Poking a Dead Frog: Conversations with Today's Top Comedy Writers (35 page)

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 [Middlesex 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 fucked 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 institutionalized the way
Sports Illustrated
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 showbiz 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 nobody 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 shitty jobs? Or, if they do know about shitty 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 passive 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 passed around as cassette tapes, particularly among comedy writers and musicians.

Thankfully, I was taping it. At that point, if you didn’t tape a show onto a cassette, 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 cassettes. 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 classroom. 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?