Nick DiPaolo Killing It In His New Special

interview nick dipaolo comedy special

If you’re really into comedy, you know is one of the products of Boston’s comedy boom and part of the pantheon of guys from the “The Table” at The Comedy Cellar who became household names through shows like Tough Crowd and The Comedy Central Roasts. But plenty of folks also know him from his former radio show with , his current podcast, as one of the guys playing poker on Louie, and, of course, from his long and successful stand-up career.

His latest special Another Senseless Killing is available for direct purchase at his site or for pre-order at Amazon & iTunes, dropping February 17.  The IBang talked with DiPaolo about coming up during the comedy boom and what it’s like to be the jock in an industry of nerds.

The IBang: So, for this special, it’s in a club and it feels like you’re actually in a club, not a theater. Was that a conscious decision?

Nick DiPaolo: Yeah, a lot of us sit around at that table a The Cellar started to talk about this a few years ago. I’m basically a club comic, that’s how I’ve made my living. And that’s basically how you develop your act in these intimate clubs in New York City. It’s more indicative of what we do every night. For the guy or girl watching it, it’s more like you’re in the actual audience.

If you ask most comedians, they’ll say the key to a good club is a low ceiling that keeps the energy right in your face.

I think the special captures that energy and it captures what I do for most of the year. This club Acme in Minneapolis is one of my favorite clubs. If you ask most comedians, they’ll say the key to a good club is a low ceiling that keeps the energy right in your face. That’s where stand-up was first done, little basements in New York. So it was a no brainer in terms of what club I wanted to do it in.

It’s funny, I mentioned this to my old buddy , who’s now so famous he could fill an airplane hanger, but when I told him last Thanksgiving that I was gonna shoot it this way he said, “That’s smart, I’m doing the same thing with .” And did his last one with footage from clubs all over the country, so we’ll see.

The IBang: So you mentioned that the room makes a difference, I remember for a while you were doing shows upstairs at Stand Up NY Labs, which is about the most intimate you could probably ever get.

Nick DiPaolo: That’s maybe a little too intimate! [laughing] Sometimes it worked there and sometimes it didn’t. But that was more just to get the words out, it’s not about getting laughs.

The IBang: That’s an interesting thing, for a guy like you, it’s not like you can just walk around doing open mics. Is that the kind of thing you have to do to work on new material?

Nick DiPaolo: For the most part, you have to have somewhat of an audience. So, I’ll go do New Talent Night at Caroline’s. It’s this thing called a bringer show that they didn’t have when I started out, but people get all their friends and family to come watch them. I don’t know what that proves, making your friends and family laugh, but so they’ll have like 150 people on a Monday sometimes. And if I go on the road, I’ll pick a spot within the hour to throw in some new stuff.  People don’t realize how long it takes to develop material. I mean, we all write at a different pace. Louis is so prolific, he can put an album out every year of some quality. I think we all could do that, it just wouldn’t be the quality you want.

Some people sit down and write it out longhand, which is what I used to do, then I got too fucking lazy. Now I write on stage more. I come out and I’ll riff on stuff I’ve already developed or whatever pops in my head at the moment. That’s why you have to record yourself every night. Unless you have a mind like a steel trap, you’re not gonna remember what you said. Even when you’re listening to proven material, you might hear it and go, “Oh, I can spring off that in this way..”

It’s Comedy 101, really. used to say, “The reason I have so much material is that if I have a funny thought, I take the time to write it down.” And Louis – I keep bringing up Louis because he was my old roommate years ago – he actually has the kind of mind where he never had a fucking notebook! When we were young comics, I’d be like “you’re not writing anything down??” but I didn’t know he had the IQ of an astronaut.

The IBang: I think in comedy more than most forms of entertainment, you have those situations where you have those stories of “I can’t believe these two used to be roommates!”

when I first went to The Comedy Cellar, was there reading a newspaper and I went up to him and said “Hi, I’m Nick DiPaolo, I’ve got a 9 pm spot…” and he didn’t even look up from the paper, just goes, “Yeah?”

Nick DiPaolo: He’s got a HUGE DICK! Is that what you’re getting at? He’s got a huge dick for a redheaded freckled face.  But yeah, we lived together when we first came down to New York and he’s just a smart, eccentric, likeable.. I’m not trying to kiss his ass, he’s just one of the most interesting people I’ve met in my life. I don’t have any crazy old stories like “I fucked Elayne Boosler!” I came down from Boston with Louis and it would be me, him, and Dave Attell and after we’d do our sets, we’d just go to a diner right around the corner from The Comedy Cellar and sit there until 4 in the morning, bullshitting. It’s exactly what the generation before us did, the Robert Kleins and Jerry Seinfelds, which I think is kind of cool.

When I met Dave Attell, he used to wear a suit jacket on stage and had a comb-over, he looked like a weatherman! It’s just funny to watch all of us develop our own personalities. When I first came down, I started working at Catch a Rising Star, which was THE club at the time. I sat around for six months before I got on stage, but I’d be there and see come in with literally his robe on and a drink in his hand. was at his peak, Jerry would come in and it was just fucking amazing. That’s when I really met , who is one of my best friends in comedy.  I’d sit there until 2 in the morning and finally said “Oh, you’re going on next” and I had to follow and Dennis Leary and I held my own.  Then when I first went to The Comedy Cellar, Bill Grundfest was there reading a newspaper and I went up to him and said “Hi, I’m Nick DiPaolo, I’ve got a 9 pm spot…” and he didn’t even look up from the paper, just goes, “Yeah?”

I watched this guy , who is now hugely successful, he’s written for The and The Family Guy. So, he’s onstage and he’s killing, so I’m already intimidated, and then he closes with one of the funniest things I’ve ever seen, he does an impression of Lee Harvey Oswald being shot by Jack Ruby and the part of Oswald is being played by Jackie Gleason! He tore the roof off the place. To this day, I’ve never seen somebody kill that hard.

 The IBang: Do you think it’s important for young comics to watch other comedians?

Nick DiPaolo: No! I think it’s just the opposite. Yeah, we all are influenced by famous people, but that’s different. I try to stay out of the room, so you can develop your own voice. You hear a premise that catches you and a couple months later you pull a Brian Williams and convince yourself you wrote it. I don’t trust comics who sit in the room for the whole show. That’s my Italian paranoia.

But we’re all influenced by famous guys when we’re younger. I loved George Carlin and I watched Pryor three times in the theater. I loved when he’d be on the Letterman show in the 80’s. If you google it, it’s still the funniest. And Letterman, I saw him on The Mike Douglas Show when I was 13 and that’s really what inspired me to do this.  I’ve done Letterman twice now, but I didn’t get a chance to bring that up. I wish I’d said, “You’re really the one that inspired me to do this,” and then slapped him in the face and said, “Thanks, now I’m lonely and horny.”

The IBang: How did you decide to really do this? I mean, you have a fairly normal life now, but I’m sure starting out it wasn’t so great.

What, am I going to apologize for having a happy childhood?

Nick DiPaolo: I’ll tell ya, my timing was good for once in life. I never really lived that bohemian lifestyle. I started in the late 80’s and stand-up was in the middle of the boom. I quit my day job in like ten months or a year. There was so much work in the New England area. Every restaurant and pub in New England – not just Boston, I’m talking CT, RI, VT, NH – every place had a comedy night and was booking these rooms. I had done a few open mics and he saw me and wanted to take me on, so my first full year I think I worked like 300 nights. I was still really just an open mic’er, but I could make $600 cash on a weekend, so I got really lucky.

There were more stages than there were comedians! Clubs could afford to fly in a feature act, pay you $700 for the week and put you up! A feature act, can you imagine? Now, I’ll do a gig in Michigan and my feature drove up from Florida and they’re only giving him like $500. I go, “Holy shit, boy do you want it bad!”

The IBang: On the scale of things, you’re much more an alpha male than a lot of comedians. Do you buy into that theory that comedy has to come from the underdog?

Nick DiPaolo: I’ve thought about this a lot, just because I really don’t fit in in this business. It’s funny, Colin Quinn says it, “DiPaolo fucking approaches this from a winner’s perspective!” God forbid! But I think all that is a bunch of nonsense. I mean, I’m sure I’m damaged in some way. I think it’s more people are damaged, not that you need to be an underdog. But when I’m sitting around with a bunch of other comics, I still to this day feel like I’m playing in their backyard, not mine. I wasn’t an artsy guy, I was an athlete.

But I don’t think you have to have been beat up in high school to be a good comedian. It’s about being funny, about having a fucking funny bone. What, am I going to apologize for having a happy childhood?

Follow NickDiPaolo on Twitter | Order Another Senseless Killing on Amazon | Visit Nick’s Website

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Amy E Hawthorne is a New York by way of LA comedy journalist and founder of She's also a produced numerous stand-up shows, got a paycheck and a drinking problem from The Comedy Store and is convinced that the Big Avocado lobby are the ones who really pull the strings in this country.

1 Comment

  1. fredbydawn

    February 13, 2015 at 10:05 pm

    One of the greats. Easily in my Top 5 working stand-ups. And the new special is very funny.