Was this something of your choosing? I can't imagine any child wanting a janitorial job, especially at their own school.

Another kid, who was a couple of years older, was working as a janitor, and I liked the guy. We were friends. He said, "So, you do this after school, and you get the keys to the school. You get to push that extra-wide broom down the hall, and you get to spray-clean the floor and you use a mop. Then you get to go into the cla.s.srooms. You get the keys to everything."

And what was the appeal of that?

I'd go to the cla.s.srooms and look through the grade books to see what my friends were getting.

Did you ever change any of the grades?

No, no. It was not WarGames. [Laughs] I wasn't going to hack into the system. I don't know why I did that job, truthfully. It was such a bad decision. It was just horrible. It was clear that it was not helping my social standing by doing that.

I did that for about a year. By this point, I was completely obsessed with music and comedy-equally. Eventually, I was able to afford a color TV for my room. I also bought a Betamax tape machine. I'd rent movies and watch and tape all these comedy shows. I would stay up and watch TV later than most kids. I remember watching that first Letterman late-night show [Late Night with David Letterman, February 1, 1982].

Actually, even before that late-night show, I remember watching Letterman's daytime summer show [The David Letterman Show, June to October 1980]. It aired in the morning. I remember discovering that show while flipping through the channels. I saw a birthday cake blow up. That was such a ridiculous image. I remember thinking it was funny in a way that really spoke to me. Here was a guy who was younger than most everyone else on television, and he looked different, and he was sarcastic about everything and everyone else. I think I had that streak in me; this was something I could definitely connect with.

Very funny, very strange. Some bits were almost as scary as they were funny. Like the Chris Elliott characters. Almost frightening.

Were you also a fan of horror?

I loved horror as a kid-I'd watch horror movies and read horror comics-but then there came a point when it only repulsed me. When I realized how rough life actually was, I didn't need to see people getting killed for no reason. I realized that people get killed unfairly all the time anyway. Life is fragile. It was no longer entertainment for me.

But there is a connection between horror and comedy, not to mention other genres. They're all math problems ultimately. When I was writing on Monk, I learned pretty quickly that comedy writers were able to write mystery somewhat easily. It was just like writing a joke: the rhythms of the setup, the misdirection, the payoff. That's what mystery ultimately is. The structure is just 1-2-3. There's a long arc, but then there are shorter elements sprinkled throughout. And then there's the big payoff. Just like comedy.

So comedy writers can write mystery, but can mystery writers write comedy?

No, actually. I think you can jump from comedy into other genres, but not necessarily from other genres into comedy. Or at least not so easily or automatically.

Did you have to teach yourself the elements of mystery?

I did. I just wasn't familiar with that genre. I watched all of the Alfred Hitchc.o.c.k movies and all the episodes of [the 1970s TV mystery series] Columbo. I wanted to see how one doles out suspense and how one sets up a ticking clock. I wanted to see what made a scene suspenseful, how to make a whole story suspenseful. If you're open to doing your homework-and really just embracing it-a comedy background is very helpful.

I suppose comedy is like type-O blood. It's the universal donor.

If you know how to build jokes, you can write any other genre, including mystery and horror.

Where do you think the creative drive in your personality came from?

I'm not sure. n.o.body can get you there. My parents were doing the best they could, but they had gone directly from high school to working jobs. And that's what I came out of. I was the first person in my family to go to college. My parents just did not know how to deal with some kid who at seven or eight years old was writing crazy things, like comic books or scripts to Battlestar Galactica. You know, my parents were working cla.s.s.

I remember high school as being so frustrating. I hated school, just hated it. But anytime there was a chance to do anything creative, I was all over it. I remember one time we had to break off into groups in history cla.s.s and write a Civil Warera story. So I broke off into this group, and I remember we ended up creating this story that was so insane. It was so aggressive and hyperviolent. It ended with a fight between a slave and a slaveowner, in front of a cotton-baling press. The slaveowner falls into it and comes out of the machine in the shape of a cube.

We had to read the story to the cla.s.s, and we were laughing so hard. Everyone else wrote a real story, and we wrote a Bugs Bunny cartoon that ended with someone falling into a cotton-baling press-and coming out as a cube. It was just so out of step with reality. [Laughs] The teacher was horrified. Not that we got in trouble; it was just like, "No. That's not how you do this."

So what did that experience teach you? That you could have fun outside the confines of what teachers and administrators wanted from you?

I didn't even know what it was. I just felt it was this chance to do something. I didn't even know what to do with this feeling, this drive to make something. It was an urge and there was nowhere for it to go. I do not come from a background of performing. n.o.body in my family is really creative. There was n.o.body to say, "Since you are interested in this, you should go do this, or go do that. Or go to this school." There was none of that. I was just dropped in the middle of the ocean, not really sure which way to swim. Or sink.

I was living in New Jersey, thirty miles away from where everything was going down-but it was like another planet. I didn't know how to get from where I was to there. It could have been the moon. I was operating as such a second-cla.s.s citizen, anyway. I felt like I didn't have a place in New York City. I felt like I would always be exposed, that I would hear, "Who in the h.e.l.l do you think you are?" But at some point, the compulsion and the need to create eventually outweighed any of the insecurities that went with it. I felt that I just had to do something. That something was going to happen.

So, while still working at the music store, I started writing and publishing a fanzine in the late eighties called 18 Wheeler. I was about twenty. It was a chance to combine music and comedy. At this time, there were so many awesome music fanzines, and I just wanted to create something similar.

Was there a frustration that you weren't on the inside track? That you weren't writing for the Harvard Lampoon? That you weren't meeting contacts in the professional writing world?

I have to say, I'm still haunted by the fact that I did not go to a good school. I went to a community college in Jersey [Middles.e.x County College]. I worked for ten years in a record store, until I was around twenty-seven or twenty-eight. This haunted me for years. I felt I had f.u.c.ked up. I just didn't have any kind of guidance. I had to kind of stumble my way through all this. I lost my twenties. I really didn't know any other way to do things. But you have to teach yourself the rules. That's the only way to go through it. And I think I'm happier now because of the fact that I went through it alone. If it means I got to where I am now, then that's where I should be. I'm happy with where I am now. I'm in the right mind-set to be doing this. And there's nothing I can do about the past anyway.

I was alone. Totally alone and isolated. But there were some people who were really important to me. There was one guy in New York named Gerard Cosloy; he was a DJ at WFMU for a while. He was also the owner of a record label called Homestead Records, and he later became one of the owners of Matador Records. He had an amazing track record of putting out these fantastic groups-Sonic Youth, Big Dipper, Dinosaur Jr. He also published a music fanzine called Conflict, which had the funniest record reviews ever. Gerard really combined humor and music; he was the gold standard for that. He could be mean with his writing sometimes, but he was always on the right side of things. He was fighting the good fight.

So Gerard was just a huge influence on me doing my own fanzine. This guy was managing to be legitimately funny-as funny as any comedy writer out there-and he also had amazing taste in music. He made a point of pushing the things that people needed to know about to those who might not have known about them otherwise.

I think younger writers might not be aware of how important fanzines were to music or comedy geeks pre-Internet. In many ways, fanzines were the only lifeline.

Yes, absolutely. And they were very accessible, these fanzines. This was the equivalent of the Internet then. You had to piece everything together yourself. You had to reach out to like-minded people, and this was one of the few ways to do that. So from that, I decided to put out my own fanzine.

At some point you either overcome everything and you do your own thing or you don't. You can stay on the one side where you don't ever make things. There are a lot of people who don't create, and that's fine. But there does come a time when you either do it or not. I'm not sure why I did it, truthfully. I'm not sure why anyone does it. But there just comes a time when you have to decide.

Did you ever graduate college?

I did. After I went to community college, I transferred to what later became the College of New Jersey. At the time it was called Trenton State College, but they later changed their name. They didn't want anything to do with the name Trenton. [Laughs] They felt Trenton, New Jersey, wasn't a great selling point. It took a long time for me to graduate. It took me about eight years to get through college.

Did you make any friends?

Not really. I wasn't on campus. I was a commuter. I made one good friend at the community college. Outside of that, I didn't talk to anybody; I just went there. I'd do my time and then get in my car and drive to work. That's what I was doing.

After I graduated, I stayed for a few more years at the music store, and then began to write for basketball magazines. I was a huge fan of basketball. There was a magazine called SLAM that was published for kids. It had a hip-hop element to it and celebrated the NBA players. It was not inst.i.tutionalized the way Sports Ill.u.s.trated was. I wrote to SLAM and kept asking them, "Please let me write anything for you guys." And they let me. First small pieces, and then eventually a cover story.

Around 1997, they sent me to a reading event in Orlando, Florida. Some players from the Boston Celtics were going to read to kids in the Dr. Seuss section of Universal Studios. I got a plane ticket, flew from Newark to Orlando. At this point, the Celtics were in the ninth overall spot; they had to win that night if they were going to make the playoffs. When I arrived at the Orlando Arena, I heard their coach, Rick Pitino, screaming as loudly as he could. I could easily hear it through the walls. Screaming and screaming. Then these two players walked out-Antoine Walker and Paul Pierce-after having been screamed at for twenty minutes, and they got into a limo with me. They're off to read to the kids. And they're in the worst mood ever.

They start to complain to the NBA rep who was with us: "Why aren't we ever on the cover of anything? You guys promote this guy, you guys promote that guy, you don't ever promote us!" And now they're yelling at her, and I'm just this big dummy sitting there. Sweat is pouring down my face and down onto my little recorder. The NBA rep starts yelling back at them: "You know why you're not on the cover! We . . . we put who wins on the cover! Winners! That's why!" And then there's quiet and she announces, "So, Tom is going to ask you a few questions about reading." I mumbled something like, "So, ummmm, what kind of books do you like to read?"

I remember one of them said he liked books about money. The other said he preferred books by John Grisham.

I felt like garbage, and I felt as if these two were giving me nothing for this thing. And I wanted to say that being there was beneath me, but that's the part that truly sucks. I felt that I deserved better, but, no, this was exactly what I deserved! It was terrible-just awful. But I had zero experience. It was exactly what I deserved.

I'd imagine that this type of experience could have only helped later with your comedy. You didn't directly go from an Ivy League to a writing room in Hollywood, which would have been limiting.

Everything has worked to my benefit, even the things that felt, at the time, like they were working against me. A problem never comes without a gift in its hand. You may not even be aware of it until five years later. Everything I've done in my life has allowed me to have this wealth of real-life experience. And that can only help.

And, actually, I'm grateful that I did not have the Internet back then. All of the missteps I made when I was first starting out would have been made public. For years, I could fail in private. By the time I got my act together, the worldwide distribution method clicked into place. Private failure is not really a luxury these days.

How else do you think real-world experience helped with your comedy?

There's so much comedy that just deals with show business. Jokes about other jokes. References to references. There are so many writers who write movies about other screenwriters. The pitch is something like, "This story is about a screenwriter who has writer's block, so then he goes . . ." Well, you've already lost sight of the real world. Writing about s...o...b..z is such a cheap trick. Everybody wants to see behind the curtain, but there's such a low ceiling for it. It contains no dynamics from real-life experience.

I can't imagine anyone growing up wanting to write a screenplay about a screenplay. People end up there because their worldview has shrunk to include n.o.body but other screenwriters. I see the same with TV writers, too. They'll know every episode of The Simpsons, but what do they know about working s.h.i.tty jobs? Or, if they do know about s.h.i.tty jobs, it tends to be the bad jobs that fictional characters have worked, like Fred Flintstone working at the stone quarry, or Apu from The Simpsons working at the Kwik-E-Mart.

I don't say all of this from a place where I'm mad at anyone who took that path. I'm just very glad that I have had at least some experience with the real world.

How did you pick radio as your medium of choice?

The appeal of radio to me was simply that I was allowed to do it. Jon [Wurster] and I wanted to do a radio show similar to [the 1970s and '80s TV sketch comedy show] SCTV. We wanted to create a large world. We wanted to create characters. Backstories. Plot lines. An entire, very real world. And radio allowed us to do that. We were using the only medium we had at our disposal. We couldn't work in movies or in TV; radio was accessible.

It really worked to our advantage. The most amazing thing about radio is that it allows for long-form comedy. What other medium even comes close? If we were on television, people would stop watching after three minutes. Movies are out of the question.

Radio allows us to really stretch out. We can create bits as long as we want because people will never say, "This is too long." I mean, some people will say that. If you listen to Z-100's Morning Zoo, you'll hear character bits, but they only have ninety seconds to do it. It's joke, setup, joke, setup, joke, setup. But we have the real estate to create something larger, more nuanced. There's no rush on it. We can take the scenic route.

Another positive aspect of radio is that it creates a very personal connection between listeners and performers.

The amount of time you spend with people who listen to the radio is incredible. If you're a Bill Murray fan, you might spend four hours a year with him. If you're a fan of a sitcom, you spend twenty-two half-hours with those characters. But with radio, you're talking about spending hundreds of hours with a person over the course of a year.

Radio is such a pa.s.sive medium. Listeners are usually doing something else while they listen, like washing the dishes or driving a car or going on a walk. That's a strength, not a weakness. The bond, I think, becomes so much deeper than it would be for other mediums because of that.

It took awhile for an audience to find your show, didn't it?

It did take a while for the show to find an audience, but you can never try to be a version of what everybody else is doing. Even if it seems like the kind of thing that other people might not laugh at, you have to stick with it. Everybody that you admire has come from that same place.

[The comedians] Tim and Eric had a hard time at first, but they stuck with it. Their [Adult Swim] TV show [Tim and Eric Awesome Show, Great Job!] wasn't crowd-pleasing-at all. They weren't attempting to win a huge audience. But they stuck with it, they eventually found their audience, and it's what they needed to do. You have to trust what you're doing. There's something running through everybody that others will eventually respond to.

When you started The Best Show-which really kicked into gear around 2000-was anyone else even doing long-form radio comedy? Jean Shepherd, Bob & Ray, Firesign Theater-all had been long off the air by then.

I'm the only one that I'm aware of. We're still the only one. The first comedy bit we did was in 1997. I then took a few years off to try and find a writing job. I returned in 2000, and the show became just as much about comedy as it was about music.

Do you remember your first scripted comedy radio bit?

I do. And it was more effective than it might have been, I think, because no listener could have predicted it coming. Jon phoned in to the show as a character and we did a routine that we later called "Rock, Rot & Rule."

In 1997, the tape of "Rock, Rot & Rule" became infamous. It was bootlegged and pa.s.sed around as ca.s.sette tapes, particularly among comedy writers and musicians.

Thankfully, I was taping it. At that point, if you didn't tape a show onto a ca.s.sette, you didn't have it. This was before the show was taped and later broadcast on the Internet. So I taped it, edited it down to forty-seven minutes, and handed out ca.s.settes. We got validation from our friends that this was funny. I remember Amy Poehler loved it. There was even a reference on Amy Sedaris's TV show, Strangers with Candy, which took place in a high school with blackboards in each cla.s.sroom. In one episode, someone wrote "Somebody rocks, somebody rules" across one of the blackboards. The funny thing is that when we did that first bit, we were so anonymous. What pedigree did I have? Zero. I was just a guy going to watch live comedy shows every week in the city. And Jon lived in Chapel Hill, North Carolina, and was working as the drummer for the group Superchunk. So zero. Zero pedigree.

What type of pedigree do you really need for comedy, though? And wouldn't that work to your advantage anyway? I mean, no one had any indication that this character you created was a fake.

That did work to our advantage, actually. A lot of people at first thought that [comedian] David Cross was behind it. We also had a lot of people who thought it was a crank phone call. I'd read on sites, "Listen to this guy crank this dumb radio host!" Which, to me, is the greatest compliment ever, because I co-wrote the thing.

It was a great parody of pompous music critics and their ridiculous, wrong-headed theories.

[Laughs] The phones really lit up. I mean, the callers had absolutely no idea that Jon was playing this character-and they were just burning, burning mad. Furious!

Jon told the audience that he felt that David Bowie and Neil Young were "rot" because they had made too many changes to their sound over the years. And yet, he hadn't heard any songs by Neil Young from before 1989. Jon also said that the Beatles fell under the "rock" category and not the "rule" category, because they had so many "bad songs," including "Strawberry Fields Forever." Puff Daddy, on the other hand, "ruled."

I remember first coming up with this idea after reading an article about Texas cattlemen taking Oprah Winfrey to court over a show she did about mad cow disease. They said she had portrayed the meat industry in a negative light, and they tried to sue her, but the case was thrown out. Afterward, Oprah said, "Free speech not only lives, it rocks!" Jon and I were laughing about that, and we thought, What if we apply that to music? We wrote out the script, and I showed it to my wife. She said, "You're going to do this for how long on the radio?" But that night when I came home after the show, she said, "Nope. You were right. That was awesome." It ran for about fifty minutes. And that goes back to what I was saying earlier about long-form comedy. What else can run that long, except for a movie?

You've worked with a lot of great comedians and performers, some of the best in the business. How does Jon compare?

Jon is literally the funniest person I've ever met or seen. He's so quick and is able to make everything go down so effortlessly. But I know how much effort is going into it. That impresses me even more because I know how much he's working to just make these calls sound like conversations.

To make it all seem breezy and real and to be able to play the emotions and know when to start to get mad or sad-just to have the perfect gauge-is extremely difficult. He's got so much range, and he's got so much control over that range. He can very smoothly not draw attention to the fact that we're trying to transition from one beat to another; you don't even notice he's doing it. Amazing.

He has no comedic training, right? No acting background?

No, no, he's just a natural talent who has taught himself over the years. He has "it." I can't think of one thing Jon hasn't been great at. He's been at such a high level for so long, whether it's comedy or music. To have two things that you're great at is shocking. Inconceivable.

Over the years, we've performed hundreds of bits. And a ton of characters. And I still receive plenty of calls from people who believe that the characters Jon performs week after week are actual people.

How do these radio scripts take shape?

We spend a lot of time writing these scripts. The scripts are usually 90 percent written, and 10 percent improvised. Jon and I talk by phone or e-mail and come up with some ideas. "Hey, I have an idea about a guy who does this." Or "What about a guy who does that?" We'll start laughing about a situation, and then we flesh out the idea. Most of these are very tightly scripted. It comes down to, "This is how this needs to be said at this point in the call for the joke to pay off or to set up the joke or to make sure that it all comes together." We'll also make notes for what not to say. Jon will tell me, "Don't ask me this question because that will tip off a joke too soon."

I was going through some of the characters you've created for your fictional town of Newbridge, New Jersey, and I stopped counting at one hundred. The mythology for this town and its characters is so rich and dense. Newbridge has become almost the comedy equivalent of Middle Earth.

[Laughs] Actually, there are more than two hundred characters. The world is very specific. I can't even keep up with these characters. I have to ask a guy who keeps track of all of this. He's almost like the show's historian. We have characters who are distant relatives of characters we created years ago. We have sons, daughters, parents, grandparents, cousins, nieces, nephews. But I love that. That's creating reality from out of nothing. And once you do that-once this world begins to take shape-the comedy becomes stronger for it.

To me, the things I love the most are these comedy worlds, whether it's Melonville [where SCTV took place] or the world that Steve Coogan created for [the BBC situation comedy] I'm Alan Partridge, or the Springfield that was created for The Simpsons-it's all just so full and wonderful. Characters become more realistic, fully fleshed, instead of just being one-dimensional.

A good example of one of your fully-fleshed characters is Barry Dworkin, who has appeared on the show multiple times over the years. In one bit that originally aired in 2002, Barry-as played by Jon-calls the show to seek musicians for a band he's starting called The Gas Station Dogs. His requests are incredibly detailed. The keyboardist has to be an "albino who wears vintage late-sixties NASA-approved s.p.a.ce suits," and his nickname will have to be "Commander Giggles."

That's a good example of a character who is totally delusional. And narcissistic. Barry is forty-four and his only musical experience is once playing in a Rolling Stones and Who tribute band called Tattoo Who. He's four feet eleven inches tall. He has reddish-gray hair that's balding, and a handlebar mustache. He has a purple birthmark on the top of his head the size of a softball. And his dream is to form a group consisting of only very young and extremely handsome musicians, and to record a song that he's spent nineteen years writing called "Rock 'n' Roll Dreams'll Come Through." The song is pure s.h.i.t. There are about fifty characters in the lyrics, all with similar-sounding names ["Rodge," "Roddy," "Denny," "Don," "Betty," "Kenny," etc.]. And yet this guy's ego is through the roof. He's looking at everyone else under a microscope but has no quality control for himself. He's just holding everyone else to some insane standard.

It's sad. It's one of those situations when you know someone is doomed to fail, and everybody can see it but them. I'm obsessed with that.

These characters that you create tend to be a bit clueless about their lot in life. A total lack of awareness.

Jon has talked about this before, but a major influence for both of us was a scene from the [1988] doc.u.mentary The Decline of Western Civilization Part II: The Metal Years. It was directed by Penelope Spheeris, who later directed Wayne's World. In the middle of the movie Penelope asks a series of horrible LA heavy metal musicians where they'll be in ten years. Every single one says, "I'm gonna make it!" Spheeris asks, "Well, how about if you don't?" And they always answer, "Oh, but we will." None made it. Total delusion.

At the same time, I always admire anyone who even attempts to do something different. To accomplish anything is never easy. The easiest thing in the world is to not make stuff. The easiest thing in the world is to choose to not put your neck out there on the chopping block. That is the safest route you can take.

Even if someone makes something terrible-like the music the Insane Clown Posse makes-at least they're doing something that speaks to them. And they kept going even though people told them it was terrible. And they found their audience, and now they built a community around their work. Look, you couldn't pay me to listen to their music, but I still feel like I have more in common with the Insane Clown Posse than I do with someone who just sits on the sidelines and s.h.i.ts on other people's work and who never puts themselves on the line.

But when meanness comes into the equation . . . when a terrible ego comes into play, then that's something that's always bothered me. Have you ever seen the [2003] doc.u.mentary Overnight? It's about a totally delusional, mediocre egomaniac-a writer and director in Hollywood-named Troy Duffy. I'm fascinated by guys like that. Guys like that are the patron saints of everything we do. Duffy is the type of idiot who thinks he's a genius; there's no doubt in his mind that he's brilliant. And it takes no time for him to start rubbing this fact in everyone's face. When you see someone act like that, it becomes clear that the real geniuses-the ones behind the scenes, the ones who quietly do all the work with little fuss-are not out there mouthing off and making people feel bad about themselves. They just do the work.

On your radio show, you have complete freedom to write whatever you want. I imagine you didn't have that complete freedom when you were working as a writer on Monk.

Actually, my writing job on Monk was the best position for me to be in. I had one voice among 150 voices on Monk. We were all trying to build a TV show and to make that show as good as it could possibly be. I also had something that was completely my own at the same time-my radio show. But I think you have to learn how to play with adults. It's a very valuable experience. You need to go through that experience of working with others. If you don't, it's going to be very hard to suddenly be in charge of your own show down the road.

Look at David Chase, who created The Sopranos. He worked for years as a writer on Rockford Files. Look at Mitch Hurwitz, who created Arrested Development. He worked for years as a writer on The Golden Girls. You have to learn how to play nice with others.

So, no, I didn't have complete freedom on Monk, but I did learn a lot of valuable lessons.

TV and movies are such collaborative mediums. You have to be ready to not have everything go your way-even if you're in the top position. There were so many times on Monk that [writer and producer] Andy Breckman, who created the show and was the showrunner, would face actors who didn't love a certain piece of writing. The actors wanted to change scenes. Now, Andy could have just stomped and screamed and made the actors do it his way, but he didn't. It's a give-and-take. So being a part of that and learning that dynamic is a very important tool that you need in your toolbox.

But when you do achieve the freedom to create what you want, it's important to appreciate what you have. I never take The Best Show and the freedom that comes with it for granted.

When you're in a radio studio performing these comedic bits, you're operating in a vacuum of sorts. It's just you, alone with your producer, in a studio. How do you even know when any of the humor is working-or not working?

That comes from just trusting yourself. Basically, I'm talking to myself. You just have to trust that the humor is bearing fruit. It does feel, at times, like I'm on this s.p.a.ce walk. There's nothing to grab on to. It feels that if the cable ever breaks, I'll just be lost in s.p.a.ce and I will die.

But it's helpful when it comes to writing. If I'm writing something by myself, I don't worry that it's not funny enough, because I have the confidence of working in silence. I don't need everyone to be rolling on the floor because I know-or, at least, I hope-that the end result will be funny. That's very valuable when it comes to writing. It's the opposite of being a stand-up.

I'd think that would be another advantage of long-form radio comedy. Silences are accepted. Not every moment has to be filled with laughs.