On the Road with Gary Gulman

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Gary Gulman is on tour right now in support of his upcoming third standup special, It’s About Time. Like his jokes, the title has several layers and meanings. But you could add one more: it’s about time Gulman is recognized as one of the best standup comedians working today.

Now 20 years in, Gulman is one of the most consistent performers around in the vaunted New York comedy scene. He’s done specials for all the major comedy networks and is one of the few comedians who can boast of appearances on all seven late night talk shows. His joke writing is legendary, and he’s got an uncanny ability to come up with hysterical bits no matter how minute the subject matter.

I recently had the opportunity to talk to Gulman about his new tour, working with Louis C.K., therapy, and some of his unproduced sitcoms.

Congrats on the new tour. It’s About Time. There are a lot of different takes a person could have on that, a lot of different interpretations. What were you going for?

There are a number of entendres there. “It’s About Time” because it’s my first proper tour in 20 years of doing comedy and generally you get really good after 20 years. I think that seems to be the mark that a lot of comedians talk about as being when they really figured out what they were doing, which is daunting, but I’m glad I’m on the other side of it. And it’s going to culminate in my 3rd special which requires having a lot of material, which is in comedian language “time.” It’s a lot of time, you can do a lot of time. And there’s one other entendre that I can’t even think of right now. But those are the main ones and is that three? Is that a triple entendre?

It is. That’s a lot of entendres. What culminates after 20 years of doing comedy? What clicks at that point? Obviously it’s probably a little harder for you to say because you’re living in it, but if you could step outside for a minute and analyze it.

I guess when I first started in the 90s, I used to write down every joke word for word and then slowly it became more about working it out onstage until after 20 years it’s mostly you have enough opportunities to do long shows and also you can run a stage pretty much wherever you want. You get the opportunity to work a lot of the stuff out onstage, which is really the best because you really have to write with the audience. They can be encouraging, there’s some implied criticism there while I’m doing it. If they’re not laughing then you’re not on the right road. It’s just much more efficient to write onstage because you’re getting instant feedback. That’s been my technique. I still listen to my sets just in case I came up with something off the top of my head or ad-libbed. Essentially the biggest difference would be my creative process is more efficient so I am able to build time quicker. The first few years, God, it took me three or four years just to get 10-15 minutes of material that wasn’t horrendous and that I could put on TV. I think I did like 4 different TV sets in the past 12 months. Something I definitely couldn’t have done probably in the first 8-10 years. It didn’t come quick enough.

That’s fascinating. On paper you’ve had a lot of success in comedy already. To think that it still takes all that time for you to get to the place you want to be is, as you said, daunting.

The other side of it is that I wish I knew when I was lamenting 10 or 15 years ago that I would never be any good or worth watching that if I stuck with it I would get to a point where I was proud of what I was doing and wanted to get it out there. There’s a trend where guys are so excited on social media that they’re inviting everybody in the universe to come see them perform and they’ve only been doing it for a few months. It was sort of the opposite for me. I didn’t really promote myself because I was insecure about what I was doing for a really long time and now with this tour for the first time I have been feeling really proud of what I have to share with people so it’s easier for me to promote without feeling like I’m pulling one over on them.

I commend your integrity.

There are just so many great comedians who I would recommend seeing instead of me in the past 10 years or so. I feel like I am in the group that I would pay to go see now, so that feels good.

Your name is always mentioned as one of the best guys in New York.

Thanks. I don’t know why you had to mention New York. [Laughs.] That’ll kill me. I’ll think what about the east coast? Is New York any different from the east coast? I understand what you’re saying but of course I’ll read into it.

At the end of the tour, you’re going to film a special?

Yes. And it’s going to be called It’s About Time. The other thing in my special is that I do talk about the time passing. Just how life goes by once you turn 30. One of the things I talk about is how when you’re a kid you really look forward to the Winter Olympics and once you turn 30 it just reminds you of how little you’ve accomplished in the last four years. You look back and think nothing’s really changed but some people have tried out for and made the Olympics and I had a bike but the chain broke like 5 years ago and I haven’t brought it into a shop. There’s a great disparity between the drive of Olympians and my personal drive.

That’s funny. And you’re how old now?

I’m in my forties. [Laughs.]

Got it. We’ll leave it at that. You look great, Gary.

I do look really young, I must give myself credit for that. My excessive sleep and eating right has helped me.

Do you feel like you’ve got everything mapped out in terms of what’s going to be on the special? Will you change anything based on how the tour goes?

I don’t know that I’ll change anything but I’ll add some stuff that I’m working on now. The good thing is that with stuff that’s unfinished, I can keep that for the next special. Thanks to – originally George Carlin – but Louis and some other guys who put out a new special every year or so, that’s become the standard. Whereas when I was growing up guys didn’t put their stuff out there and they would be able to tour with the same stuff for a long time and I think you perfect it, but at the same time it gets very boring and any comedian will tell you that the best part of doing this is coming up with something new. So if you’re doing that more frequently it’s really a gift as a performer and to your audience which you’re able to see so much more frequently. When I was first a big fan of comedy when I was a teenager, I wouldn’t have even known how to find guys, now I can find them and see what they ate for dinner on Instagram or what they think of every social issue of the day. So it’s different. I don’t know that it’s better, but it’s definitely better for creativity, the fact that you’re expected to turn your material over every year, which is really helpful to the art as a whole.

Absolutely, it’s definitely changed the game. And this upcoming special will be on Netflix?

I think eventually it all goes to Netflix, but usually I like to get it on television first, or a half hour on television first with Showtime or Comedy Central. And that might mostly be ego and giving my parents the ability to watch it because they don’t really know how to use a computer. It’s for ego.

I wanted to ask you about your brain and joke writing. You seem to find jokes in just about everything in life – like your bit about grapes – is your comedy brain always working? Can you ever just sit down or are you constantly looking at things like “What can I tell a joke about that chair over there?”

[Laughs.] I’m definitely in my head a lot. I’m ruminating a lot on these ideas, and so I would say that it’s fun because sometimes I’ll just be alone and I’ll think of something and write it down and think “oh I can’t wait to do this onstage.” The other thing is that it’s kind of a trick in that I work in what they tell me is called “longform” comedy where it’s stories and extended bits, so I’m able to work a lot of these smaller ideas into bigger stories. I have this one story about Trader Joes and it’s fun because it wraps into different stories about people in a line and the food that they have and the nature of their business and things like that so it’s really just the idea of trying to mine every idea during a story to see if there’s more there. And a lot of times, it doesn’t push the story forward, it’s just an observation I’m excited to share. It helps me again with building time. It’s so hard to come up with a new premise that it’s much easier to add things to an idea that you already explored. So it’s a matter of using my writing time to try to make something deeper and more nuanced and layered. I guess layered is the word that people have used to describe the style.

Makes sense, and to me it’s a testament to the idea that anything can be funny if you put the work into it.

I think one of the best things I’ve ever read is Emerson’s Self-Reliance. He talks about the idea of the personal being universal, and that really stuck with me because it’s like, alright, I can say this thing and it seems like I’m alone and nobody else has this thing, but it almost invariably is universal. I’ve always been moved when you’re at the credit card line and the cashier holds the receipt for you so you can get a better signing grip on it if you don’t have a free hand, but I thought oh nobody’s going to care about that. Then I said it on stage one night and the people really thought it was an interesting observation so it was very encouraging. And it’s just that idea that very rarely are you the only person who notices something or had a feeling about something. I guess it’s something that is intuitive.

Going back to your Trader Joes bit, I think I saw you do that in Boston. It was great. It was when you opened for Louis C.K.

It had just happened when I was touring with Louis so it probably took about 5 minutes to tell the whole story and I could do it for 35-40 minutes if I have time. That was right after the incident, the crime, so yeah it would be interesting for you to see it now. Opening for Louis was just like a clinic every night. It was just amazing.

Why is Louis so on top of it right now?

The content is remarkable. He has his finger on the pulse of America – his delivery is such that I saw him do the same story twice a night on the same weekend and if you didn’t know, and of course I knew, but you would think it was his first time ever saying it. Just his presence and his acting ability and his choices, just everything. He was so professional and he would add things and take things out and adjust them. And the other thing that was really impressive was that he did Saturday Night Live during that tour and I worked with him that following Thursday after the taping and he had already dropped the 10-minute killer chunk he had done on Saturday Night Live. He said “I can’t do it anymore because 4 million people saw it.” And I was blown away by that. It was a long thing and obviously it was his favorite thing because he did it on Saturday Night Live and he just put it into the archives. It’s really something. It’s one thing to say you’re gonna throw it out after you do it on TV, but to actually do it five days later when nobody would hold you to it, they’d probably be thrilled that you did it again. But that’s really what it takes to keep evolving and improving so it was a real clinic.

That’s incredible. Some people might know you from doing Dane Cook’s Tourgasm back in the day. Will you take any experiences from Tourgasm on this new tour you’re doing?

One thing I learned from Tourgasm is whatever the cost, don’t stay in a bus. Stay in a hotel. It is exhausting to travel in the same thing you sleep in every night. There’s no relief. So I definitely will spend the money to stay in nice hotels and eat right and exercise and get my sleep. That’s the other thing I learned from Louis – and his tour was much more ambitious, more people wanted to see him so he had to do more shows. But he must have been exhausted because he was doing promotion and working on other things and he’s got a family and kids but you wouldn’t have known this from watching him. I can’t imagine that he wasn’t rushing back to get some sleep so that’s really important with a tour.

The other thing is bringing somebody along who you like. For most of the shows I’m taking Joe List who I’ve known since he first started doing comedy when he was like 19 years old in Boston so we’re really close friends and he’s such a nice guy and a funny comedian who really works hard and is delightful to be around. He’s really positive and he has a girlfriend so he doesn’t carouse. It’s important to tour with somebody your speed who’s not going to drag you out late. I need my rest. That’s really important. And just for mental health, being around a friend really helps.

I know you started in Boston and then you mentioned that you moved to LA. How long did it take you to go from Boston to LA? What made you take the plunge?

I started doing Boston comedy October 8th, 1993. Then I moved to LA summer of 1999. And that’s when for the first time I was able to do it for a living because that’s when they give comedians development deals to make sitcoms and they were quite lucrative and so I was able to move out of my mother’s house and move to Los Angeles and get a car and my apartment. I think I developed five shows while I lived there and none of them were picked up so that was very frustrating and disappointing. In 2006 I had gotten sick of not doing very much standup in LA because there wasn’t a lot of demand for my standup. There are just so many stars and so few spots in comedy clubs so at most I would do five spots a week whereas that’s a Friday in New York. So I came to New York in 2006, thinking I would only stay for six months, and I haven’t left. So that was probably the biggest change in the past 10 years, just moving to New York. And I think that made me a much better standup and performer.

How do you balance comedy in New York – it being the pinnacle of standup – versus the challenge of living there? Did you like living in LA?

The great thing about LA is that you didn’t have to hoard all of the nice days. It was gonna be a nice day tomorrow, where in New York you never know when you’re gonna get another beautiful, temperate day. So that’s one thing but what always made me happy was getting onstage every night. You’d get just as depressed in LA on a sunny day if you haven’t gone onstage in several nights, or I’d get up onstage at a coffee shop with 6 other comedians. You had to hustle and I was willing to hustle but even with the hustle you just couldn’t do as many shows. And it wasn’t like I was going out on TV and movie auditions all the time, it didn’t make sense for me to be there. I was in an acting class for a while because I wanted to utilize my time there but that was never what I got into comedy for, to be an actor. I wanted to get up and make specials and do late night TV spots, so this is definitely the best place for that.

Were your developmental deals all like autobiographical-type shows? I’d love to hear about them.

Yeah, they always are, right? The first one was about a guy who moves back home and the other one was about a guy who was an intern at a hospital and there was another one about a guy who was a football star who got injured dumping Gatorade on the coach. It was sort of a less funny just because I’m not as funny as this guy, but a less funny Eastbound and Down. I’m not quite the comedic actor of Danny McBride, but it was along those lines of a guy who really screwed up and had to start over, but it was long before that show, this was from 2001 I think.

Oh yeah, I almost forgot. Congrats on doing every talk show!

It’s one of those things that I had realized I’d done it as I was about to do it. It wasn’t something – although I remember my previous manager when I was very down on myself said, “How many people have done The Tonight Show and Letterman? That’s very impressive, you shouldn’t be down on yourself.” So then I knew that I had done all the late night shows, not with all the different hosts, so I didn’t get to do Conan’s Tonight Show and I haven’t done Fallon’s Tonight Show yet, but I’ve done all the brand names of the TV shows and Carson Daly. It doesn’t make me think I’m great or anything, it just seems to be a nice validation of my versatility, I hope.

It shows you have about as much mass appeal as anybody. At the end of the day the goal of a comedian is to have as many people as possible find you funny. Doing every late night show is an indication of that. It’s funny, once you’ve done say the Tonight Show or Letterman, you’d think you can do all the late night shows, but it just doesn’t work that way.

As much fun as it is, it’s not easy to make a tape of you doing really well with five minutes of TV material to give to the person making notes. Part of it is the function that I’ve been doing it a long time and my natural joke writing lends itself toward that style so I haven’t had to adjust too much.

Can we talk about therapy for a little bit?

[Laughs.] Yes! The thing I’ve been involved in since orientation freshman year of college!

I’ve heard you talk about it on other podcasts. Does it help you as a comedian?

I see a unique therapist in that walking into his office when I get there is usually another successful stream of comedians in New York heading out. At least a dozen other New York comedians that I work see him so it’s always one of them coming out and saying “Did you leave anything for me? Are there any laughs?” So he understands the scene and the nature of the business and all the whining we do and the worrying and the competitiveness. He understands that so you don’t have to explain to him what Montreal Comedy Festival is or what the booker from Letterman used to be like before he was let go of booking Letterman. He heard it from three other people that day. So it was really helpful. And just his style of work is being more honest onstage and being more self-reflective and open. I was very private and very shut off when I first started seeing him and I think I’m much more honest on stage now.

He’s just the latest therapist I’ve had. I’ve been in therapy on and off literally since I wanted to quit my football team freshman year of college during summer camp. I suffer from clinical depression so that combined with some anti-depressant cocktails that I take daily really helps me be a more productive member of society and I can relate to people and develop adult relationships and have meaningful friendships. And on top of that I think it’s made me a deeper comedian and a better thinker. Especially after, maybe you’re sick of hearing comedians talk about their feeling on Robin Williams, but especially after finding out that somebody so wonderful was so deeply unhappy and in pain, it’s just makes you think that the answer is not to become more successful but to become I guess, to accept yourself. I know there are comedians who don’t want to go to therapy because they think it will screw up their act, but I disagree.

That’s a really good insight.

One day it will make a fascinating book if someone covers mental illness vis-a-vis standup comedians. I don’t think it’s more prevalent among standup comedians than it is among the general population, I just think standup comedians are more willing to open up about it.

A list of Gulman’s upcoming tour dates can be found here.

Photo by Mindy Tucker.

Phil Davidson writes about, performs, and produces comedy.