm sure if I watched it now I would be like, I can't believe I ever did those jokes. But like for six years, then I feel like oh yeah, I really I really did

Jeff Dwoskin 15:12

it. No, it was amazing. And I don't tell the story about the other guy. I only mentioned that because it's like, you always have to believe in yourself or ignore everything. That's the outside forces that are you know, jibber jabbering and all that kind of stuff. And frankly, I never thought the other guy was that great. You know, I didn't I don't even know who he is. I don't even remember. I don't remember ever. I didn't even know him then. Anyway. So it was it was amazing, kind of Thank you seeing you win. And then I remember after you won, you stopped talking to everybody off cut. It was

Josh Gondelman 15:40

$500 I think that's what it was, I think this is their five plus all this work on the road that like some came through, some didn't. But you know, they kind of were like, hey, these clubs will book you. And then I had to chase that down on my own. And some of it was great. Like, oh, man, wow, what a fun weekend at this club. And there were places that I just couldn't sell enough tickets to headline and was like, relatively inexperienced, but like a few places that I came in as a feature and just had great experiences and worked with people that I really liked and admired. And that was a blast and then other places where I was like, this is a learning experience and I'm glad I did it but like wow, this is you know, there's a lyric by in a song by the hold steady, that's about I mean, the song is like kind of about film as a metaphor for like, are in the textbook. They have a lot of songs kind of about that touch on like the experience of being in a band and the Lyric is some nights it's just entertainment and some other nights it's work and like that. I really felt that at some of those nights were like, you know, there's that night where it's like, oh, it's a competition and people from the entertainment industry are here and tons of comedians from around the country are hanging out and like this is like showbiz where they were in entertainment and then there's the nights where I'm like just getting you know headlining before I'm ready especially for certain rooms getting buried by my feature in in Chattanooga, Tennessee, and then eventually like club owner who hated me flip flopping me with the feature who was like very funny and it also been I believe, at the laughing scholar here, which is where I met him this dude Landry who just crushes

Jeff Dwoskin 17:05

it's fun. It has it's I've heard stories of that. I remember there was an old story at a local club where Jon Stewart had to move from the headliner to the feature I'm going back decades.

Josh Gondelman 17:13

Oh, I mean, like Yeah 2019

Jeff Dwoskin 17:16

Yeah 2019

Josh Gondelman 17:18

via via feature who's like huge on tick tock. And I tried to be like really honest about that, because I do feel really fortunate in my career. And I think I'm like a pretty good comedian. But I think that there's like when you see the kind of narratives of people's success or whatever, I just don't want to be one of those people that like leaves out the like bummer parts where you're just like, Yeah, I just like this happened and I was off and running my life was amazing after that,

Jeff Dwoskin 17:45

the only good stories are the ones where you completely fail. Those are the ones when I get together with my comedy friends. Those are the ones we tell nobody's interested in the perfect golden show. No

Josh Gondelman 17:55

even like the moments that like went unexpectedly well on stage I think like you really just want to hear the disasters or the times that things went well and then you know, I think like, Hey, I had a great set and the only time that a story is good that starts that way is like then if some something bad happens to you immediately following I had a great set of in the club owner fired me because I mentioned I have a joke about rhinoceroses and his father was trampled by a rhinoceros and he was just like, I can't hear that you know what I mean? Like that kind of stuff is so funny to me but like yeah, just like yeah, best weekend of my life crushed it felt amazing you know that the My Living Skills story is like a boring story from my perspective, like to tell because it just was really exciting. But it is like kind of a foundational like, it was like the first thing in my career that was like a real credit in my bio that like traveled and wasn't just like, oh, you know, like semi finalists in the Boston Comedy Festival is not nothing and I think they've really built that festival up over the years and people come from all over but like winner of this thing where I was not it was not a hometown thing for me. You know, like I think Boston Comedy Festival there's like a ton of comics from Boston every year so I kind of like you get in I think local comics have an advantage just like because they know it and they they don't have to pay to travel or anything. So you just up they apply in huge numbers.

Jeff Dwoskin 19:10

When you said earlier about kind of the places that you play and all that kind of stuff. I always I always laugh because it's like you know if someone's watching you on Facebook now you just any shark and comedian and you only post the shows where you want people to know you're actually playing Oh,

Josh Gondelman 19:24

yeah, yeah, yeah. And that's like that's so funny. I think that's like the this social media aspect of it. That's really fun. Because I really appreciate when people are like a little more honest about stuff but like I do feel like there's kind of I do feel a pressure personally to not throw venues under the bus to not bla bla bla to not make it look like I'm bad at the job. But there's definitely times where I'm just like, oh yeah, I like really ate at this show. Or like I'm doing this show. Not in cities. I don't mean like, oh, Chattanooga, but I mean like, Oh, I'm doing a show that's like on the roof of a hostel and you perform like a guy holds you by the back of your caller and you leaned over the roof and you yell at people walking by on the sidewalk, and I just I needed a set. So I said yes. Like that kind of stuff. You know what I mean? I Because I agree. I think there's like a little curating of like, oh, this person only does the best comedy clubs and the most exclusive festivals. And then, but it's like, I think it is helpful to be like, oh, yeah, I also do a show that's like, it's in the basement of a hospital for people who are waiting to who are like on heavy narcotics from surgery and waiting to be picked up from the hospital or whatever.

Jeff Dwoskin 20:32

In Michigan, we bunch of us are sitting around and we realize, Oh, we're all named Jeff. And so we did the Jeff Comedy Jam, right. Five, five Jeff's Jeff Comedy Jam. So I promoted the hell out of this show. Okay. Yeah. And my buddy, Dan Lippitt. arrives late to the show is like Sorry, I'm late. The way you're promoting this. I ended up at the theater across the street. Oh, that's funny. We're at a bar with 15 people. Yeah. And it's like he wants it the whole time during the show. He's just giving me this look like really? This

Josh Gondelman 21:05

is the jelly hommy Jam. This is the thing you've been talking about for months. Yeah,

Jeff Dwoskin 21:09

that was like that breaks the rule in the sense is because the idea of the show was better than even where it was gonna be. Because it was just it was a whole camaraderie thing. And

Josh Gondelman 21:19

Andy Sanford who I met I've met before laughing so because I think he'd come to Boston and then he was the one that was like, oh, you should apply to this. You This is worth your time. Very generous of him to think of me for it. He I think this was at laughing skull coined the term because there's the common term of like a hell gig right? Oh, this gig was bad. The money was bad. The audience's are bad. It's far away. And you have to you have to drive eight hours to this gig and they don't give you a hotel. That's the hell gig and I think it was there that as far as I know, he coined the term swell, good for like a real nice setup, where it's like, yeah, they like order you dinner from this local restaurant and the greenroom. Super comfortable. And like, it's kind of the only game in town. So they always get 300 people and packing up this little theater and I just that's kind of what made me think of it of just like the idea of like, the gigs you brag about versus the gigs that you do, because that's the job some nights it's work

Jeff Dwoskin 22:10

right. And so and I don't think people even normal people even understand sometimes what we have to go through to get that money. I remember playing a bowling alley. I'm headlining a bowling alley. That's not an impressive sentence. And I pull up it's in the middle of nowhere, like literal nowhere. I drive by 100,000 cars. I'm like, damn, but no, those 100,000 cars aren't at the bowling alley. They're at the high school across the street because their team is going to the championships there's no there is for drunk people at this bowling alley. But here's where it gets worse. This is what we have is the owners go Yeah, yeah, go ahead. Yeah, do the show. Do the show.

Josh Gondelman 22:47

Yeah. I mean, I was just talking about this last night with somebody I remember early on in my career being in Boston still and you just booked gigs. The kind of conventional wisdom is that like summers tough, right? People go to less comedy people just want to like be outside and on vacation and they're not just looking to like get like get out on a weekend night and go sit inside they want to be like up in Maine at a cabin fishing and stuff like that. And then it's like okay, well the summer is tough, and then the Red Sox are sometimes in the playoffs and that kind of kills that or like a Patriots are in the playoffs like playoff games will kind of kill a comedy night in Boston because people are like, yeah, the Celtics are in the finals. Why am I gonna go out and see a guy I've never heard of they'll joke but then then the winter is bad. Do that's the other secret but they don't because there's there's nights where the weather is so bad. They don't want to cancel because it's like, okay, we've got 50 reservations are we have their money. And if we cancel it, we have to give it back. So we need the comics to get there. So I was driving. You know, I was probably driving 20 miles an hour on the highway. during a blizzard. I saw a car. There's like a Christmas tree that had just fallen off a truck and was in the middle of the highway and I saw a car like bombing down the right lane because I was in the middle going slow. bobbing in the rain hits the Christmas tree spins out into a ditch and I'm just like, I'm risking this for $100 features, like anything like so many bad things could happen that would cost me more than that, including like my wife and I'm just like white knuckling on my steering wheel. 20 miles an hour takes an hour and a half to make a you know, to make a 30 minute drive. Just eat it in front of the 20 people that showed

Jeff Dwoskin 24:22

I have many many. I'm going to die in the snow. What am I doing? Yeah,

Josh Gondelman 24:26

what am I doing? Why am I doing this? Like people love me I shouldn't be with family and friends. But that's Yeah, I think there's so there's so much of a VAT and standup of just like those. I mean, especially like I still have it to an extent like I don't think it ever really goes away as long as you're doing it right because like there are those times at the beginning of your career where you're so hungry. You're like, I can't say no to this. I can't cancel because then I'm the guy that cancels day of even though the weather's bad, like they don't care about that. They just care that I'm the flake and So and then I mean, I think it gets to a point where where the money gets paid. I mean, I heard there's a point where the money gets really good and stand up and for some people, and then you can't cancel it because you're leaving so much money on the table. I feel like I'm in a perfect pocket where I should be cancelling more gigs. Because I'm in between those two phases.

Jeff Dwoskin 25:18

You've had a lot of writing gigs. Yeah. So you spent many, many years Last Week Tonight with John Oliver, big fan of that show. How did you how did you score that? Like, what was the process of becoming part of that show?

Josh Gondelman 25:30

So I had kind of like a viral social media thing that happened, I had a Twitter account that I started with a friend and Seinfeld today. Yeah, that's at Seinfeld today, the modern Seinfeld Twitter account, and that kind of blew up overnight. And kind of it was like, the second thing, it was like, I had laughing scholars a credit. And then this happened, I guess, two years later, maybe late 2012. And, uh, you know, year and a half, two years later, and that was like the first thing that like I could feel when I would go on stage and be like, this guy. He's corridor, the modern Seinfeld Twitter account, people would be like, oh, like, Oh, I know that, which was ridiculous. Like, very, very unexpected, very silly. But like, that kind of got me in the conversation to get to apply to more writing gigs. And so I spent basically all of 2013 applying to writing jobs, which for a late night show like that, for, you know, Jimmy Fallon, Seth Meyers, Amber Ruffin, John Oliver, you do a packet of submission materials most of the time specific to the show. And so I did probably like 19 or 20 of those in a year from January of 2013, to the end of the year. And the last one I did that year was for I got to do a tiny amount of work on Billy on the Street, which is very exciting. That was like my first Emmy kind of work in TV. And that was that was very thrilling. And then I got asked to do a second submission for Last Week Tonight in early 2014. And I did I like, I sent a another set of materials in and I was kind of I the way I was made to understand I was like ninth on a list of eight for writers. And so because I'd had this kind of experience on writing for the Internet, between the Seinfeld stuff and the like, having written freelance magazine, and like humor pieces for websites and such, I was hired to run the social media digital stuff for for Last Week Tonight. So I was there for a year. And then I got moved over to the writing staff when they had the budget to hire another writer after the first season, because first season was was very successful. And then I stayed there as a staff writer for four years. So that was kind of the process from being again, more or less a nobody to like getting my first job, which was really exciting. And I think like it was made possible by the fact that they were looking for eight writers, because they had no writers, it was a brand new show. And so your chances are just like so much higher, you know what I mean? Whether it's like if there are however many probably like a few 100 people applied for that you're going from like a one in 300 chance to like an eight and 300 chance, which is like literally eight times the opportunities.

Jeff Dwoskin 27:59

That's awesome. We have to take a quick break for our sponsors. And we're back with Josh gondola man about to dive a little deeper into his Twitter sensation Seinfeld today, and we're back. Let's talk about Seinfeld today show. I had them written down. But I didn't realize it was the origin to the John Oliver otherwise it would have gone in that order.

Josh Gondelman 28:19

Yeah, I mean, it kind of got me it like really got me into the conversation for these kinds of jobs in a way that like I've kind of been waiting, I would occasionally be asked like a friend of mine, who was a manager would go hey, Chelsea Handler show is looking for people do you want to do you want me to send in an application for you? And I go, Yeah, sure. Thanks. And then you know, very rarely did that lead to anything for me just I think because I didn't have that much practice. And then this was kind of the thing that cemented my relationship with my representatives at the time that led kind of gave me the little bit of buzz that made them go like, Oh, this is the guy that we should like, keep giving these opportunities to.

Jeff Dwoskin 28:54

That's awesome. So why did you stop? Oh, because you have like this you amassed over 700? Yeah, I think it was like 800 something 1000 followers. So it's just sitting there now. Yeah,

Josh Gondelman 29:06

I think Jacqueline and I both got busy is like the real answer. Like it kind of just ran its course where like, we did it for a couple of years. And it became like, Okay, well, how long are we going to devote creative bandwidth to this kind of like silly gimmicky thing, which is like a very fun project and I'm super grateful for what it did for us, but it is kind of like if not like a showcase for a one trick pony may be a three trick pony. And so it just kind of became like, Okay, we both are working in TV at this point. We're both developing our own projects. How much energy are we going to spend being like okay, what would Kramer what how would Kramer post or what would Kramer's Tinder bio be? You know what I mean? And there's just like, it just became less of a it became a lower priority and we just kind of stopped cold turkey instead of posting once every three months or whatever.

Jeff Dwoskin 29:55

And you won a Shorty Award for that.

Josh Gondelman 29:57

We did. Yeah, I have a behind me. It's a It's a very nice glass whale's tail because the award

Jeff Dwoskin 30:03

is pretty awesome but it's not the only award you won. So you've also won. This is so impressive Peabody award or Last Week Tonight. Well, how many did I say for Emmy Awards? The award Emmy

Josh Gondelman 30:14

Awards is correct. Where

Jeff Dwoskin 30:15

do you where do you keep those anymore?

Josh Gondelman 30:17

I have so we have a dresser in this little office that I'm in and I it's like on top of the dresser all the awards except for one a bunch of The Last Week Tonight writers I think after the show had such a is still having such a successful run that a bunch of the writers gave me to their parents to like display if they wanted and my so I there's one at my parents house that like as a compromise between my mom and dad is like behind a picture of me and my sister kind of poking over the top of the picture frame, which is like exactly how I would choose to display it. Like I think the way that it is now like with all I'm like, so flattered to have won so many awards. It's not like Oh, isn't this ghost but I do think it's like a bunch of golden trophies really dominate the decor of a room. So it feels more appropriate to have them like kind of up out of the way in the office than to like put them all on a bookshelf in the living room and like make it a conversation starter.

Jeff Dwoskin 31:07

So you have one sister you have a sister, I have one sister Do you Have you ever like considered making your parents introduce you as our Emmy award winning son Josh, but only when your sister's around my

Josh Gondelman 31:18

sister is the doctor got she has a doctorate in physical therapy, which she got like before my and she's She's three years younger than I am. And there was a brief period where she was like the one that the Oh, you're the one of the two of us that had it together. Like now it's both of us are both doing well in our lives. But there was a period where she got her doctorate and like 2012 I want to say and was like a practicing physical therapist with a job at a major hospital. And I was like really scraping by in New York doing comedy and like tutoring on the side and writing a little bit and going on the road for low money and just kind of like really hoping it was gonna happen. And so she definitely was like a success professionally before I was for sure.

Jeff Dwoskin 32:02

Alright, so for me or it's Writers Guild of America awards, a Peabody Award a Shorty Award. Finally, you've worked so hard to make your parents proud of you. Compared uses

Josh Gondelman 32:14

that's all I look, I'm just trying to keep up with my sister being Dr. Gondolin.

Jeff Dwoskin 32:21

It's funny. So when Last Week Tonight with John Oliver, is it? Is it all collaborative? Is that how you write on that show? Is there is there any? Or is there like no Josh condom on wrote this? Or is it kind of like you

Josh Gondelman 32:34

there are stories where I think individual writers have more of a guiding hand or more jokes in and like the process is not all collaborative. Like it's not like every story gets written by everybody in the room at the same time. But it is collaborative. By the end of by the time it makes it to air it has been a collaboration, there is a story that's pitch. And then it's approved by John and by Tim Carvel who's an executive producer, and there's a producer who's assigned to like call footage and really find video that helps tell the story. And then there's a producer that works on the research for the kind of, you know, like looking to see like, what is this story? Really? Is it what we think it is? Is there a surprising twist that we don't know about? Is there? Are there common misconceptions that we don't want to hit? What can we factually say? And then there are usually two to three writers assign, especially for the big stories, and the writers write drafts independently, but like well in conversation with each other. And then And then John and Tim, edit and revise and make new asks of you know, the rest of the team on the story. And the writers take another pass and then the writers room will punch up jokes where they're like, you know, this joke needs a little something more or like we need a new job because we added a new factor or piece of video footage. So it is really collaborative, even though the work is a lot of the time kind of independent, like when you're writing a draft, it's like a couple days to outline by yourself other than a couple of meetings a couple days to write a draft by yourself other than with a couple of meetings it's not you know, the 30 rock writers room I think that's like the kind of that are though, you know, wherever Dick Van Dyck or you see a bunch of people just like what about this I bought this thing so it's even though it is many points in the process, kind of solitary with your writing and your outlining and all that and like looking over materials and kind of like picking what you want to include in the story it ends up being very collaborative because there's so many different people working on at the same time from different angles like you know, different responsibilities on the staff and then in the writers room writing jokes together for a long time and you're you know, in the writers room writing jokes together like over the weekend because the show airs on Sunday so that is like that's like the part that feels the most collaborative is just like being in the room with the other writers which is very fun.

Jeff Dwoskin 34:37

I did notice on your IMDB you were on at midnight. Yes, I was obsessed with it at midnight because that was like I think 1213 times and made it to the final tap time but I never won and you know Jack Ma right where they fit in

Josh Gondelman 34:52

with Yeah, on the Twitter and stuff like with the social media, so many on social media

Jeff Dwoskin 34:56

and what kills me is my buddy you know, who also would like not a comedian one frickin three times three times so and I've other friends that one multiple times and I could never I don't always get them like oh this is it this is my night wake your weight up I'd wait up watch it and it was it was never made at some point I'm like this is somebody's This is personal

Josh Gondelman 35:20

I got to do it once and I like flew out I think I flew out and back in a day maybe like definitely flew home after the taping right I so I could be at work at Last Week Tonight. The next day. It was it was really fun. They I got to write with. I think Chelsea Davidson was the writer that I was paired with who's great. And I was on with Randy Leakey and Kyle Kinane. So it was like great to see people that I really liked, and that were really funny and like play with them. And so it was like a good vibe for the taping. It wasn't just oh, I don't know these people. So I don't know what way we can interact. You know, I think it's sometimes tricky. Even on a podcast to be on with a bunch of people in your like, I don't know, the the dynamics, I don't know people's comfort zones, not in terms of like saying edgy, risque stuff, but just in terms of like how much give and take there is how like, fake competitive to be that kind of thing. And so it was nice to be on with people that I was like, Oh, I know that these people are very funny. And they won't. They're not taking it intensely. Seriously. They're not like trying to crush me. And they know that if I'm joking around, it's not because I'm trying to usurp them.

Jeff Dwoskin 36:21

writer and producer for desus and mero. on Showtime. Did you leave Last Week Tonight for this role? I did. And then what made you kind of say, Oh, here's here's the new opportunity. I know, they probably after five years, you're right, ready to make a move? I imagine.

Josh Gondelman 36:36

Yeah. I mean, I think that I'd had such a great and fulfilling run at Last Week Tonight. And I've worked with people that I really love and admire and a lot of people I'm still in touch with and just like think are just such great colleagues and people I learned a lot from and after five years for with the same job title, I felt like I was still getting better, right? Like I could still improve as a writer for that show. But there weren't really like opportunities to learn fully new skills, like the writers weren't gonna get opportunities for the most part two, like produce something that out in the world, like a sketch or something. And we wouldn't, we weren't getting a lot of opportunities to like, look at that edit of pieces, like, you know, little bits here and there. But I really wanted to be more hands on with that kind of stuff. I think if I had been at that job and been like, this is the only thing I ever want to do in comedy. I wish I could stay here for my whole career. You know, I could say here 20 years, I would, but I think I was like this is really pretty in the grand scheme of jobs. It wasn't an ice road trucking, that's more like stand up. But I all the comedy is like pretty light in terms of like physical labor. But I do think like it was a pretty rigorous job in terms of like really engaging with the news, which is bad a lot of the time and like really staring it down and writing into it. And I was like, you know, if I could move on to a job that like leans away from just the devastating truth of the world so that I don't have to deal with it professionally, every day, as much as in addition to like coping with it as a human being with a heart and a brain. I would like to try that for a little while. And so I also wanted, I didn't want to leave just to leave, like I didn't want to leave and like get a job, you know, writing and producing, unlike VH ones top farts of the 90s or whatever is the fake show I always use so I got this opportunity to interview with Jesus and marrow. And I was like, Yeah, this sounds really exciting. They're so funny. It would be a writer, producer job like kind of a supervising role. I'd learn new skills, I would work in kind of a different tone. And it wouldn't be like I got a couple of offers while I was still there at Last Week Tonight of like, Hey, we're doing this show that we want it to be like John Oliver show, but for history, or we went to like John Oliver show, but for science, and I was just like, I don't really want to do that. Like I don't want to like chase this show somewhere else. And so it was a perfect opportunity to do something that is like with hosts I really like and enjoy and think are so funny and talented, but with a totally different feel to my last job.

Jeff Dwoskin 39:00

You have an old project that I loved wiki what? Oh, yeah, that was really fun. That was really funny. I was are you a sports guy?

Josh Gondelman 39:10

I am a sports guy.

Jeff Dwoskin 39:11

You had Kate Upton on your show? Yes. Love Kate Upton. She's from Michigan. Yeah. So this is how much I know about sports. We're I'm in Birmingham, Michigan. I'm looking at we're in a restaurant. I look over and I say to everyone. Oh my God, look, there's Kate Upton, so that must be Justin Verlander.

Josh Gondelman 39:29

Oh, that's so funny. Yeah, cuz he was still pitching for the Tigers. Yes, thanks. Well, this

Jeff Dwoskin 39:33

was when I talked to her. Yeah. Yeah. She was talking about being a Tigers fan. Yeah,

Josh Gondelman 39:37

yeah, she was very nice. She had had like, I think she was just like doing presses pretty exhausted. But her dog was like the most well trained dog I've ever encountered this like beautiful 60 pound boxer. And Kate was very gracious like, had no reason to do this thing with me that like I was doing I guess it was like technically for Esquire but it kind of just like lived in her digital ether on YouTube or no, you know what? It was it was Facebook, like, produced it with Hearst as when Facebook watch came out where Facebook was like, we're gonna make our own shows. And this was like in that and they did fine. They weren't like, it wasn't like, Oh, he's got like 200 views. It was like, oh, a couple of them were, you know, 300 500,000 views, but I think they were just like this is not worth the money we spend on it. So we only made five ever. And then they were like they invited me after we wrapped that first run of five. They invited me to this big like Hearst digital launch and they like introduced labor like Josh Coleman, who hosts one of our shows, and I was like, Hey, this is fun. We'll keep doing this and then never heard from me.

Jeff Dwoskin 40:36

She was a good sport. She looked like she was having a good time.

Josh Gondelman 40:39

She was a good sport.

Jeff Dwoskin 40:40

You were TJ Miller was on episode, I had the opportunity to emcee TJ Miller once and that guy's hilarious.

Josh Gondelman 40:48

It was a pretty chaotic interview. And he's kind of like, I know he's there. There have been some, you know, allegations and stuff that it's like, he seems like he's a kind of a troubling figure. But the interview, I think he was he recognized me from stand up like we'd been on shows together. So I think he was like, he turned the chaos down to like an eight out of 10 instead of his normal 12. But it was like all over the place. It was like a very intense like, it was the first one we did. So it's just kind of sitting there being like, oh, okay, that was your first episode. Yeah. And it was I'm trying to think it was it was TJ and then it was, um, I don't remember the order. Exactly. But John Bradley from Game of Thrones on Game of Thrones was awesome. He was the most fun interview. And then Lauren skilling Jr. from the wire and walking dead. He was on. And then Kate and Adam Kahn over and I think that was the full run.

Jeff Dwoskin 41:44

That's awesome. You have a lot of no longer active amazing projects.

Josh Gondelman 41:49

Oh, thank you. I mean, like, I think that's just a function of like, I've gotten some really fun and exciting opportunities over the years. And I've been doing this for like an embarrassingly long time.

Jeff Dwoskin 41:58

Let's Let's pitch some of yourself though. Real quick. You have two books. Yeah. Three albums. Yes. All available Josh randleman.com, or Amazon's or all that kind of stuff. I'll put links. Yeah, I'll put links in the show notes to each one of them. So you have that. But you also have an amazing podcast make my day podcast to comedy game show.

Josh Gondelman 42:17

Yeah, that show is so fun. It's the premises, right? It's a comedy game show where there's only one contestant, if there's more than one contestant, they're playing on a team. And so the contestant always wins it's very low stakes in that way. And each contestant sets the game's all time high score. So the high score is just escalating week after week. I think the first episode was like 36 points. And now the most recent one was like 1700 points.

Jeff Dwoskin 42:44

It's really great. So I do encourage anyone it's a good pick me up it's meant to bring positivity in the world. One of the one of the goals is to bring happiness to Josh

Josh Gondelman 42:53

Yeah, I just want people to be delightful and like I really just want it to be like I always kind of feel like that. I don't want to make entertainment that is like fun in ignorance of how difficult to place the world can be a lot of the time for a lot of people I kind of want to do stuff that is like fun and light and enthusiastic in spite of that, which is a slight difference, but I think it's like the difference between being like oh, yeah, it's gonna be fine. We're all fine like this. The bad stuff is like you know, it happens but it's for other people or like it's not that bad and being like, yeah, things are bad and like let's try to make them a little better and a little gentler and kinder

Jeff Dwoskin 43:31

awesome. So much Josh condom and you can bring into your life ladies. Josh, where can people keep up with you on the socials?

Josh Gondelman 43:38

I'm at Josh Gondolin G O N D E L man on Twitter and Instagram. I think I'm legally too bald to be on Tik Tok. That's where you can find me on social.

Jeff Dwoskin 43:48

So everyone check out Josh condiment.com. And all of Josh's albums are streaming everywhere can be bought everywhere as well. Josh, thank you so much for hanging out with me.

Josh Gondelman 43:59

Oh, thanks for having me. This was a real treat. It was really nice to chat.

Jeff Dwoskin 44:02

All right. How amazing was Josh Gondelman are the nicest people in the world and happens to also be super hilarious. Head on over to Josh gondolin.com. Check out his albums, all his goodness. Do yourself a favor. Get as much Josh condiment into your life as you possibly can. You heard it here. You heard it here. Can't believe it. But episode 194 has come to an end. I want to thank once again, my special guest Josh Gondelman. And of course, I want to thank all of you for coming back week after week. It means the world to me, and I'll see you next time.

CTS Announcer 44:40

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Transcribed by https://otter.ai