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Judd: When things started going really well for you, were you able to enjoy it?

Louis: Oh yeah. I remember the first time I did Letterman. I had all these thoughts reeling in my head that I had to do this or that, and then when I got on, right before I got onstage, I thought, Don’t forget to enjoy this because you’re going to fucking kill yourself if you don’t enjoy this. And I’ve always remembered that. It’s all very fleeting, you know.

Judd: That’s the big thing about it hitting a little later in life. You’re wise enough to realize: Oh, this is a big moment.

Louis: I’ve never had all-at-once successes. I’ve never had any big leaps, the rags-to-riches thing. Everything has been one foot in front of the other, one step at a time. So many times I heard, You’re up for this thing, this is the one, and it’s going to be huge. And it never happens and then it’s back to coming down to earth. You get blue balls from that, you know—like, This is going to be it! And you start thinking about how you’re going to change your life.

Judd: What was the big one of those for you?

Louis: I met with these people at Good Machine, which was an indie film group. They were making some great stuff, and they repped this movie I wrote called Delicious Baby. It was this fucked-up movie about a woman who moves to a small town and everybody worships her and meanwhile she’s been eating all the kids. And, uh, nobody wants to believe it because they love her and a robot ends up choking her to death. So they read it and they took me to lunch. They sat me down and they said, “We have some big news. We’re making Delicious Baby. We have a green light.” And that feeling was incredible. What an amazing feeling. Anyway, we made the movie and it won an Oscar.

Judd: End of story.

Louis: Yeah, no—so it didn’t get made, obviously. And I had to come down from that. Oh, that fucking hurt. That was brutal. There were a few of those kinds of things. I thought I was going to be on The Tonight Show with Carson. I got a call saying I was going to be on Letterman when I was nothing, a club comic. At the time, Frank Gannon booked the Letterman show and he told me he was going to put me on—and then he retired. I was really young then. A shot at Letterman could have totally changed everything.

Judd: In a good way or bad, do you think?

Louis: I’m glad I didn’t get it. I’m glad for every single thing I didn’t get.

Judd: I always felt the reason why I was interested in comedy was that I was on some level hostile and looking for answers. When you look back, what do you think was the fuel for your work?

Louis: I think comedy is a freeing thing. It’s not even an escape. It just feels good. You know what I mean? My parents were divorced around the same time as yours—I was in fifth grade, ten years old. Those were formative years. I was awkward and I couldn’t quite score the way everybody else did. I didn’t feel like I was succeeding as a kid. I was bad academically, always behind, always in trouble. I had friends and stuff, but I didn’t feel like I was winning in school. And comedy was this amazing thing because comedy is like saying the wrong things—when you see a grown-up do it and they succeed at it and get applause…

Judd: When did you tune in to what comedy was?

Louis: My first love was Bill Cosby. My friend Jeff had a whole stack of his records; we would just sit and laugh. I loved the sound of it. I loved the sound of his voice and hearing the audience and the nightclub feeling and how it sometimes felt like a concert. I used to listen to how the record sounded. Oh my God, I just like—it put a real lust in me.

Judd: What’s the thing that Cosby did that you wish you could do?

Louis: I wish I could control myself like he did. I wish that I could…talk…like…this…on…stage. Respect the negative space. Respect the silence, let it alone. I wish I had that kind of control. I came up in the Boston clubs scene where—

Judd: It’s combat. You learn it as combat.

Louis: And I still—whenever I’m watching my opening act on the road or if I’m in a club, I’m like, They’re all gonna leave. They’re not going to be there when I get out there. Like, I need to get on right now. I always closed the show because I was too dirty and too loud. No one wanted to follow me.

Judd: It all changes when the crowd is there to see you. How many years has it been for you where they’re really there to see you in a big way?

Louis: I had done Lucky Louie and it got canceled, and then I did this special called Shameless. It went on the air and I got a call from the guy at HBO: It’s good, it’s good. Anyway, I had built some shows, booked some touring clubs, and one of them was in Philadelphia. I had a week booked there—you know, you do Tuesday through Sunday. You have two on Friday, three on Saturday. Any other week I go and nobody is there on Tuesday. Fifty people Wednesday, a hundred Thursday. Friday and Saturday are packed if the show’s any good. That was for years, you know. For like twenty years I had done things like that. But anyway, I got a call one day. This was in January and I had Philly booked in April, and they say, “We want to add a show on Thursday in Philadelphia.” And I said, “Why? Why the fuck do they want to make me do another show?” And he said, “Because they’re all sold out.”

Judd: Three months in advance.

Louis: And I was like, “What the fuck did you say to me? They want to start adding shows?” It had never happened to me. That’s a big fucking deal. That was a big thing, to suddenly go to clubs that were sold out well in advance—they’re all there to see you, and you’re taking the door, and the club that you’ve been working for and has abused you is suddenly, you know, “sir” and “please” and “thank you.” It’s a weird thing. I started doing theaters in 2007 to 2008, seven hundred and fifty to fifteen hundred seats.

Judd: Does it change your act?

Louis: It’s a huge amount of pressure. ’Cause you have to be really great. When you’re the headliner at some club, you’re just the last guy. You do forty-five to an hour, close strong, and make people feel like they had a complete eat. When you do well as a headliner in a club, people are like, “That guy was good, that guy was good.” But in a theater, there is an enormous amount of pressure because this is their choice for the night. So you want to deliver. And I get anxious about that. Once you’re doing twenty-five hundred seats, five thousand seats—there’s a whole other thing there. It has to be phenomenal.

Judd: And you’re turning the whole act over, too. Carlin would turn it over, but he did it over a few years….

Louis: He did a gradual thing. But for me, it was more interesting to do it this way, to think of each year’s act like a different book that I wrote.

Judd: Are you aware of how much that’s changed comedy? How everyone else is looking at their acts because of you?

Louis: I’m not aware of that. I know that some people don’t like it that I say…Look, when I started doing a yearlong tour and a stand-up special, the next time I would tour, it seemed natural for me to let my audience know it’s a different show. You’re seeing a different show. I never was bragging to other comedians. Some comedians got pissed off because they thought I was bragging. I don’t give a fuck what they think.

Judd: I do feel a sea change from it. It seems to have inspired people to work harder, to evolve who they are on a daily basis. I used to work with Larry Miller at the Improv, and he was incredible, and he had this polished act. He was the one who urged me to write more. To treat it like a job. He’d do his Thanksgiving bit, and it could be one of the best bits of all time, but now I feel—in the best possible way—that comics feel the pressure to be in the moment with what their life is, with their act.