And Here's the Kicker: Conversations with 21 Top Humor Writers on Their Craft

by Mike Sacks

  Also, I came from a sketch background, as did Conan. That's what I saw as a fresh take on the format. If you look at all of the failed talk show hosts who preceded us — Pat Sajak, Dennis Miller, and all the rest — they tried to do the ironic reality-based material. In my mind, no one was going to do that as well as Letterman. So why even try?

  You mentioned the TV critic Tom Shales. Well, he eventually came around to enjoy Late Night quite a bit. But critics never did represent our target audience. The day after the first show aired, we received calls from so many comedy writers — including George Meyer of The Simpsons, who's known to be a high critic of anything that isn't top quality. And he said, “You solved it. You figured out a new way to do a talk show.” George wrote for Letterman's original Late Night show, so for him to say that meant absolutely everything.

  Critics may not have represented your target audience, but, even so, the comments that first year must have stung.

  It wasn't just the critics. Warren Littlefield, the then-president of NBC Entertainment, hated certain elements of the show, including Andy Richter as the co-host.

  Was Littlefield the executive who called Andy a “big fat dildo”?

  No, I don't think so. I think you're getting Andy confused with an actual big, fat dildo. [Laughing] I kid Littlefield.

  But, you know, we didn't really care about the reviews or the critics too much, because we felt — at least I did — that we were on the right track. But it was certainly bumpy at first.

  What's interesting is that eight weeks into the show I got married and went on my honeymoon. And I watched a rerun of the show. There were some great moments — some great bits that I was proud of — but there were also a number of times when there was deathly silence. Conan didn't quite know how to pull himself out of those situations. It made me realize that the power of those moments is so significant. One doesn't see that kind of death on television often. It's very jarring for a viewer — and I could see how it could color a critic's whole perspective.

  You saw it differently watching it on a TV than you did from the studio monitor?

  Yes.

  I wonder how many talk-show writers have even bothered to do just that? You would almost think it would be a necessity. It reminds me of how Elvis would insist on listening to his singles on the same type of record player that his teenage listeners would use.

  I think writers should. You see a show differently than you would otherwise. You see the show with fresh eyes, just as a home-audience viewer would — which is how you really should see it.

  Another thing, too, is that late-night shows are not like sitcoms. They're not sweetened with laughs. They go out in front of a regular audience, and they just live or die. And on our show, we were trying all kinds of stuff. We weren't shy; we were taking a lot of big swings. But there were more homers and strikeouts than singles and walks.

  Wouldn't you rather go for those flashes of brilliance, even if you might earn some uncomfortable moments?

  Yes, absolutely. I view that type of failure as a very positive type. If we hadn't been that bold and tried to stretch, then the show wouldn't have the unique identity that it does. I call it our “flailing period,” and it was a necessity.

  And, by the way, it was thrilling. It was the best job I've ever had, and the one I'm proudest of.

  Let's talk about Triumph the Insult Comic Dog. Why do you think people love him so much? Even Terry Gross, the host of NPR's Fresh Air, is a huge fan — she's had Triumph on the show quite a few times.

  Triumph made her snort on the air. It's funny what makes you proud. I think the reason that Triumph works on everybody's level is because he's protected by his own layer of irony. I mean, the character was born as a completely ironic joke. It was spun off from an old bit that I had done on the show for a number of years, in which we had realistic dog puppets play Westminster show dogs who competed against each other by doing Jack Nicholson impressions or singing “I Will Always Love You,” the theme from the movie The Bodyguard.

  And then on one show — maybe four years into the bit, around 1997 — I suggested we bring out an insult comic. I just thought of the phrase “for me to poop on.” But if you watch that first bit, the joke is 90 percent irony; a dog isn't going to be a good insult comic, because he has a limited repertoire.

  After Triumph very quickly became a hit, I realized that he could provide a kind of cathartic reaction for the audience when Conan had goofy guests on the show — like John Tesh or David Hasselhoff or William Shatner. Here was this ridiculous puppet who could say what everyone else might have been thinking.

  Also, the fact that it's a dog puppet mitigates the meanness and the shtickiness. It reminds you that on some level you're supposed to think this act is ridiculous. And it permits you to laugh at the straight, nastier insult jokes that you might not have laughed at if they were coming from a human. So the character becomes a little more mainstream than, say, a comedian at a roast.

  How many of Triumph's jokes are written as opposed to improvised?

  A few remotes have been mostly improvised — it really depends on the situation — but we generally write jokes in advance, sort of imagining the kinds of people or situations we're going to encounter.

  I always do improv, too, and we usually bring a writer or two with me to help out. When Triumph visited fans in line to see a 2002 screening of Attack of the Clones, one of our writers, Andy Secunda, came up with the best line. I'd seen the first three Star Wars movies, but I didn't know the details too well. One adult fan was dressed as Darth Vader, and I asked Andy, “What's that shit on his chest?” Andy quickly came up with a joke that will probably be the funniest line Triumph ever utters: “Which one of these buttons calls your parents to pick you up?” It's overwhelmingly the line I hear the most.

  Triumph really seems to fluster celebrities and performers, even professional comedians who normally know how to play the role of straight man.

  I always tell people, “Don't try to top Triumph.” That's the first thing. You shouldn't do that, because you're going to look like an asshole. If you're smart, you'll just sort of smile. And if you're even smarter, you'll just laugh, because nobody's expecting you to say anything if you're too busy laughing. You're covered; you're just being a good sport. Once in a blue moon someone reacts in a funny way — a lot of the Star Wars fans were funny because they were natural and reacting honestly. But, usually, we just cut to the next joke.

  We were talking earlier about how Lookwell is a “lost” comedy project that has an underground following. You were the executive producer for another lost project that is now much loved and respected, but was only on the air for only a short amount of time in 1996: The Dana Carvey Show.

  Any show is capable of becoming a lost project. I mean, if the executives had not given Conan a chance, we'd now be talking about Late Night with Conan O'Brien as a lost project. But the problem with The Dana Carvey Show was that it just didn't belong in the 9:30 time slot, which was during prime-time, after Home Improvement. It was a sketch show with a late-night sensibility. We were trying to be the rebels with the sweaters, but following Home Improvement, even the sweaters were too much. We needed to wear Mickey ears.

  In the first episode, Dana Carvey told the audience that the show was for “baby boomers who really want counterculture humor.”

  That's how we felt.

  It looks like they didn't want it.

  Oh, no, they did! There just weren't as many who wanted it as we thought. What I didn't realize was that Home Improvement was a show that parents watched with their kids. I knew Pamela Anderson had been on it, and I just assumed that it was a guys' show. Later, I found out that it had a huge audience among children. If I'd just had the common sense to watch Home Improvement before we went on the air, I probably would have been a little smarter about everything.

  I suppose the very first sketch on the first episode didn't help your cause.

  Right. That was the sketch in which Dana
Carvey played Bill Clinton. In order to prove that he was compassionate — that he was both a father and a mother to the nation — Clinton fed babies, then puppies and kittens from his lactating breasts. Real puppies and kittens.

  We basically killed ourselves then and there. Maybe if we hadn't done that sketch, the audience would have given the show a little bit of a chance, and we might have figured out some sort of compromise that would have made people okay with it.

  Do you think the reaction would have been different for that Clinton sketch if the animals had been puppets, instead of real?

  I just think that so many people found the idea of portraying a sitting president in that way to be disrespectful. Even though it was Clinton, the image was gross and dirty. It had everything going against it.

  We actually had planned to start off with a different sketch, a Nightline parody. But we chose this one because it featured Dana exclusively — well, him and the animals. Louis C.K., who was head writer and producer, said to me, “You know what's great about doing the suckling sketch? It's gonna draw a line in the sand right away. It's gonna tell people that this is the kind of material we're going to do — either you're with us or against us.” For some reason, I agreed with that logic, but I should have known better. We put it on, and we paid the price.

  We received tons and tons of angry phone calls and letters. Taco Bell, who was the sponsor, acted like they didn't know anything about it — they didn't want to get in trouble, and they sort of disowned that sketch. But they knew all along. They had their name attached to that individual episode, “The Taco Bell Dana Carvey Show,” and the executives had seen the taping.

  What's rarely mentioned is that not only did the first episode have the Clinton sketch, but it also had a sketch that featured the character of Pat Buchanan eating the live heart of an illegal immigrant.

  [Laughs] That was much easier to take after the breast-feeding. The heart image was extreme, and probably not ideal for what we were trying to accomplish, but I think we could have gotten away with it. On the other hand, there's just some thing about the combination of a tiny animal and a man's nipples that tends to upset viewers. Isn't that an old comedy saying?

  The writing staff for The Dana Carvey Show was incredible. Besides Steve Carell, Stephen Colbert, Louis C.K., Spike Feresten (who wrote the “Soup Nazi” Seinfeld episode), and Dino Stamatopoulos, who wrote for Mr. Show, you also had Charlie Kaufman, who would soon write the screenplays for Being John Malkovich and Adaptation.

  Charlie kind of got screwed in the end. We hired him to write weird, interesting stuff, but we received a lot of pressure very quickly to try to make the show more acceptable for families. We didn't really have the confidence at that early stage to take a lot of risks with his kind of material. For instance, Charlie wrote a sketch about a guy who owned his own postal service, “Manny's Postal Service.” And he was competing with a neighbor who also owned a postal service. It was very dry, and it only got titters in rehearsal, so we didn't air it. If we had just had a little more success and a little more confidence from the network, we could have aired sketches like that one, because we knew they were funny.

  In doing research for this interview, I read quite a few articles in which you and your humor are described as “intellectual.” Do you think that's an accurate description?

  If I'm an intellectual, I'm a very limited one. I read, but I'm definitely not well-read, as far as fiction or big fat books in general are concerned. I'm not that great a wordsmith, either. Those aren't my strengths. But I think I am intuitive enough to be able to write material I think is smart. A lot of writers I work with were English majors or liberal-arts students, and they received a more well-rounded education than I did. I wasted a lot of time in college, and I didn't go to a very good high school.

  How good of an education does one necessarily need to become a humor writer?

  You mean an academic education? You don't necessarily need one. What's just as important, I suppose, is to be self-educated — to read and soak in as much as you can from the world at large. Del Close [a Chicago teacher of improv comedy] once said, “The more you know about, the more you can joke about.” And he had way funnier heroin material than I've ever had.

  Your work has also been labeled “edgy.” Do you think that's an accurate description?

  For me, that word is clichéd. It's kind of an embarrassing word. I prefer “dangerous.” No, I don't. That was me being “ironic.”

  Do you think journalists feel this way because you juxtapose very adult themes with children's formats, such as animation and puppetry? It's a heady mix.

  Sure, I can see that. This is where the word “edgy” gets embarrassing, simply because there's been a lot of shock comedy in which something cute getting bloody is supposed to be enough. I may have written material that could be viewed as being a little dark or dirty, but I hope the humor goes way beyond those basic juxtapositions. And I don't think my stuff is that angry, either — which a lot of “Edgy 101” comedy seems to be.

  Hopefully, my version of edgy feels more original than that. Obviously, my SNL material gets into subjects and areas the sketches wouldn't be able to get into. Besides the cartoon factor, Lorne once told me that the material that I do on SNL with “TV Funhouse” has a little more leeway because it doesn't reflect the show's sensibility. My material is an independent element within the show. I even created the format to reflect that — I have the animated dog tearing away the Saturday Night Live bumper and Lorne running after it.

  Then again, by doing something like that, SNL is protected, and I'm not. I'm exposed. If the audience likes it, they know it was me who wrote it. On the other hand, if they hate it, they also know that I wrote it. It's my neck and reputation that's on the line.

  Dave Chappelle was visiting the show one week in 2007, and he saw a cartoon I had written called “Torboto.” It was about a robot invented by the military to torture Muslim prisoners, since human soldiers were no longer allowed to torture. It was very dark. And Dave had an “oh, shit” look on his face throughout the whole cartoon. Afterward, he came over and said, “You got balls.” That was impressive coming from Chappelle. Still, I would have preferred, “That was hilarious.”

  It almost sounds as if you think you get too much attention.

  I do think that I get an inordinate and disproportionate amount of attention, truthfully. I've worked with plenty of hilarious writers who have written amazing things that people have never heard of. Sketch writing is generally good money and little attention. When SNL put my name out there with the cartoons, that was a big break. It's made it a lot easier to get other TV and film opportunities, even if I have blown most of them.

  It could have very easily not happened for me. And the evidence I have is that there are a lot of writers and performers I worked with twenty years ago in Chicago who were absolutely brilliant. And yet, as far as I can see, they still haven't had the success I thought they deserved. Some are still waiting tables. When I hear that sort of thing, I'm just stunned. It's a cruel profession where there will probably never be enough work for people who are truly funny.

  Did that sound discouraging? Okay, high note. High note! I feel I did get lucky, but maybe eventually I would've found my way in anyway. If you think you have some talent, just try to find opportunities. Find like-minded people, and keep writing. If you're good and maybe lucky, it'll probably work out. And you won't hate yourself for not trying. Just have something to fall back on.

  Dentistry is a good option.

  Dave Barry

  Between 1983 and 2005, Dave Barry wrote a daily column for The Miami Herald and, by his own admission, never missed a deadline. He also raised two kids — neither of whom, he delights in telling his readers, thinks he's all that funny.

  At its height, Barry's column appeared in five-hundred newspapers across the country — about fifty more than George F. Will's — but back in the late seventies, it took a bit of searching to find it. In the beginning
, his work was confined to The Daily Local News in West Chester, Pennsylvania, and a few other newspapers. This changed in 1982 when The Miami Herald offered Barry a permanent position as a humor columnist. Barry left his job — tutoring business executives in the fine art of writing inter-office memos — and relocated to Miami, a city he once called “the weirdest area of the United States.” For both Barry and his readers this was an astute, welcoming move — most business executives were beyond help, anyway.

  Like all great writers, Barry isn't brimming with self-confidence. He isn't entirely happy with his decisions in life or the current state of the world, which may be a shocking statement coming from a writer who has published thirty books and, in 1988, was awarded a Pulitzer — for having written extensively, and unabashedly, about Neil Diamond songs, the “worldwide epidemic of snakes in toilets,” and the Oscar Meyer Weiner Mobile (that he drove for a week).

  “Humor,” Barry once wrote, “is really closely related to fear and despair.” He believes that comedy originates from a mutual understanding among humans that “we live in an extremely dangerous, scary world, run by all kinds of forces over which we have no control. And we're all gonna get sick and die.”

  Not the lightest quip in the history of humor, and yet not without a heavy dollop of truth.

  Is it true that you never missed a deadline in more than thirty years?

  That is true. I think one of the advantages I had was that I wrote a weekly column, instead of writing one every other day or three times a week. I had time to do other things, such as write books, which made working on the column never quite as oppressive as it could have been. Sometimes I'd get myself into these situations, like writing about the Super Bowl, where I was committed to produce a column every single day. You're totally in the grip of coming up with another idea, and then another idea, and then another, and I cannot imagine living that way.