In 1990 Bob Odenkirk briefly joined the Second City in Chicago, where he appeared in a critically lauded sketch revue called Flag Smoking Permitted in Lobby Only or Censorama. For his friend and castmate Chris Farley, he created the character Matt Foley, a motivational speaker who scared teens with a warning about his own disastrous situation: "Thirty-five years old, thrice divorced, and living in a van down by the river!"

When Farley was hired by Saturday Night Live that same year, he took Foley with him, who became one of his—and the show's—most recognized and popular recurring characters.

Odenkirk's career has been filled with successes and failures, obscurity and slight notoriety. After working as a writer at SNL, he joined the writing staffs of such short-lived shows as Chris Elliott's Fox sitcom Get a Life in 1991, and the critically beloved The Ben Stiller Show for its only season, also on Fox, in 1992. He briefly wrote for Late Night With Conan O'Brien in 1993, but left to join forces with David Cross (another Ben Stiller Show writer) to create, in 1995, Mr. Show for HBO.

With skits about Satanism, cock rings, and mentally challenged parents—all loosely connected by a narrative thematic thread—Mr. Show was consistently more intelligent and irreverent than anything else on television. But despite critical raves, Odenkirk and Cross's style of humor failed to attract a mainstream audience, and, in 1998, HBO axed it after four seasons.

Since then, Odenkirk has remained mostly behind the scenes. He's written for animated sketch shows, such as Tim and Eric's Tom Goes to the Mayor; nonanimated shows like Tim and Eric Awesome Show, Great Job!; and webcasts like Derek and Simon: The Show. He's also directed films both independent (Melvin Goes to Dinner, 2003) and studio funded (Let's Go to Prison, 2006).

How early did your interest in comedy begin?

Very early. I got into comedy when I was a little kid. I would goof around with my brothers and sisters at the dinner table. My brother Bill and I would imitate the people we met in the course of a day, while the rest of my family ate dinner and laughed. Bill now writes for The Simpsons. Then, in junior high, I would write and perform sketches for school projects. I would do these sketches in various classrooms, and not just in my classes—the school would let me go around and do them in other rooms too.

So, that's really where it all started, but I never thought about writing and performing comedy for a living until I went to college, at Marquette University and then at Southern Illinois University. I wrote radio shows at both schools for three years—live performances and sketches every week. My friends and I performed them in the studio with no audience.

But it was a really long and slow process for me to ever think that I could do this sort of thing for a living. I just didn't know anything at all about show business, or how one gets a job in it. It wasn't a legitimate field. There was nothing real about it.

Who were your comedy influences?

My strongest influence was Monty Python. After that comes the Credibility Gap and Bob & Ray. Also, SCTV and Steve Martin's first album, Let's Get Small [1977]. I loved Python. People always tell me that they can see Mr. Show being similar to Python. In particular, with the way the sketches flowed into each other. But to me the primary attribute of Python was that it had something on its mind and, at the same time, was laugh-out-loud funny. Python actually made you laugh. It wasn't just intellectually funny or clever.

How difficult was it to create the Python-esque segues for Mr. Show, in which each sketch would be seamlessly linked to the next?

I think that's one aspect of the show that's overrated. I'm glad we did it that way. It made all of the shows hang together. Sometimes it was a very clever trick. But sometimes those segues were not very clever. Our rule was that transitions had to work on their own merit, but they also had to somehow comment on the next sketch. That was very hard to do, and we just couldn't do it all the time. When we were really stuck for a transition, we would do something simple, like pan to a poster with a few words that summarized the next sketch—and then we just panned back.

One of the things we experimented with in the second season was abandoning this idea of thematically tying together the show.

Why would you abandon that idea? Wasn't that one of the aspects that made Mr. Show unique?

It became too difficult to pull off. We thought that it would be a neat thing to do, and it turned out to be a drag. And besides, we soon learned that the best Mr. Show episodes were the ones that contained scenes that were vastly different in subject matter and comic sensibility. One scene might be physically comic, and the next more verbal. It was really fun to jump between things that were as different as they could be in presentation and also in subject matter. In the end, you didn't really need to have those strict segues between sketches.

What would you look for in a sketch idea? Did a sketch have to meet certain criteria with the writers?

We would ask ourselves about every sketch, "Is it funny? Really, truly funny? Or do we just think it's funny because we really want it to be funny?" That doesn't sound very scientific, but I think there's an important truth there. We took this very seriously. It was very, very important to us.

Second: What is this sketch about? That was a little challenging sometimes, because we'd have an idea that seemed funny, but the sketch didn't really have anything to say.

Does every sketch need to say something?

No, but it's nice to know the underlying meaning. If you have a sketch that's a bunch of taglines that are stupid and funny, that can just be a list of funny jokes. But if you can think of a unifying point of view for them—something you are clearly commenting on while you're listing a bunch of funny taglines—that's even better.

You've said that quite a few of the sketches from Mr. Show sprang from real-life experiences, including the sketch in which you parodied the Mr. Ed television show. In that particular sketch, you played a talking junkie who "spoke" just like Mr. Ed.

Yes, the "Talking Junkie" sketch. I had a meeting about writing a movie script for Francis the Talking Mule, which was a really dumb idea. I thought, What did the executives see in my past work that made them think I'm the perfect guy to write this? It then made me think about talking mules and what's at the core of that type of comedy. People are just fascinated by something that talks that shouldn't be talking. The notion occurred to me that junkies are just so weird; almost like a different species.

You have a reputation for being a perfectionist. Are there any Mr. Show sketches you're still not happy with?

One was called "Clumsy Waiter." It was from season four, and it was about a waiter, played by me, who spills food on a patron's suit. The maitre d', played by David, insists on paying for the restaurant's mistake, but only for half the cost of the cleaning. It almost devolved into vaudeville, which is what it felt like when we were rehearsing it. It didn't work, but it could have been a good one.

What do you think that sketch needed?

It needed exactly what I pitched and what no one would do. Dino Stamatopoulos, one of the writers, told me, not long ago, "We should have done what you wanted, and I wish I would have backed you on it." What the sketch needed was a little stopwatch in the lower-right-hand corner of the screen with "Time till end of sketch" and a countdown. . . .

How did the writers' room work at Mr. Show?

Very few ideas were not accepted by all the writers by the time a sketch got on the air. You would have to prove it to the group, and certainly to David and me. We both had to like everything.

I'd come from Saturday Night Live, and a lot of what I did at Mr. Show was a direct response to things I thought were done poorly at SNL.

Like what?

Like very little interaction and very little guidance for the first two days of the week before the show—and then all of the material is suddenly brought to a rewrite meeting in the last 14 hours. By that time, everyone's wiped out. Another thing I was reacting to was the way in which ideas were abandoned after one reading at SNL. If the ideas didn't go over well at the first pitch meeting—for whatever reason—they were thrown away, even if they were good ideas.

There would be a reading of a sketch in front of everyone, and it didn't go over well, and then that was the end of that. And I thought, Well, why get rid of it so quickly? If you had done a rewrite, you could have ended up with a good sketch.

To me, the best sketch comedy, like Python, is not about recurring characters and situations but something different and fresh. And viewers might have a lot less patience for that than they would with the tried and true—with the familiar.

Why do you think that is?

I think people are looking at entertainment not for ideas; they are looking at it for an easy kind of distraction. And I think this especially holds true as viewers get older—when there's less patience for being challenged. They reach a point where they don't want to look at a show and have to ask themselves every two minutes, Where are we now? That's exactly why high school kids and college kids, whose brains are orgasming with ideas, are thrilled by sketch comedy.

If you go to colleges and see how many goddamned sketch troupes there are, it's insane. It's like, Calm down! There are sketch festivals in which 50 groups are going to perform in three days. What the hell is going on? There can't be that many people who want to do this. But that's where you are headed at that age. Then people get older, and they just don't want to hear a new idea. They want to sit back and watch the same people do the same thing they did last week. That's what TV exists for—it exists to be a mild sedative.

Like Mr. Show, the Pythons didn't necessarily get the credit, or the ratings, they deserved at the time.

Yeah, that's true. I saw the guys from Python when they reunited to receive an award years ago, and John Cleese got up and said that he wished Python had received the award back when they really needed it. And now I think about how hard it's been for David and me to get a Mr. Show sketch-movie made, and how we really had no control in the making of Run Ronnie Run!, a film we both really think is subpar. And it occurred to me that Python had a benefactor—George Harrison.

If you're going to create a comedy like Python or Mr. Show, you need a benefactor. No one's going to take a chance on that type of comedy otherwise. If Python hadn't had George Harrison, they never would have made any movies. It's not like a studio wanted to make a movie with them.

One of the things you seemed to avoid with Mr. Show was using topical material. The material has remained very fresh.

That was another thing from Python. We would also try to avoid repeating characters. Python had two or three characters that came back a few times, but that was about it. When I left SNL, I really wanted to get past that sort of thing.

Mr. Show also refrained from using too many catchphrases. SNL is notorious for doing just the opposite. But you did write a sketch on SNL that featured a line that became a catchphrase of sorts: the "van down by the river" line, in Chris Farley's motivational-speaker sketch.

It may also be one of the strangest sketches I ever wrote, because it's not really funny. It has a catchphrase, but it's different. That character is telling a story with that catchphrase. It paints a picture; the phrase has a lot more meaning to it than just a catchphrase that stands alone. That particular sketch contains a very strong idea: that this guy uses his own tragic career path as fodder for his motivational speaker bit. But there is a lot more to it when Chris did it, and he made that character whole. It's not a gimmick. You felt like there was a real person in that character.

That character became a lot more cartoonish after you left. The writers seemed to replace the sadness with easy laughs.

I told Chris and the writers, "Look. Whatever you do, the one thing to remember is: don't start from the ending. Start from the beginning, so that you have somewhere to go." Almost every time Chris did that sketch after I left SNL, he started by breaking the table.

You've said in the past that Robert Smigel helped you become a better sketch writer at SNL.

I don't understand where Robert got his instinct for sketch comedy. I had written many sketches before I got to SNL, but he taught me a lot. He used to talk about finding the core joke of your sketch, which was something that struck me as a great lesson and one of the first things that a writer should think about when it comes to sketch comedy.

A sketch starts off as an idea, or a point of view. You then take it and you twist it and play with it and try to find an ending for it. Robert just had a sense of what the core idea for a joke should be—what mattered in a sketch and how to construct the sketch around what matters. He was very aware. He wrote a lot of sketches that were definitive for our time, for our generation. For instance, the Star Trek sketch from 1986 in which William Shatner tells the Trekkies to "get a life."

Robert wrote a lot of amazing sketches. "Da Bears" was his idea. Just so many things. I've said in the past that he saved that show, and I really think he did. He gave that show, I think, the strongest and smartest sketches that it had for a couple of years. When Robert arrived, stand-up comedy was really at its peak, and sketch comedy was not happening. SNL was kind of a mess. But he definitely helped change that. v