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Interview: Nick DiPaolo

bill bodkin speaks with stand-up comic Nick DiPaolo …

Nick DiPaolo is probably one of the funniest and most honest people you’ll hear onstage or speak with. He’s referred to as a comedian’s comedian because there’s no facades, no act, it’s all Nick DiPaolo, all the time.

The former radio hot 92.3 Free FM in New York and longtime stand-up comic will be performing at Uncle Vinnie’s Comedy Club in Point Pleasant Beach, N.J., May 20 and 21. Pop-Break’s Bill Bodkin spoke with DiPaolo about his early days in the Boston comedy scene, his career on radio and his political leanings.

Pop-Break: When and where did start out as a comedian?

Nick DiPaolo: My first time on stage was in the summer of ’86. It was an open mic at Stitches Comedy Club in Boston, hosted by George McDonald. I did it [become a comedian] because I was fascinated with it, even as a kid. The Johnny Carson monologues, Jay Leno on The Merv Griffin Show. I lived 15 minutes from Jay and I was like, “Hey, this guy sounds like me!” And these guys weren’t using any pops to make people laugh.

I was a wiseass as a kid, so it was a logical leap.

I went to college and after I ended up working a couple of yuppie jobs. I spent a lot of time in the office and people there thought I was funny. And at the time [late ’80s, early ’90s], Boston was the mecca for stand-up comedy.

So in the summer of ’86, I was at a family cook-out in Danvers [a section of Boston] and my roommate kept pushing me to get to an open mic night. So I drove in Boston. I think I it was a Saturday night and I remember the marquee reading “Comedy Hell.” And that’s what it was.

Then I got a job in Rhode Island and moved there working for a steak and seafood company. I sold frozen food out of the back of my car. I remember I did one open mic in ’86 and I didn’t go back, because I moved, for another 8-10 months.

When I moved back, I put my name in for the open mic at The Comedy Connection in Boston. Every pub and restaurant at the time had comedy nights. I did 300 nights in my first year, which was invaluable.

It was crazy everywhere. Monday night I’d be in a Chinese restaurant in Rhode Island, Tuesday I’d be at a ski lodge in Vermont, Wednesday I’d be in Cape Cod at The Red Parrot, Thursday I’d be at a comedy club, Friday I’d be at a college. It was invaluable, really helped me develop an act. At the time it was me and Louie C.K. working all the shitholes.

PB: You were a member of the writing team for Chris Rock’s HBO series from 1999-2001. How did you score that job and what were some of your favorite jokes/sketches?

ND: He had seen me at comedy clubs in New York and I knew him a little but. It’s funny, I was doing a gig in Pittsburgh at The Funny Bone. It was the second show on a Friday night, and five minutes into my set, the owner passes me a note and it says, “Bring up Chris Rock.” I was like, “What the fuck?” And there’s Chris Rock waiting on the side of the stage.

He was shooting a film at the time in Pittsburgh. So we went to a strip club afterwards, and we hit it off.

One of my favorite sketches and Chris said it was one of his all-time favorites — we did this sketch comparing black and white boxers. We actually went out to Brooklyn and interviewed Mark Brieland, and we interspersed clips of white boxers getting knocked out between his answers.

Another one of my favorites was for a cold opening for the show. It was a play on the X-Games called the Malcolm X Games. We had these black guys in Nation of Islam outfits jumping out of planes, on skateboards. We ended up showing that sketch before the taping of every show to warm the audiences up.

We also did one where we made fun of the “12 Days Of Christmas.” We brought in an all-black choir and changed lyrics to “My boo gave to me a Glock 17…”

On the staff, you’d come up with an idea and then Chris and Ali LeRoy [Rock’s right-hand man], would flesh it out. They were great together.

Louis C.K. had worked there a few years before and was on the staff the year they won an Emmy. Louie’s great. He started when he was 17, 18 as a stand-up when I was like 25. We had the same manager and we ended up moving down to New York Together. I have a deep respect for him, he’s really bright. He helped Chris and Conan out when they got started [on their respective series]. He was one of the youngest producers in TV history when he worked with Conan.

PB: You had a show on 92.3 Free FM a few years back. How did you end up on radio, and is there any chance that you’ll end up back on the radio since your show was quite popular?

ND: When a comedian/headliner goes to a city to perform, he has to do morning radio. So it’s like 6:30 in Green Bay and you’re on the radio. What I found out from doing that was people would call in and they’d be laughing their asses off. And that would effect ticket sales [positively]. I liked it that I could make people laugh without getting heckled, I could really hold people’s attention. So I told my agent to land me in radio.

John Minelli of Free FM, who had gotten Rush Limbaugh and Bob Grant their gigs, called me in and I basically auditioned live on the air. Unfortunately, the station was hemorrhaging money and on their last legs. I was just getting good on the radio when they pulled the plug. Six more months, and I’d be filthy rich by now!

As a comedian, it was heaven being on the radio. I was playing bigger clubs, I wasn’t playing in half-full rooms, and my price went up.

DiPaolo was one of the bright spots in the short-lived 92.3 Free FM station

It was beautiful, you could be on the air and say, “I’m playing the Tarrytown Theater,” and 500 people would show up. It was great — two good incomes. And the people would be coming just to see you.

Radio’s just a mess these days. Sirius doesn’t pay. It was the worst time [for me] to get in. There’s people with 10 years experience who can’t get back on the air. Podcasts and the digital world killed terrestrial radio — they weren’t prepared for all the new technology.

But, as we speak, I am talking to a radio station up in Boston about having a show there.

PB: You’ve been a staple on Comedy Central Roasts. What was your favorite?

ND: I’m glad I haven’t been called for the bad roasts — but my favorite was definitely Pamela Anderson’s roast. That was my shining moment.

PB: You’ve been on a lot of political talk shows — Hannity, Red Eye, Fox News. Why would they come to comedians to be on their show?

DiPaolo is a frequent guest on Hannity on FoxNews

ND: They don’t come to me, I just tell my agent. “Call Hannity,” “Call Red Eye.” Comedy is one of the few professions that speak uncensored and say what they feel without getting in trouble. I mean look at Lenny Bruce in the ’60s. He was one of the leaders of the counterculture movement.

For me, I get on those shows because I’m one of the few comedians who lean to the right. And I grew up in Massachusetts and lived in New York and L.A. — you don’t get three more liberal places than that. But I’ve got a mind of my own.

I remember I revealed my politics on Tough Crowd With Colin Quinn one night, some people were appalled, and others loved it. I remember Colin telling me, “You could tell a joke about McDonalds, and we could tell you lean to the right.”

Look, I play the Comedy Cellar on the campus of NYU almost every night. You can’t get more liberal than that with everything they’ve been taught by their liberal professors. But these kids [in the crowd], they don’t laugh nervously [at my jokes] and you can’t get more PC than a college campus.

[DiPaolo commented that even on right leaning shows, hosts get nervous at his jokes]. I was on Hannity, who I’m not as conservative as despite what people believe. I made this joke one time about Obama purposely left a lot of pork in stimulus bill to prove he’s not a Muslim. I mean, his face went ghost white.


Even on Red Eye, they always use comedians, but they still get nervous about some of my jokes.

But then Bill Maher can go on TV and spew all his left-wing horseshit, and everything’s fine.

PB: You’re playing Uncle Vinnie’s this summer. What’s been keeping you coming back to this club all these years?

ND: I love them — they’re two genuinely hardworking Italian guys who love comedy. They give me a lot of leeway, and it’s a great place for me to work out new material.

PB: For those who’ve never seen you perform live, what can they expect?

ND: Expect a kind of angry white man point of view. It’s politically incorrect, but not purposefully so. I’m brutally honest — the audience is going to remember the show one way or the other.

Bill Bodkin
Bill Bodkinhttps://thepopbreak.com
Bill Bodkin is the editor-in-chief and co-founder of Pop Break, and most importantly a husband, and father. Ol' Graybeard writes way too much about wrestling, jam bands, Asbury Park music, HBO shows, and can often be seen under his season DJ alias, DJ Father Christmas. He is the co-host of the Socially Distanced Podcast (w/Al Mannarino) which drops weekly on Apple, Google, Anchor & Spotify. He is the co-host of the monthly podcasts -- Anchored in Asbury, TV Break and Bill vs. The MCU.


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