Surrealist comedian Steven Wright has been deadpanning jokes his entire adult life. Thanks to a mix of originality and opportunity, he managed to springboard a triumphant Tonight Show debut into a four-decade career that continues to warrant a heavy stand-up schedule. He spoke with Las Vegas Magazine’s Matt Kelemen in advance of his Nov. 25-26 appearances at The Orleans, reminiscing about crucial points in his career and the influences that shaped his iconoclastic style.

I just happened to start watching Reservoir Dogs a half-hour before getting the offer to interview you. I remember being in the theater having no expectation of what I was about to see, and the first thing that happens after the opening scene is your voiceover. That’s permanent. People are always going to come back and watch it and they’ll hear your voice forever.

I know. I was really lucky to get in there. A guy I just talked to told me it’s 25 years old now, that movie.

Yeah, and I just found out you got with Reservoir Dogs because of somebody you worked with on your own Academy Award-winning short film, right?

My friend—well, I didn’t know him at the time—Dean Apricot directed it, my film The Appointments of Dennis Jennings, and his wife (Sally Menken) was an editor on the film. She edited Dennis Jennings, then she went on to edit Reservoir Dogs, which was Quentin Tarantino’s first movie, as you know. She edited all his movies, though she tragically passed away several years ago. The reason I was in there was because they didn’t even have the person on the radio. It was almost finished, and she suggested me to him. That’s how I got in there.

I see a parallel with your Tonight Show experience. You didn’t see either one coming, or what they would mean to your career later.

Yeah, definitely. As far as that first Tonight Show, I wanted to go on there since I was 16. That was my dream. That was my fantasy, to be a comedian and go on there. And I went on when I was 26, and that six minutes changed my whole life. So Johnny Carson changed my life twice. The fact from watching it that I even wanted to be a comedian—that’s how it got into my head—and then when I went on and everything changed.

Have you watched the old Carson shows since they started airing back-to-back...? Carson (as host of The Tonight Show) to me had four distinct eras, and we never see the first black-and-white one. Then there’s this early ’70s period, then a late ’70s, then an ’80s period. I figured they’d really take you back.

Yeah, I’ve seen those shows ... and I can tell by the background, by the set, by what’s behind him, the color of the curtain. I mean the curtain when he came out was always the colored curtain, but the other curtain the performers came in front of would change over the decades. I started watching in ’71 or ’72 or something like that, and, yeah, I can see some of those pieces of those shows and it takes me back to being in my living room in Massachusetts where I grew up. The only reason I started watching it was because my older brother liked to watch it, and since he was older than me we had to watch what he wanted to watch because he was in charge of the television. Everyone else would be asleep and me and him would be up, and I watched it because he watched it. Then I started to really love it. What I like to do is, I like to watch Don Rickles on there. If you Google it, you can see it on YouTube. There you can see the eras change, too, the clothes and everything. That show was incredible.

It’s cool to watch for clues to the time period. You can see something that was just completely different, like a hairstyle or the width of a tie, like what Johnny would wear.

Yeah, yeah, yeah. Lapels and stuff, or a jacket.

The New York Times wrote, “no single career better demonstrates Carson’s now fabled star-making powers” than your debut on the show. Is it true that you weren’t aware of the significance of being called over by Carson after your set?

When did The New York Times say that? Was it a long time ago?

It was either a 2008 article or 2014. I think it was 2014.

Well, I knew. Like I said, I started watching the show when I was 16, so I knew how rare it was for someone to go sit down. I knew that that was unbelievable. I didn’t know it was gonna happen, but I knew that it was pretty freaky. I was a fan of the show. I mean, I knew so much about the show. I was addicted to the show.

What was it like after that sank in? I mean, you knew what it meant for your career.

Look, that was in August. My girlfriend rented a little tiny cottage on Cape Cod, Massachusetts. We rented it for the end of August, you know, we rented it many months in advance. So then I’m going back to Boston doing comedy, and Peter Lassally from The Tonight Show sees me in a club in Boston because he comes to Boston because his kids are going to go to college and he looks at colleges in the summer of ’82. And he comes to Boston and New York, and he sees me in this club. Then I go on The Tonight Show, I go on and I sit down the first time, and then I go on the next … I went on Friday, and then I go on next Thursday. I went on again. I didn’t sit down the second time. It was the only time I didn’t sit down. And then I went back to Massachusetts, and me and my girlfriend went to that little cottage in Cape Cod. It just happened to line up. It was like three days after the second time I was on The Tonight Show, I’m in this little cottage down near the beach—well, it wasn’t right on the beach—but talk about surrealism. All that happened … it was like a movie.

In an interview you called your discovery by The Tonight Show co-producer Peter Lassally “like getting in a cab by accident with Jesus.”

I did? That’s funny (laughs).

What led to you becoming a regular guest on The Late Late Show with Craig Ferguson?

Peter went on to produce Letterman in New York, and then he didn’t want to live in New York any more, so he went back to California and he continued to produce the Tom Snyder show, then he produced the guy that came before Craig Ferguson (Craig Kilborn), then he was producing Craig Ferguson, so he had me on there all the time because I was friends with him since the time I met him. So I was on there all the time until that show ended, and then Peter retired. Peter changed my life by putting me on The Tonight Show.

Did you and Craig Ferguson hit it off immediately or did that evolve?

No, I hit it off with him because he’s a comedian also, and when I first started going on there, some of it was we knew what we were going to talk about ahead of time, but after three or four times it was just all made up. I never did improv like that before. He was so fast and funny the whole thing was like eight minutes of insanity. It was one of the funnest things I ever did on television … just riffing with him.

I interviewed him once. He’s severely underrated.

He is! He has one of the fastest comedy minds I’ve ever seen. I mean, he would make the monologue up. He was incredible. His brain was so fast and so funny, and I would make stuff up and if what I said didn’t work, it didn’t matter, because he would say something and the audience would laugh anyway.

So for someone like you that’s very impressive because you are very aware of the role of the subconscious in comedy, and free-associating. You seemed like a yin and yang: he’s the fast improv guy and you’re the surreal conceptualist guy, and you just fit together well. Have you talked about working together again in the future?

No, I haven’t talked about doing that with him, but we were like a bizarre comedy team after going on there for so many years. To me it was like two guys that were in an insane asylum, and we were in a waiting room. The audience didn’t see it like this but when I think back on it, the conversation was so crazy. It was like we were both insane and we were in a waiting room, waiting for our doctors to come in. “The doctor will see you now. Mr. Wright, the doctor will see you now.” This was the conversation in the waiting room, two insane people. That’s how I saw it.

He’s been gainfully employed since leaving The Late Late Show, but I hope he gets another show that brings out his full potential.

Yeah, I hope he gets another talk show, too, or something like that. It was an interesting thing for me, too, because I would always, for years and years and years, I knew exactly what I was gonna say. I would write all the jokes and I knew them before I went in front of the audience. It took me a while before I could trust myself to just joke around on television, just joke around with someone in front of an audience. It was very different for me and to do it with him, like I said, I could trust him. If I said something that wasn’t funny, he would make it funny anyway.

Yeah, he could turn the situation around so well, not just with you but with other guests. I don’t know what it is, he’s got it.

One other thing, I agree with you that he’s underrated and he never got the total respect that he should be getting.

I think if there were fewer talk shows he would, and I think he’s head-and-shoulders above some of the talk shows hosts out there now. His show was really entertaining.

Yes, I agree.

Can you talk about the catalysts in your career? I know (fellow Boston comedian) Mike McDonald helped inspire you, but what did Barry Crimmins do for you?

Well, I was very influenced by George Carlin and Woody Allen. George Carlin was on The Tonight Show all the time and he had the Class Clown album. Before I got into comedy, he was one of the reasons I wanted to do it. And then there was a radio show in Boston. I was a Boston Bruins fan, like during the Bobby Orr days, so I would have my radio in bed with me and I’d be listening to the Bruins playing.

And then one night, it was a Sunday, I was fooling with the dial and found this radio DJ that played two comedy albums every Sunday night. The guy played two entire comedy albums. It was right when I was watching The Tonight Show all the time when I was 16. I was the same age, now every Sunday I’m tuning into this comedy show. He had a huge amount. He had Bob Newhart. By the way, I love Bob Newhart. He’s a genius.

From interviewing both of you, I can see the lineage. I didn’t see references to Bob Newhart in anything I read about you but I knew you must have appreciated him.

He’s one of my favorite comedians of all time. And this guy played all these albums—Mel Brooks, all that stuff. He played Woody Allen’s stuff. He had two albums out before he made movies, and those two albums weren’t stories. They were jokes. He wrote jokes. So my main influences were George Carlin, how he talked about everyday things—all his stuff was about little tiny everyday things—and for how to write the structure of a joke, I was influenced by Woody Allen, from how he wrote a joke. So years later, when I first started doing comedy, those two were my main influences. What Barry Crimmins helped with was, he was very encouraging to me. I would only have seven minutes, eight minutes material and he would put me on in the Ding Ho comedy club in Inman Square in Cambridge. He would give me a spot on regular nights even though I only had eight or 10 minutes of material. I would say to him “I don’t even have as much material as the other people,” and he would say, “It doesn’t matter. What you’re doing is really different. Don’t think about it, just keep doing it.” He was very supportive to me, and I’m glad he’s getting all this recognition now from the movie (2015 documentary Call Me Lucky) and the comedy album he just did with Louis C.K. He did a comedy album that Louis C.K. directed … a comedy special, I mean.

You don’t see many documentaries that aren’t vanity projects anymore either, so it was nice that Bobcat Goldthwaite handled it.

Yes, he did a great job, excellent job. And Louie just directed a special of Barry’s. I don’t even know if it’s out yet. He directed a stand-up special. Barry’s a genius. He’s brilliant.

Have you and Louis CK talked about working together again since the end of Horace and Pete?

Talked to him yesterday about how the feedback from Horace and Pete has just been amazing, and how it keeps going and is still selling on his website. But I don’t know what’s going to happen. There’s not going to be another Horace and Pete. I don’t really know what Louie’s gonna do next or if I’m going to be involved in it. He’s another genius. I’m so lucky to work with these geniuses. I mean Barry and Tarantino and Louie.

Nurturing geniuses. I often hear from comedians how cutthroat the business is and it seems like you guys helped each other out in Boston in your time.

Yeah, everyone was very supportive. There was no show business in Boston. No managers, no producers, no agents. It was just pure learning the craft. Everyone was supportive of everyone.

Do you have anything scheduled apart from your stand-up schedule right now?

No, I’m just doing shows, writing and performing live. That’s my main thing I’m doing right now.

And you never turn it off, right? Your random-accessing part of your subconscious is always on?

Yeah, it doesn’t shut off. Even if some law … I don’t know why this would happen, but if it was illegal for me to perform anymore, it could not stop my mind. I’ve been writing since I was 23, and it’s just like any exercise you do, physical or mental. My mind is always scanning. It’s just joking. It’s fun to think. It’s fun to joke around. It’s fun to see the joke. It’s a fun thing to do. I love doing it.

I don’t know of too many comedians that plan for retirement. They seem to want to keep working. I asked Bob Newhart “How long will you keep doing this?” and he said, “As long as the opportunities exist.” His attitude was, “I want to keep channeling his as long as I can.” Is that how you feel?

Yes, absolutely! Like Don Rickles—he’s still performing. I was going to see Don Rickles in Rhode Island this weekend but I have to go do one of my own shows. I’ve met him a few times but I’ve never seen him do a show. But you talk about comedians retiring—I mean, thinking is fun. It’s fun to think. It’s fun to make up this stuff, and it’s fun to be in front of the crowds, too. It’s funny that you bring that up because I’m 60 years old now, and the last few years, of course I know people start retiring in their mid-50s, 60s, from other careers. And I see people retiring … I never really thought about it, never really noticed it. It’s like all of a sudden I’m 60 and I’m thinking, “Oh my God, I’m 60 and people my age are retiring from what they’re doing,” and I’m thinking, “It doesn’t even enter my mind to retire.” It would be like retiring from joking around. It’s such a fun thing; I don’t even really see it as a job. It’s like that thing “If you love what you do, it’s not a job.” That cliché is true. It’s like, I love making shit up and I love performing. … The mind is interesting to me. The mind is fun. I have fun hanging out with myself. I’m my own friend, and we have serious things, of course, but we also … I’ll think of things and laugh out loud by myself.

It’s like that with writing. It’s good to have something creative apart from your main outlet that you’re not necessarily known for, though.

You mean like music?


I have a couple of songs on my website. I like to fool around on the guitar almost every day.

You once said about Vegas, “I like going there because the place is so weird. It's the only place I play where outside the theater is weirder than anything I'm talkin' about.” Do you still feel that way or is the rest of America catching up in the weirdness department?

If Salvador Dali was hired to design a city, that’s what Las Vegas looks like to me. He’s my painting hero, my surrealistic hero. When I say that city’s weird, I’m saying it looks weirder than what I’m saying onstage. That’s what I mean. There’s so much creativity out there, it’s just unbelievable how many creative people there are in all different forms of art. I don’t know if the people are catching up to the weirdness but my analogy was a visual thing. I mean, the Eiffel Tower and the pyramid thing … it’s insane. The Statue of Liberty? It’s strange.