Gary Gulman is adorable; he’ll admit it. With that, accompanied by his always-evolving act, the Last Comic Standing and Tourgasm alum has performed alongside some of the greatest comedians ever to stand behind a live microphone. Since kicking off his career in Boston, Gary has become a household act all across the country, appearing on Letterman, the Tonight Show, CONAN and on Comedy Central. He’s been featured on a multitude of podcasts and continues to be a consistent player at the New York comedy club, The Comedy Cellar.
His admitted addiction is to the New York stage time, something nearly incomparable anywhere else in the country. He spoke to The Smoking Jacket about the stage, comedy and how his office water-cooler chat is without a doubt the best in the world.
The Smoking Jacket: What was the experience of starting comedy in Boston?
Gary Gulman: It was very challenging. When you start you have this blind confidence where you think you’re entitled to every spot. It’s, Oh, if I could just get on stage every night. That was the dream, to be well known enough that you could get on at any club. And there were really strong comics in Boston. As you get older, there were some who you realize are limited to Boston, but when they’re there they kill. They weren’t always nationally well known but locally they were kings of the city, and they were really strong. You could learn a lot from them; they influenced a lot of guys starting out. For the most part, they were very encouraging.
TSJ: Does every city have that? Those circles of comics who never break out but in their hometown are kings? And to the aspiring comics, they are teachers?
GG: I don’t know. Boston might be unique because it is possible for those guys to make a living without leaving. They established themselves at a time where comedy was booming and established themselves as local celebrities. I don’t know of any other city that’s like that. It would be interesting to ask around.
TSJ: How old were you when you started?
GG: Twenty-three. I was just out of college and was working during the day as an accountant and doing the open mic circuit at night. Then I’d show up late to work the next day; not because I was out late, I just hated my job. The longer I could sleep the better. [laughs]
TSJ: And did I read that you went back to substitute at your old high school?
GG: Yeah! About two years into the accounting debacle I quit and got a job as a waiter that, Robert Kelly, who I did Tourgasm with, got me. Through him I became friends with Dane Cook. That was ‘95/’96, when I waiting tables. Then I substituted for $45 a day and worked at a Starbucks. Finally, December 24, 1998 — that’s the last time I worked a day job.
TSJ: Wow, a specific date. That’s great.
GG: Oh yeah, I’ll never forget it.
TSJ: Comedy was starting to work out?
GG: I wasn’t able to make a living by doing just stand up. Networks used to make deals with comedians to do sitcoms, so I got that, and that let me be a comedian full time.
TSJ: So what’s it like going back home now?
GG: Well, one of the dreams has come true. I can go on wherever I want. They’re pleased to have me and other comedians are very complimentary. It’s nice to hear over the years that you’ve influenced or encouraged people to do stand up. That’s really cool. But with Boston, I think there’s probably a higher percentage of people there that recognize me than anywhere else. Not enough where it’s easy to get laughs though. [laughs] Jerry Seinfeld always said, “If you’re famous they only give you five minutes.” Well, you’ve also filled the place with people who have your sense of humor, so don’t understate the value of being a famous comedian, Jerry Seinfeld. [laughs]
TSJ: Do you think at a place like New York’s Comedy Cellar – a place that is notorious for famed comedians just stopping by unannounced to do sets, him included – is it harder for somebody like him because the crowd isn’t of his humor since they didn’t know someone like him was showing up?
GG: That’s a good question. I think the Cellar is different because people know they’re going to get a good show, so they kind of give the comedians the respect of knowing they must be good. But I remember in Seinfeld’s ‘Comedian’ movie he pulled into that club in Long Island and he just stopped in…
TSJ: They were a terrible crowd!
GG: They were! That’s a good question though. I wonder if there are ever nights where people like him think oh, these people weren’t expecting me and they would much rather have a different comedian.
TSJ: That documentary is a perfect example. You attain this level of fame but when you go to a club it’s more like, Okay, be funny. It was shocking to me that it’s still such a struggle for someone like him.
GG: I think the upsetting thing for me was that people were just rude and they had no reverence for him.
TSJ: As far as your type of comedy, where do you think it came from?
GG: I think a couple of things form that. When I was starting out everybody really revered Jerry Seinfeld, Jay Leno and Paul Reiser. I’d always try to find interviews with them. They came to the conclusion they wanted to be clean and that dirty was cheating. I quickly dismissed that; it’s silly and elitist. But back then, the idea of my heroes saying it was cheating, I wanted to be respected by them.
TSJ: That makes sense.
GG: Maybe, but it’s not very rebellious. Also, I noticed that during my sets that I didn’t do as well when I cursed. Maybe they [the audience] sensed my unease. It’s out of my comfort zone I guess. And I have developed a reputation for clean. Maybe some audiences are expecting that, I don’t know. But I feel like I throw in a couple of “fucks” to keep the religious right from praising me. [laughs] I’ve noticed that comedians like Jim Gaffigan and Brian Regan, while they don’t complain about it, they never set out to appeal to religious people. Sometimes I think it makes them feel uncomfortable.
TSJ: Uncomfortable that they’re embraced by them?
GG: No, I mean that they owe them a particular show. I remember I heard Brian Regan in an interview and he said someone came up to him after a show and said, “I thought this was a clean show. You said hell and damn.” After my shows people thank me for being so clean, but I said “fuck” a half-dozen times. I think the style I do sort of chose me. But when I came to New York full time in 2006, I felt I had to be a little grittier.
TSJ: Is it hard to make it otherwise in a place like New York?
GG: No, but I was convinced it was. Also — and this is good and bad — I wanted to be accepted by the guys at the clubs. Especially when I got here, everybody was very edgy. Eventually, I came to terms and accepted myself. I think when I first started I was very precious and aware that I could be liked onstage. I cultivated that; I was much sweeter onstage than I needed to be. And I think a lot of comedians try to please the audience when they start. So occasionally I’ll be gratuitously adorable. [laughs]
TSJ: I know you’ve said that after moving to LA and then coming to New York, you got addicted to the stage time here. What was it about the New York stage?
GG: I think if you were to ask any comedians, they can all agree that the best feeling is writing something new that works. You go home and feel creative, like a genius; prolific; you feel like you’re working hard; it’s great. You’re much happier about that than if a woman came up and said she wanted to sleep with you. I don’t know if it’s true for everybody, but it is for a lot of guys I talk to; that’s the thing that keeps them going.
On the other hand I think the guys that don’t try anything new, it’s depressing. The guys that do the same show every night because they’re not able to see themselves as anything more than businessmen. There’s an artistic manifestation to your work when you can write new stuff, so I think that’s the addictive part. But specifically with the New York stage time, it’s going to the clubs and hanging out with the other comedians. If you’re a comedian, during the day it’s solitary. You’re writing and then you get to be with people all night. The social aspect; it’s like that table in the back of the Comedy Cellar is the water cooler in an office. I spend three hours at a water cooler and fifteen minutes onstage. And it’s the funniest water cooler chat ever. My officemates are very funny and very deep and really interesting. There’s nothing like that.
TSJ: That is true. Comedians, to me, seem to be some of the most intelligent and thoughtful people. That drive to get up and do stand up is inexplicable.
GG: Yeah, and it’s rare for men to be so honest. And they do it onstage and offstage. That was the thing I was most surprised at when I started doing comedy, it was the honesty about things that are pretty embarrassing to a middle class Jew. These guys get onstage and talk about being drunk or broke or having sex. Then it became talking about being depressed and being on anti-depressants. Today, nobody gives a shit. Everybody talks about it. I really admire people like Sarah Silverman, Louis [CK], Doug Stanhope; these people that are trailblazers. For example, rape jokes were taboo seven or eight years ago and today it’s become so common. Comedians make light of everything; it’s great.
“I think a lot of comedians try to please the audience when they start. So occasionally I’ll be gratuitously adorable.”
TSJ: So how often do you try to write new material?
GG: I would say a lot. But as I’ve gotten more in my career I try to write onstage. I’m able to make it more conversational and real. But the best thing is to record it, listen to it and get yourself to do the hardest part: write it and transcribe. I’ll never memorize it but feel like I’ll get the jist of it. Eventually the joke presents itself. The lucky thing is that I don’t do one-liners so I can build a long joke. I’ve heard comedians say that it’s great if they can just add one line; Leno said that. Seinfeld said sometimes he’ll spend an hour trying to get rid of a sentence. It’s a lot of trial and error.
TSJ: And you guys will do that for a couple of years right?
GG: Yeah, but sometimes a joke has a shelf life. If you’re not adding to it, it’s time to put it away. I also feel that had I been more diligent with certain jokes I could have had them flushed out more completely quicker than they were when I put them on an album. Sometimes when you write a new joke you think its’ better just because it’s newer, but that’s not always the case.
It’s weird; nobody’s ever been able to pinpoint the poetry or science of jokes. People talk about Seinfeld being a joke doctor, how he could take other peoples jokes and make them better. I’d love to find somebody who’s seen that. I’ve sort of seen Louie act that way. He’s always been nice enough to watch my sets at The Cellar. He was popping in all summer for his tour, and I imagine Louie is what Jerry Seinfeld was supposedly. I spent a lot of time on this joke and just like that [snaps] he made it so much better. Now, he’s been doing comedy for 25 years. And once he said it I knew if was going to be funny. It didn’t even require much adjustment.
TSJ: Did he watch you do it?
GG: Oh, yeah, and he was very humble about it after it killed. He’s given me two or three more along the way.
TSJ: See, that’s the thing I love about comedians. They are some of the most humble people. Listening to comedy podcasts and interviews you can see how comedy is such an amazing community.
GG: It really is, and I acknowledge all the time how blessed I am to have so many interesting people who are so supportive and very encouraging.
TSJ: For somebody like Louie, what makes him so supportive? There’s so much competition in comedy but there are also so many good people in it.
GG: I wonder. With Louie, in order to become that successful you have to love it. And he does; you see that in him. Dave Attell is also very helpful. When comedians see other comedians helping them, if you’re a decent person, you are drawn to that. You want to encourage that.
Plus, there’s a confidence that comes with success where they can take some of their time to mentor people. But I don’t think Louie is successful because he’s nice, which he is, but I think he’s successful because he loves the work and makes you embrace the comedians that are good. Guys like Louie, Dane, Gaffigan and Regan; these guys who are turning over material so frequently, it’s really raising the bar. It’s good stuff.
TSJ: Speaking of Dane Cook, what was it like performing for his crowds on HBO’s Tourgasm? Those big rooms?
GG: Ninety percent of the time, it was really fun, if I could have put aside the idea that they weren’t there for me. I know I’m a good comic and was part of a good show, but I couldn’t get past thinking my friendship with him put me on the show. He has really good audiences, and as much as people make fun of his audiences they are pretty savvy.
I really felt the anger and backlash Dane got was misplaced. Even if you’re not a fan of his jokes you can’t say what he’s doing there is hurting anybody. But Tourgasm was a mixed bag. Also, I like to try out new jokes and you just can’t really do that with crowds that are 15,000 strong in some cases. Maybe I could have but I wanted to do well.
TSJ: Can you compare that at all to Last Comic Standing?
GG: No, because in Last Comic Standing I knew everything I did had the potential to be seen by a million people, where as Tourgam was really on spec.
TSJ: He didn’t sell it when you guys were doing it?
GG: No, he paid for it himself. The way he said it was, “I’ll probably just end up selling it to my fans.” So I thought nobody was going to see it. [laughs] Then it got on HBO.
TSJ: So I’m curious, you’ve done all of the Late Night shows. Is there a certain set or moment that sticks out in your mind?
GG: I think the first television appearance is always the biggest one. But the reason my early sets don’t really stand out to me is because I look back at them and think I was such a rudimentary comedian. The jokes killed and everything but they were just so simple.
TSJ: But your set on Conan last October went great.
GG: Oh, thanks! I thought it started out slow because the audience is at a weird angle. It had been four years since I had done a late night set; it was a great experience. All of those guys are great. Conan’s up there and Andy is so nice. Everybody at that show is so complimentary. That was a great time.
TSJ: So what do you think it takes to actually do comedy for a living?
GG: I’d say that blind confidence helps. There are guys who are not optimistic and very depressed and they make it, but I think it’s a much less enjoyable route. That really helps, being positive. It’s hard to make a living at it, but I don’t think that has to be the be all, end all. If you love it then great. If it wasn’t working out for me I could see myself getting by on odd jobs. I did before, you know?
TSJ: You mentioned there’s no amount of money you could get paid to stop doing stand up comedy.
GG: Oh, yeah! There’s no amount. None.
TSJ: That’s fascinating — so there’s nothing like it.
GG: It’s incredible. I mean, I’ve never been a rock star. I imagine that is great. Although there seems to be a much higher usage of drugs than in comedy.
TSJ: True. But you do hear horror stories in comedy.
GG: Oh, yeah, quite a few.
TSJ: Why do you think so many hopeful stand ups fall by the wayside? Is it just the rejection that gets at them?
GG: Yeah. I think if you’re in it for the wrong reasons, to get famous or super rich, you’re screwed.
TSJ: Is there ever a moment where you’re like, “I’ve got it!”
GG: [laughs] Yeah, it inevitably comes right before I bomb.