Nick DiPaolo: “I’d Like to See More People Cutting Loose and Taking Risks”


For more than 25 years, Nick DiPaolo has battled it out in the comedy trenches alongside peers Louis C.K., Colin Quinn, and the late Patrice O’Neal. The Boston native has also waged a few personal wars of his own–mainly those against political correctness and complacency. Headlining Caroline’s on Broadway Friday through Sunday (4/4 – 4/6), DiPaolo may miss the days of endless road gigs and creative risk-taking, but he remains optimistic that open, authentic dialogue will always be welcome on the stand-up stage.

See also: Hannibal Buress: “Bombing Can Be Good”

You made the move from Boston to New York extremely early in your comedy career. What did you think you had figured out at only two years in?
That’s a good question. I guess I thought I was better than I was. I grew up north of Boston, so in the late ’80s, when I started, that was like the Mecca. There was a whole stand-up boom going on, and comics were moving from other parts of the country to Boston to do comedy. There was just so much work, even as an open mic-er. I remember looking at my book; the first full year I had worked over 300 nights, and that was just because there was so much stage time. Every restaurant and every pub in New England–not just Boston proper–had a comedy night. So it was a matter of good timing.

As a kid I used to watch a lot of comics. I used to watch Johnny Carson; I was fascinated with his monologue, and I remember seeing Jay Leno on The Merv Griffin Show. I was fascinated that somebody could come out and just talk and make a crowd laugh without acting like an ass. So I started to do open mics, and there was so much work to go around, it was every night for a couple years. A Monday night I would be at a Chinese restaurant in Rhode Island, on Tuesday night I’d be at, like, the Holiday Inn in Nashua, New Hampshire, and I might be in Boston at Stitches, the next night I might be at a college like the University of Massachusetts. There was just a ton of work. And what’s funny is us comics thought that was normal; that’s how it would always be. But it actually helped. When you first start out, stage time is the whole key. So you grow by leaps and bounds. Then I had a guy named Barry Katz who told me I should start going down to New York, so I listened to him.

Was he running [West 3rd Street’s] Boston Comedy Club then?

Yeah, right after I moved down, he started the Boston Comedy Club. He was my manager, and he was Louis C.K.’s. Me and Louis were actually roommates for about a year. Looking back on it, it was so much fun: just doing three or four sets, just running around the city.
Budd Friedman and his wife ran The Improv on 44th and Ninth, and that was a big thing, to pass at The Improv. That was the first obstacle, was Silver Friedman. It took me like three or four chances before she said yes, and then I thought, “Oh, now I can move to New York!”

The New York comedy scene feels like it’s in a different place than it was even 10 years ago. I’m not sure if it’s because everything that’s shocking has already been said, that the internet has rendered audiences incapable of shock, or that political correctness is rendering the act of envelope-pushing obsolete.
I think you hit it on the head with the internet. I listen to these young guys on the radio, and I think stand-up is in good hands with these guys. But you’re right with political correctness, and people are so hyper-sensitive now, and I think these young guys coming up are like, “Look, if I want to get on TV…” That’s the one similarity, I’d say. Even when I was coming up, when you first start out you want your material to be accessible so you can get some exposure, I guess. My first 10 years was all TV-clean stuff. And then once you got a few credits on your resume, then you felt you had earned the right to cut loose and say whatever.

I think these guys coming up now, they grew up with Comedy Central, and they grew up hearing us on the radio. I didn’t have that coming up. Comedy Central had just started, but we didn’t have satellite radio, where you could hear a thousand comics a day around the clock.

I’d like to see more people cutting loose and taking risks, you know? It’s not about killing; some of them just tell mildly amusing stories. I’m 52 now, so that’s what’s scary out of all the things: to watch yourself change, but the demographics stay the same. It’s still people in their 20s; that’s really weird. But your act should grow with you. Obviously you should change over the years. You have these guys still telling the same jokes. It’s kinda sad to see some comic in his 50s talking about smoking pot in college. If you’re an artist, you’ve got to talk about what’s going on in your life that very second.

Do you think a show like Tough Crowd With Colin Quinn would be able to air today?

It’s a great question, you know? I would hope so. I mean, because if not, we’re just regressing free speech-wise. I don’t know. People seem to love it and miss it. I’ve had people come up to me, like, “Yeah I was 14 or 15; I loved that show!” I’m like, “What?” I can’t believe it. I’ll be at a club and have some good-looking girl in her 20s approach me. She’ll go, “My parents loved you on Tough Crowd.” I’m like, “What the fuck?”

But I don’t know. It was a very brutally honest show, and I think we need more of that. When it comes to talking about things like race, let’s have a discussion, you know? That’s the best way to do it. I really believe that. Through humor, we can get a lot more achieved than through politics.

It’s interesting to think about how someone like Patrice O’Neal would be reacting to stuff like that now.
Yeah, absolutely. I was joking about that today on Opie & Anthony, because I think some of the shit I said on Tough Crowd didn’t really help my career [laughs], because–let’s be honest–the business leans left, hard. And I don’t think I was did myself any favors, as much fun as I was having. And I said that on Opie & Anthony today, “Patrice is probably looking down, laughing his balls off.”

I think of the great Bill Hicks, too, and what he would have to say about Syria or Afghanistan or whatever. And Patrice, too. So I don’t know why they don’t do a show like that again. Different times and people running Comedy Central, maybe they grew up in these politically-correct times.

It’s not on Comedy Central, but you still have somebody like Louis C.K. retaining the power to keep his creative visions uncompromised.
Yeah, he’s a pioneer in that way.

Are you actively working on a follow-up to your own 2011 special Raw Nerve?
As a matter of fact, I just shot an hour this past November in Minneapolis. It’s called Another Senseless Killing, and we’re just starting to shop it around now. Not that I’m a political comic, but people always want to want to throw me in as a conservative whatever; I think because of Tough Crowd I get pigeonholed. But this hour, for me, it’s apolitical. It’s just observations, and nothing too heavy. It’s still funny and it’s raw and I’m anxious to get it out there because Raw Nerve was a couple years ago, so I’m kind of overdue. I took a year off to do radio, so I hadn’t done any stand-up. I went back to it and put my nose to the grindstone and drove into the city every night, working on material. It took me about a year and a half, two years. It’s a pretty tight hour. I shot it at a comedy club and not a theater, which is kind of the thing to do now.

Was it at Acme?
I did it at Acme, yes, which is probably my favorite club in the country.

Jackie Kashian did her All Things Comedy special there, and Dave Attell’s new show and his special, too, were shot in clubs. Everybody’s kind of getting away from the bright, shiny, boom microphones and kind of taking it back to a more real, underground place again.
Yeah! And it’s funny: I said to Louis–I went to Louis C.K.’s on Thanksgiving, and he asked me what I was doing, and I said, “Well, I just shot this hour at Acme.” And he goes, “That’s smart! That’s a smart thing!” I didn’t realize he was doing something with Todd Barry. It was kind of also that I couldn’t fill up a big theater. [Laughs] But it’s true; you catch more of…stand-up is supposed to be a little intimate. And I’m definitely better, as much as I love theaters, but I think you catch the true essence, you know? You lose that in a place with 70-foot ceilings.