Episode 19 | Steve Dildarian

This is the How to Write Funny podcast. I'm Scott Dickers. And today I'm speaking with Steve Dildarian, creator of the HBO series The Life and Times of Tim. Curious to know how you got into comedy. into comedy. Yeah, before you ever had your TV show, before that was a glimmer, that first film that you made that led to it. Did you do comedy in school? Did you have any kind of inkling growing up? Do you have a funny family? Or, you know, what was your sort of relationship with comedy early? It's funny. I didn't even realize it as it was happening, but I definitely, in school, even going back to when I was like 10 or nine years old, it was the one thing I was always singled out for in class, was creative writing. And like when I was 10, they sent me to a young author's convention. They picked one boy and one girl from the school because I wrote this funny poem.

And so looking back, things like that. And then when I was like 12 or 13, one of my English teachers pulled me aside after class and said, your essay was so funny, I took it home and showed my husband. And at the time, I remembered it. But later on, when I realized I was actually going to do that for a living, you know, it kind of took on a greater meaning, these little moments of kind of encouragement. Yeah, that's awesome. So did that, that was just a small part of your life that was a kid. It wasn't like this lit a fire under you. This was more like, oh, okay, I guess I'm good at this. Were you thinking of doing something else for a living at that point? You know, I didn't have much of a clue. But in high school, though,

By the time I was like 15, maybe, it was pretty clear that that was the only thing that I seemed good at. I wasn't the best student. I didn't have any... family history that would be steering me into any given career so when I looked around them it was kind of like an obvious not even a choice as much as my only hope you know I was like you know writing comedy seems to be the one thing I might be able to do and so I started looking at colleges with that in mind and originally wanted to write TV right out of the gate but uh ended up kind of switching my major once I went to school and got into advertising mostly because it just seemed easier and closer to home I was in Jersey going to New York was more doable in my head than going to Los Angeles was so Got it. So had your sort of comedy style, the stuff you found funny, was that starting to form in high school and into college? Or was it pretty much just all over the map? You were just trying to be funny? Or was there like a voice, a Steve Delarian voice? Yeah, it's funny. I think there always was because, you know, tone of voice is really everything. And it's not the kind of thing that would change. You know, the way I might have written things or the reason some of my early childhood things were funny was, you know, pretty darn similar to what I do now. It's just a kind of dry, deadpan take on things and a slightly absurdist point of view. And yeah, it really...

That's not something you learn or you might get better at executing it or turning it into usable work. But the core thread to it all is really the same. Yeah, I remember one similar thing. It was one of those moments. It was in high school and we had to give a public speaking, you know, kind of speech. And I was terrified out of my head and couldn't even deal with it. And so beyond there because I was pretty quiet in high school. And my way out of it was with writing. You know, I said, I'm going to write this little questionnaire. So when I get up to get my speech, I'm going to hand it out to the whole class.

And so I did this and there were funny questions with funny answers. And, and the whole class, when I got to get my speech, they're all looking down at the paper and laughing and, and I felt so good and it made the whole thing doable. And it was a real moment, you know, looking back where it's like, wow, writing can be my way to connect to, to show people I've got a good sense of humor and to make life easier in a lot of ways, you know? So these, these moments that were kind of weird little passing things at the time, I kind of always look back and they get pretty profound actually, you know? That's awesome. Yeah. I mean, obviously writing is a great way to connect with people, especially for, you know, people who are shy or awkward because you're getting inside somebody's head and you can really, you know, with a laser focus, like share your thoughts. And that's one thing people love about reading comedy. And if you had that kind of style that was very personable, you know, very idiosyncratic style, that must've felt really good too. There's a lot of people, you know, you develop, you know, you do it for a reason. Some people are funny just because they're funny. Most people are the better ones, I think are funny because they needed to be funny.

You know, they developed it as usually a defense mechanism or whatnot. But for some reason, there's a need to go there, a need to make people laugh this way or that way. And, you know, I think when you don't, it's a tool at your disposal that most other people maybe don't need or, you know, they don't have to go there. For me, it was a very organic thing to just rounding out my personality. And do you think that was what your need was, was social connection?

I think, I mean, who knows if there's if someone's personality, their instinct is to be quiet. So if they're at a lunch table or in a classroom, you're probably not going to raise your hand. You're not going to do this. As a result, you're not going to be that popular or whatever. But if you're when you write things down, you do get that reaction. You know, that's a powerful thing. It's like suddenly people like you. Suddenly people think well of you. You know, it's that's evolution at work. Suddenly you're going to write the great comic novel because you know what what the end result of that is. People love you.

I mean, you can say about any one of the arts in any way. Usually you do it for a reason. You don't just do it. It's not just a fun hobby. You know, you're compelled to do it. Yeah, you get obsessive at some point. Yeah, totally. Did you get obsessive once you were, and that's usually when it happens for people. Not coincidentally, I would say, because that's when hormones are really at their peak. Like in that transition from high school to college, did you have an outlet, an obsessive outlet for your humor writing?

I don't know about that. I actually didn't have too much of an outlet other than I did start to develop a little reinforcement that I'm going to be good at this. Like my teachers, right from the word go, were very encouraging and always singled me out. So it wasn't just me sitting in my basement in New Jersey, you know, hoping I could do this because a few teachers encouraged me. Suddenly it was a little more real and a little more legit where college professors are saying, all right, I want to do it like Steve did. Well, yeah, you've been to author camp. So you were serious. Yeah, exactly. But yeah, once I got to college, I became.

obsessed only with And embarking on a career. And once I thought advertising was the way out for me, yeah, I was, I don't even know if I'm obsessed with the right word. I was just extremely enthusiastic and spent a lot of time working on it and taking internships, driving up into New York when I could and taking night classes at SVA. And it was very driven at that point. You taking like writing classes or? Yeah, yeah. School of Visual Arts in New York. They had like night classes, which were great because it was with real teachers that were actively winning awards in the business. It wasn't, as opposed to, you know, not to knock my college, but it was in South Jersey and the teachers.

had been out of the business for years, and as great as they were, it was a little more of a theory you're learning. Where did you go to college? Glassboro State, then in South Jersey, by Philly. So the idea of going to Manhattan... And learning from teachers that had just won a big award that year, it was a pretty exciting thing. So I would drive up every Tuesday night and do my classes and work around the clock at night getting ready for that. So it was a very busy time doing that and doing internships and going to school. Wow, yeah. So you get out of school, you have some sort of degree in communications or marketing or something? Yeah, yeah. So communications, marketing degree, which is nice, but it's really not that relevant to the real world. Nobody cares, ultimately. Yeah, creative jobs. So I asked a bunch of...

people and friends I had to go about it and it was clear that you need a portfolio you need you know and that's when the school visual arts stuff I started during junior year college but really got into it after college and uh spent a good year after school or not quite a year but uh eight months just working on my portfolio. And yeah, School of Visual Arts was waiting for me to do that. They sort of taught you how to put one together, how it should look and everything? Yeah, it's real basic, just how to think creatively. And at that point, it was really just print-driven stuff. It was headline-to-visual, how to make memorable, clever ads. Even though you end up doing TV and radio and stuff later, they kind of teach you in print. I think that's still more or less the norm. But yeah, it was just making a portfolio. And that book at the time, which was laminated ads that you would flip through in a black case.

You know, that's everything. Your portfolio is everything you've got in the world. You go to advertising agencies and you basically are saying, this is what I'm capable of. That's how that works. Yeah, very much. Creative resume.

Yeah. And that still is, you know, tonight's the same thing, but people have the ability to shoot their own little commercials and they just post to their website. So it's not really any different. But yeah, it was making that portfolio. And whatever I did, it was enough to get me in. It wasn't like a dream job or anything, but I got hired at a big agency in New York called DVDO. And I was a junior writer working on Gillette, like pretty terrible creative stuff, but it was a real job. I got to go from my bagel shop in Hoboken to having a real job on 6th Avenue. It was pretty exciting. And are you still living in Jersey and commuting or do you get a place in New York? Yeah, well, you know, I moved.

further up in Jersey. I grew up in East Brunswick in the central part and then got my own apartment with some friends, you know, in Hoboken. So I took that job while I was just scrapping to pay the rent. I was working at a bagel shop, delivering radiators, caddying, you know, all kinds of jobs. Delivering radiators. Why didn't you pursue that? Oh my God. I had so many odd jobs. I can't even remember them. The radiators one was particularly bad because it was after college. You know, I'm a college grad. I've got my degree, but I'm trying to work on my portfolio. So, you know, just taking whatever job I could do. So I took that job at Fingers Radiator.

which you know every other guy there was like a you know in rehab or an ex-con or just a troubled youth in some way and uh and then there's me and college boy yeah it was just you know on one hand i didn't care but on the other hand it's kind of you start in the back of your head saying am i going to be here in five years my head says it's a two-month summer job but there's always that fear that this is never going to get off the ground so your book which was um no ads that had been published they're just as you created for the book exactly they land you this job at bbdo and it's um What kind of an entry-level job? Are you literally on the creative team, or are you more of a coffee runner, or what's that job? I was a junior copywriter, so it was a legitimate writing job. It was just the lowest job in a huge agency, so you're not going to get any great assignments. You know, the experienced people, they were doing Pepsi Super Bowl commercials and, you know, Doritos, whatever the big brands were, Pizza Hut. So I'm sitting there doing, you know, print ads for Gillette, you know, talking about the best a man can get and redefining, you know, men's shaving. It's terrible, terrible work. You're in the door. You're getting to know everyone and volunteering. So me and my partner, Matt, we would...

Just volunteer for every assignment there and work crazy hours trying to sell something for Pepsi or 7-Up or whatever they had. Yeah. Did you get hooked up with him at the agency or did you guys come in together? He was already there. He hired me. It was a funny story because he hired me to work on Gillette as his partner. He'd been looking for a partner and didn't find anyone he liked. And then he liked my book. He asked his boss who was in LA on a shoot if they could hire me. And I think there was some weird miscommunication where he gave some kind of positive feedback, but in his mind, didn't say yes. My partner, Matt, took it as a yes and officially hired me. And I came in and started like two Mondays later, wildly excited. And on my first date, this guy is like, who are you?

What are you doing? And my partner, Matt, was panicking. He's like, we hired him. He's like, we hired him. And that's my first day on the job was wondering if I'm going to be politely asked to walk back out. That's great. Yeah. So I mentioned there's a lot of people like you at agencies, big agencies like that, who are young. They've just got their foot in their door, and they're just doing all this kind of extracurricular work. And that's kind of the culture of an ad agency is people just working really, really hard to try to rise up, right?

yeah definitely it's pretty like um there's a lot of opportunity because there are entry-level jobs to be had where in theory you're doing what you want to do um and then it's just the attrition rate of seeing who who makes it past that first year that second year that third you know and we were lucky enough to slowly get some traction we took on a bunch of freelance assignments that you know were some funny ads and then got something else our big break was we did a freelance thing for cliff freeman who was like the hottest thing going at the time because he did like all the little caesars pizza pizza stuff and uh we got hired there and that kind of everything happened fast after that because it was such a great place to be so yeah tell us how you got there to because eventually you got to be doing the really big stuff that you that seemed kind of out of your reach when you first got hired there yeah so that was a pretty quick trajectory for you and was it all at the same agency or did you move Yeah, well, I mean, the quick version of it is we were working at BBDO, like I said, doing the terrible Gillette stuff. And we did this freelance thing for a pitch for Rolling Rock beer at Cliff. And we didn't win the pitch, but they loved our work. All of a sudden, we were on Cliff Freeman's radar. A few months later, they called it at Christmas time and said they wanted to hire us. So we took that job. And, you know, once we were in that door, it was like, it was a pretty great elite place to be at the time. It was like a creative department of eight people doing some of the most award-winning work out there.

So it was a huge, huge deal. And you kind of knew it was just a matter of time until you started doing well. So for us, it was like six months in. And all of a sudden, we sold three Little Caesar spots and three Staples spots. And they started winning awards. We won all the biggest awards you can get, like the gold lion can and the gold one-show pencil. And for a 25-year-old kid, it was pretty amazing to be winning those. Yeah. So let me pause. Now that you're sort of at the peak of glory, well, at that point, the peak of glory in your advertising career, I'm curious to know if you were...

fulfilled by that as a comedy creator, if you found that to be a good outlet, if you felt stifled ultimately by the fact that you were doing corporate-sponsored advertising as opposed to more just purely creative-driven comedy? It's a funny thing. I've always been a little just discontented with whatever I'm doing because I want to be doing something bigger and better. And the TV stuff at that point was in the back of my head because my advertising stuff was full steam ahead. But what I did want to do was write fiction. And I started writing this novel. So it was a weird thing where I was 25 and...

doing pretty great you know for me especially just I had no expectations going in so I was already succeeding beyond my wildest dreams and uh but really just feel like I wanted to be a legit writer writer and I quit that job and spent four months I went down to Key West for two months and uh started you know not started but tried to finish writing this book that I've been working on at night. So you took time off of your job to do that? Yeah I left I left the job and said maybe I'll come back in the fall and because I was so I was you know maybe a little too confident I was a just cocky 25 year old kid who's just already winning all these awards. thinking I could do anything. Yeah, you've got this advertising thing nailed. Now it's time to move on to the next thing. I was a little misguided, but it was a young, ambitious, excited 25-year-old dude who wanted to write a novel. And so I spent four months doing that, and it didn't work, which in retrospect is not a surprise. I didn't have the maturity or the ability to do something like that well. So I tinkered with it for a few years after that, but I kind of realized it wasn't maybe my strong suit. So I went back to advertising, but not to that agency. I got a freelance job in San Francisco.

Goodby Silverstein Partners, which back then was also the hottest thing going because they had just launched the Got Milk campaign, which was obviously a very popular thing. And, you know, Sega was big at the time and Norwegian Cruise Line, all these things were winning all the awards. So I got a job there. And, you know, at this point, I had some stuff under my belt. So I came in at a higher level. Now, did they pair you with an art director there? Do you still have your guy? Yeah, yeah. Todd Grant. He was a good, great thing for me at the time because he was just everyone there was maybe.

I don't know how to say it, but it was a different world. The world of San Francisco advertising just had a different tone than the advertising of New York. And it felt like a more, I don't know, maybe a smarter place and a little more artistic sense of what an ad could be beyond just being funny. So I definitely was in a peer group that I needed to impress. I needed to catch up, if anything. So it was a good challenge. And maybe a year into that, we sold the Budweiser stuff. And among other spots, we sold this spoof of the frogs, which was doing the Budweiser lizards. And it was really just a lark of a thing.

But we shot it and it caught on. And before you know it, it ended up being the biggest thing in my ad career because we got on the Super Bowl and stayed on for several years. And it was, you know, a big thing for Budweiser, which is as big of a platform as you can really get in advertising. Yeah, no, there's multiple Super Bowl spots. Right. Yeah. Nothing bigger. Yeah. And winning awards where it's like popular, but reviled in the ad community. Kind of did both where we were winning all kinds of awards and being popular. It was pretty much a dream.

Dream scenario. Right. And then what happens next? Are you getting the bug again to break out of advertising or do you stay with it this time? It was funny because it was yes and no. It was so popular at the time that I was lucky enough to get people calling me. So someone from Disney called and said, we love the work so much. If people want to do TV, come down and we should talk. So I said, that's very much what I want to do. Let's talk. So at that point, I was like 28, 29. And I took a trip to LA and met with them.

And they hooked me up with agents and production companies and everything. And ended up not leaving my advertising job by any stretch, but sold a pilot to ABC. So they paid me to write a script. And it didn't get made or get on the air, but it was a big, big foot in the door in that world. And so for the next five years, I would do that pretty much every year. I sold another one to CBS the following year. Are these like sitcoms? Are they animated, like animal-based stuff, based on some of your commercials? They were human beings, live action human beings. Because I know how they like to put people in pegs and show business.

No, one of them was. One of the five was animated and animals. But the rest of them were real people. So sitcoms. Yeah, sitcom, live action, whatever. These are your ideas that you came up with and pitched and they bought. Yeah, so I would do that pretty much once a year. Maybe I skipped one year in that stretch. But for a good five or six years, I would sell a pilot and write it while I'm doing my advertising. And none of them ever got on TV.

Actually, it was pretty established in the world at that point because all the networks knew me and liked me and wanted to keep hearing things. I just hadn't succeeded in getting something on yet. Yeah, no, it's crazy. A lot of people make a good living producing work and their career continues to rise without ever creating anything that people see. Yes, yes. And I was in a kind of weird...

kind of a middle ground that a lot of people don't experience because I was lucky enough on the advertising side to have the dream scenario I had this TV campaign that was ongoing that everyone knew I could literally go into any any bar in the country that people would know and like my work you know what I mean it's like that's the dream if you can ever sell you know Seinfeld there's nothing I'm not comparing the two but it's like you know what I mean like that's the end goal everyone to know and like your work and in the advertising realm I had it so it was it was a weirdly like a lateral move the idea of selling a show that maybe half is good and get half the attention and get canceled you know right and people ultimately don't care like the people in the bars you know to them a funny thing is a funny thing whether it's an ad or a sitcom doesn't matter to them yeah yeah yeah so it was interesting spot to be in and it's the reason i never left advertising because i had it pretty good um but then for whatever reason i was a stretch of time where i just got a little fried and a little bored and i was kind of not that motivated at the agency anymore and a little bummed out on what some of the pilots that weren't going forward so uh

For whatever weird reason, I started painting in that stretch. And the painting, it all was this weird kind of blur of a stretch of time where I started doing things out of my comfort zone. And I started drawing and illustrating. And I started learning to edit. And I started doing voices. And it was all uncharted territory. And it kind of just coalesced in this short film. Me and my girlfriend called Angry Unpaid Hooker. And it was just completely on a whim and silly. Not something I was looking at as a strategic career move. But was it a plan? Did you work on all these things to get to that point? Or was it really just an exploratory R&D phase that ended up kind of randomly at that?

Everything was completely random. I had started to draw because I started to paint. The painting was purely for me. It was fun, and I had a few little gallery shows in San Francisco. Not get real galleries, but friends would show up. It was enough to take it seriously. My painting was a fun part of my life. So then we did this weird little web series for Budweiser called The Rejected Ads, which needed some illustrations. What year was this? They were doing a web series? It's like 2005 or so. Okay, so just right when web video was starting to become a thing that most people could actually have the bandwidth to see. Oh, exactly, yeah.

So doing the Budweiser stuff, it was just for their website, but it won some advertising awards and it taught me to scribble my own little style that could be turned into some form of animation. Oh, so these were your drawings that were made into this web series? Yeah, they were really six-figure-y kind of drawings that we used as if the creative team was doodling when they were coming up. Oh, like storyboards or animatics or something? Yeah. Okay. Yeah, so we made those and I did the voice of one of the two characters, which was pretty much the first time I had done a voice or anything. But that was just that and we did it and I never thought about it again. Was it just your own voice or like a character voice you were doing?

You don't do characters. Dial it down, but it's always just this. We did those. How many of those did you do? Probably a dozen of them. They were minute-long little things. But yeah, after that, I had the idea for this short film. I just kind of sat in my notebook for a year. I never did anything about it.

Then one day I just said, let's try to see if we can animate. And the early stages of it, it was so absurdly backwards and nonsensical. I drew the characters on the couch with the characters on them with a pick pen, went to the art store and bought these markers and tried to color it in myself with markers. And I didn't even know how I was going to turn that into something else, but it took me like two days to do. And my girlfriend looked at it and was like, what are you doing? You can't do anything with this. So she took it away from me and separated the characters and made it in Photoshop and rebuilt it.

So they could actually be moved and animated without recoloring and redrawing everything. I really had no idea how I would have done anything with what I was doing. It was literally trying to make five frames of animation. So once she showed me how the files could work, it was a real eye-opener where it's like, wow, let's go for this. And then using iMovie, we would take her replicated versions of these and literally just kind of like a flip book, put one frame after another.

And we were shocked when you played it in iMovie, it actually looked like they were talking or crossing their arms. It was like reinventing the first time a flipbook was ever made. And you had discovered animation. Exactly, it felt like it. So yeah, with that, it was so encouraging. I recorded the voices and spent a few months making this short film, which was painstaking because it was frame by frame. It was asking for every permutation of a frame. I need the wide shot with Tim's legs crossed, with Debbie smoking, but Tim blinking. Now give that to me without him blinking.

And so you'd re-export frame by frame just to make it look fluid. And it was pretty silly in retrospect, but we made a six-minute short. And it's just a labor of love. You have no aspirations with it at this point. I mean, I wouldn't say no aspirations. It's just naturally I'm always trying to see what I can do with something. But I certainly didn't think it would be a TV show. But we did say, let's send it off to film festivals. So we sent it to like five or six film festivals. And we only heard back from two of them.

And one of them was the comedy festival in Aspen that HBO used to put on. And the other one was out of Palm Springs. And the reaction was just amazing. I couldn't believe how much people were into it. I mean, I felt like it was funny, but I was definitely surprised at how funny other people thought it was. Because, you know, both of them were like, the HBO, the Aspen one, they called me and said, we don't have a category for animated shorts. It's just best animation. But the judges love it so much, they want to create a category to give you an award. So I flew to Aspen, and that was just an incredible kind of whirlwind of a weekend. And then at the Palm Springs Film Festival, Jason Reitman was the head of the jury that year.

They gave it the high five to lo-fi award. But it was pretty great. And that was happening while my agents were already starting to send it out. And then it was just like a blur of a kind of, it was just nothing but positive, exciting news. Everyone wants to buy it. Fox wants it. Warner Brothers, go meet them, go meet them. And it happened pretty easy and pretty fast. Now that short that you did was in a long succession of people making animated shorts that get people in the business excited and want to make a show out of it. Like the South Park guys did their Christmas video greeting. Seth MacFarlane did a video that got Fox excited to do Family Guy. But now we're in the era of web shorts when it's starting to get really crowded with all these animated shorts online. And a lot of production companies are producing animated shorts to put online to kind of see if they can...

artificially generate that kind of excitement. So how do you feel like your trajectory took advantage of that system? It's interesting. It's like, you see with a lot of things that aren't animated, the pool of people making the stuff is definitely expanded. There's a million people making animated shorts, live action shorts, whatever.

But the pool of people that have the capability of making that a TV show, if that's the goal, that hasn't changed that much. So, you know, the weeding out process happens pretty quickly. Just because there's a million funny animated shorts doesn't mean all these people are going in and getting pitch meetings at TV networks. Yeah, most of them don't even have agents. Yeah, yeah. So it's not that much of a factor. You're still dealing with the same, you know, probably...

fewer than a hundred people. I don't have people that would have an agent that Fox or Comedy Central or Adult Swim actually want to hear from. Maybe it's more than a hundred, but it's not a huge number. It's not the hundreds of thousands of people on YouTube, you know, with every little shorts that they want to make. So having that, I don't even know what to say about it. It's not, it's a, it's kind of the same that it's always been. I think if you're a writer that can, that can go in and sell something.

That's what they want to hear. If you have a short, great. You know, cool. Maybe we've jumped the gun and we don't have to, you know, might sell a little easier, but you can sell just as easily without that short if you're the right person. Right. Your short just served to generate some heat and some excitement. And if you didn't have all those connections, you still might have generated that heat. And that just verifies that, oh my God, this is a guy we really want to work with because he can generate that magic heat. And he's been through the process. He kind of knows our system. Yeah, sometimes that stuff can work for you and against you. Sometimes if you have the short...

It can make someone say, eh, we're not interested, where they might have been intrigued. If it was just, here's the person, here's their background, here's the idea. Sometimes the intrigue of an idea gets very exciting in those development rooms. But then you lay your cards on the table, and it's like, eh, we don't want that. So sometimes making it can hurt you. Sometimes it's the only way in. There's really no rhyme or reason. So it's kind of like, I don't really have a strong opinion on that. It's like, if it works, it works. If you make it, you make it.

It's case-by-case, you know? Yeah, in that case, it worked, and your agents got you... Was it like a bidding war to buy this project, or what was it? It was definitely that type of vibe. There were multiple people interested, and I think what happened was that the highest bidder kind of won early on, because that's always the instinct, at least from the agent's point of view, is to go that way. So when they knew that Warner Brothers wanted to do it, and Fox wanted to buy it...

that was just it answered itself we just went that way i don't know whether it was the right way or not i don't know but that's what we did um but when they passed on it a year later after making a pilot then you know comedy central wanted to do it and uh it's kind of a long murky story but we actually went into production with mrc with no network attached because they knew we'd have multiple bids they were just there's a lot of good buzz around it so we we hired a staff and got office space and started making 10 episodes with no network attached to buy who was funding that Okay, interesting. And then the pilot and those 10 episodes, were those 22-minute shows or were they the 15-minute shows that you ended up doing?

It was the short one. Even though we were set up and getting started, HBO made an offer and we had a meeting with them pretty early. I think they knew they wanted to do it and they'd rather get involved soon so they can put their stamp on it and influence the development. No one wants to buy it after it's made. It wasn't more than a month into the production when they said, all right, we'll do this. That was a good thing for you.

It was the best thing in my life. I mean, yeah, HBO, they're renowned for how well they treat creative people. Oh, yeah, it didn't even seem real. It seemed like a dream, you know, making 10 episodes for HBO. It was crazy exciting. So they're helping you develop it, but you also feel totally free and supported? Yeah, yeah, they're the ultimate place for that kind of thing because, like you said, yeah, there's more freedom than any China will ever give you. I mean, these days there's probably more. It sounds like, you know.

a lot of the Netflix, Amazon, Showtime. There's a lot of places that probably give more of that type of freedom. Yeah, that may be true, but they don't have the prestige. Yeah, yeah, totally. So it was, you can't hope for much more. You know, it's the ultimate. They let me do my thing. They stepped in when they needed to. They were really helpful in just making the work better, making the writing stronger and putting me with the right writers, the right actors. They've got access to all the best talent. So, you know, try to take advantage of that as much as possible. So the production team that you had putting the show together,

From what little I know about it, it really wasn't that much more sophisticated than when you were sort of figuring out how to do animation back at home, right? Well, you know, in the beginning it was, and kind of against my will, everyone slowly started making it a little more polished, a little more professional and a little better. And I, at the time, I think naively just wanted to hang on to my, you know, completely raw infantile looking shorts. And it's, I don't, I'm glad people pushed me out of there because, you know, you want it to look. I don't know. You don't want to feel like a student. It should be broadcast quality, at least. Yeah, exactly. Yeah, I was arguing with people to let me make it in high movie. That's just, that's just idiotic. I mean, South Park did lower the bar, and I don't mean that in a bad way. But, you know, really good production value is not necessarily a help to comedy. Sometimes low production value is a lot funnier, and South Park really proved that. And, you know, your initial short was obviously very funny to people, even though it may have been a kitchen table produced. So how did you somehow infuse your new HBO-sponsored production with and retain that quality?

Well, I think, I mean, right to the end, I think it's still retained the essence of the spirit of the short. It never got that slick. I mean, some people might look at the first episode and the last and not see a difference. I see worlds of difference. Maybe I'm hyper sensitive to it.

A lot of people, it might be lost on them what I'm even reacting to. So we certainly never crossed that line where it's like, oh, it's so good looking now. We never got that far. But the more important thing is for the infrastructure of the production to get professional because that'll kill you if you're just bogged down in not being able to execute. You know, TV show has no choice but to move at an absurdly fast speed. So you can't bring that kind of amateur, you know, we're all making a short film together mentality. It'll kill you. Yeah, so you have to become a production, you know, you're a treadmill.

To your earlier question about all the people in the world making YouTube videos and whatnot, you throw 90% of them into a TV production, they'll curl into a ball and they don't want to kill themselves. It's just such a different thing and no one's ever ready for it. I was halfway ready for it because I was at least really experienced in commercial production and I had done a bunch of pilots so I was comfortable in that world. I wasn't literally an idiot off the street who made a weird short. So sometimes that alone prohibits a lot of really talented people from succeeding because...

It's a beast of a thing you're taking on. A TV show is just unlike any other creative endeavor. You know what I mean? Not that it's better or worse or harder or easier. It's just different. When in the world of creativity do you take on that volume of work to crank out and maintain some kind of quality? And how did you do it personally? How did you manage your time and your schedule without killing yourself?

You know, I didn't. It almost killed me. It was the most stressful, busy, chaotic four years of my life. It was really unhealthy. It was damaging. There's no good answer to it. I think most people will tell you the same thing. It was certainly fun while I was doing it, but looking back, it was just a nightmare. It was just like a keep your head down and put blinders on and keep your eye on the end. Surprise, you know? It's like I certainly wasn't well adjusted about the whole thing.

or even got to enjoy it the way I should have. It was like going into war. Yeah, I was just thinking that it is like a war because you're doing this thing that's a mission that has to be completed and it's do or die and you can't give up, you can't stop. And at some level in your mind, like you said, you have to put blinders on and just dig in because you realize, okay, I'm in this and there you go. Yeah. And I should say, going to a real war would definitely be worse and more stressful. Probably. That's your point. Yeah. Less people. It's amazing how many people have the same story to tell. Even people you would think would be so experienced and have it dialed in. It's just like you'd never get it dialed in. It's just always a race. And it's always chaos. It's hard. You can hopefully get a little better at managing it. So do you get a break when you start those 10 episodes and then HBO buys it? Are you that the treadmill has begun and never stops at that point?

How many? It was three seasons on HBO? Yeah, it was three. And the reality is, I wish it was that simple where, oh, here's the break, and then we start again. At least then you can get your head around it. The reality is, when it's going on the air, you're still wrapping the production. When you wrap the production, there's a lull where you have no idea if you're renewed or canceled. So you're completely stressed out, getting ready to pitch new shows because you're waiting for the shoe to drop. And when they do say yes...

you're already too late and you're racing against the clock to catch up. So the in-between stretch is not relaxing in any way. After the second year, the first year, at least, it was good news, even though it was a little low. After the second year, we got canceled. We were off for like six months and then they changed their minds for some reason and we were back on. So that whole stretch was filled with lobbying to resell it somewhere else and, you know, pitching other shows, just being depressed, you know, whatever it is, it's not a relaxing time. Let's back up to the actual debut. How long did you work on episodes before they debuted The Life and Times of Tim on HBO? It was about a solid year. Our production was like a 12-month production. And when they debuted it, are you still in production or had you produced all the shows that they had bought? We might have been wrapping it up, but just barely. Like we're maybe two or three weeks to go as the premiere was going on. So did you get to enjoy any of the...

accolades and any of the glamour of having your own show on HBO? I mean, I would call it glamour. There's no glamour in show business? We had a nice premiere party at the House of Blues, and that was a fun night. I mean, the production itself was always in a divey place in Burbank. And we didn't have, you know, we were a pretty low-profile show for them, so it wasn't like a big Hollywood premiere with a red carpet or anything. I would get invited to the HBO parties. That's the most glamour. You know, they have their Emmy parties and Golden Globe parties. But, yeah, there's no complaints at all. It was one of the most exciting, especially the first season going on the air.

exciting in a way I can't even explain you know when that first show came on that first night I was just like an out of body experience you know I can imagine did you sit and enjoy it and watch it or were you still just in the thick of production yeah no we watched that premiere we actually watched it we had a party at the house of blues and everyone was there all my friends and the staff and the you know agents everyone showed up for that and it was a pretty pretty amazing night and then what was the response from audiences critics etc You know, in the end, great. It was always mixed reviews. It was one of these shows where, and that's the interesting thing. Like, I obviously focus on the good ones, but we were lucky enough to have some of the top critics, like Tim Goodman, who was always very vocal, you know, was the top guy for the Hollywood Reporter at a time, the San Francisco Chronicle. He gave us a rave review, saying it's brilliant, one of the best newcomers to television, this and that. New York Post was the same way. Variety and Hollywood Reporter, you know. We had some great ones. And then there were just as many trashing reviews, you know. So it was like a love-hate kind of show. Some people just aren't ready for this.

slow-paced, unproduced thing. All those people who didn't like the show, I mean, they were just wrong because the show was so fresh and so personal, you know, because your personality just exuded through that show to a point that made it so idiosyncratic. It was unlike anything else. And yet you were able to build on that totally relatable, regular guy persona, these crazy, absurd situations, which made for great contrast. And it was just a very unique show and it just had a very unique feel.

Thank you. Yeah, and that's what I think what I liked was, it's not going to have the biggest audience because it's an acquired taste, but the people that like it love it. And it was a really passionate core fan base that we still have today. You know, that's what they like. They'd rather have a smaller number of people that would die for the show and know every little bit of trivia and diehard fans than have a lot of people in the middle and kind of like it because it's good enough, you know. So I would not trade that for anything. I love it.

You know, the fans of the show are always the best part of it, just getting to hear what they think and what they like. That's great. So then how does the show end after four years of work? Well, they just kind of said we're canceling. You're wrapping up. Was it just based on ratings or what was their rationale? We would have gotten canceled long ago because our numbers were, you know, like a lot of the shows, they have the big hits, they have the medium hits, and they have the ones that are cult favorites. And so we were, we were in the smaller batch. So it wasn't a ratings issue ever. And, you know, it's one of those things you see with a lot of shows. And they said to me, they said, not every show is meant to be on for 10 years. Like we did it. It worked. We're happy. Let's wrap it up. It's like, we don't, we need to clear. They can only put so many shows on each year.

You know, you never know. If there's a real answer, I'd probably never hear it. Nobody's ever going to be honest about that. Yeah, you know, three seasons. How can you complain?

Yeah. So then what does your life look like after having your own TV show? You're back to, you do a little bit of advertising. You're still doing pilots, right? Painting or what is it? I've got to sell another show. It's mostly pilots. I'm lucky we're having that. It opens up doors for sure. And it puts me in a certain regard at the network. So I'm always grateful that I can go in and pitch things and they'll listen. And I've been selling a bunch of them. It's just, you know, you've got to get one on the air. There's a difference between making a pilot and having a show on the air. So I'm just cranking away until it happens again. Awesome. I hope it happens again for you.

Thank you. And thanks so much for talking with me today, Steve. Yeah, this was fun. A lot of fun. If you enjoyed this podcast, go to HowToWriteFunny.com to find more.