Interview with Nick DiPaolo

By Diana Bierman,

Nick DiPaolo is probably best-known for his half-hour comedy shows on Comedy Central and his latest hour-long album called “Raw Nerve” (available on iTunes). However, he’s also done radio, acting, and written for shows like The Chris Rock Show. Nick recently spoke to TheCelebrityCafe.com’s Diana Bierman to talk about what he’s done in the past and what he plans on doing in the future.

TheCelebrityCafe.com: I know your first hour-long comedy special digital album Raw Nerve came out in April and became available for download just last month. Congratulations! How does that feel for you?

Nick DiPaolo: It feels really good. I’ve done three half-hour long specials on Comedy Central, and it’s nice to do something like Showtime where, you know, you can actually cut loose a little bit more. I think it was kind of long over due actually. But it’s going pretty well, so I’m pretty happy with it.

TheCelebrityCafe.com: That’s great! I know being a comedian there’s always the chance of having people you offend. Do you typically get positive or negative comments? What is the feedback like?

Nick DiPaolo: It’s been good! You know, like I said, they get to see a little bit more of me, and I’m a little more political in this special than the stuff I did on Comedy Central, so people kind of take to that and they like that. I’m in “show biz” and I believe this kind of thing is refreshing for some people. So feedbacks are actually pretty positive.

TheCelebrityCafe.com: I know you’ve also done several half-hour specials on Comedy Central. Could you tell me a bit more about those?

Nick DiPaolo: The first one was way back in, like, the early 90s, I did something called Lounge Wizards. The only reason I bring that up is because they still rerun them. But that was kinda cool, it was my first time doing any television. It was a real showcase – a half-hour special as opposed to a 5-minute spot on An Evening at the Improv, or one of those cable shows. And then I did two shows on Comedy Central Presents over the last couple years or so. And those are great, because at the time I was on a show called Tough Crowd with Colin Quinn, which was pretty popular.

To do a half hour on television is a long time. Comics are used to doing a 5-minute spot on Letterman or 4 ½ minutes on The Tonight Show, so to have a network give you that much time is kind of a big deal. The actual DVD is about an hour long. The Showtime special is like 46 minutes; they take out things that they think are too edgy.

It's very weird how TV works. You can’t mention certain things if certain companies are owned by certain companies, so they take things out. So after all that’s said and done, on the “Raw Nerve” DVD, all that stuff will be put back, which will come out in a couple months, not sure. It’s about an hour when it’s put back. It feels good. When I’m headlining in a club somewhere, you do 45 minutes to an hour, so…it was fun. It was nice to be able to cut loose.

TheCelebrityCafe.com: That sounds really awesome. I’m aware that you’ve also performed on shows like The Tonight Show, Late Night with David Letterman, Conan O‘Brien, and others as well. What were some of those experiences like?

Nick DiPaolo: Those were great! All those guys are really nice. You always hear people bad-mouth them, but they were nothing but polite to me. My best spot was my first Letterman spot. Those are the 5-minute sets as far as television goes. That one was almost technically perfect. Then The Tonight Show was a big deal because of the name recognition back then. It was a big deal for me because I grew up watching Johnny Carson on The Tonight Show, and Jay Leno is from my neck of the woods: suburbs north of Boston. I grew up probably about 15 minutes from where Jay grew up. So it was nice to see Jay who’s a Boston guy doing so well. He put me on a couple times.

Conan was great too, he’s another Boston guy, and he couldn’t have been nicer. I did his show like 4 or 5 times. Same with David Letterman. My first time he had me sit on the panel and talk for a few minutes before the show ended. That’s a real thrill, ‘cause you grow up watching those guys. I remember seeing Letterman and Leno when they were actual stand up comedians.

TheCelebrityCafe.com: You’ve also written for The Chris Rock Show and were nominated for two Emmy Awards. That must feel pretty rewarding?

Nick DiPaolo: That was probably the most fun I’ve had as far as the show biz-related job. It was great. My buddy Louie C.K. got me the job; He was a writer there for a couple years before I got there. Chris saw me in a club and we started chattin’. It was actually a funny story: I was headlining a club in Pittsburgh. I’m on stage on a Friday night and the manager of the company comes up with a note that says to bring Chris Rock up on stage. So I’m like what’s he talkin’ about, I’m in Pittsburgh! And I look over and Chris Rock was in the corner. He was making a movie with Matt Damon or something. So we brought up Chris and then after the show he took me out to some strip club, haha. And we started chattin’.

I was living in LA at the time and he called and said, 'how’d you like to come back to New York and write for the show?' Which was perfect timing because I was getting sick of LA so…that’s how that’s done. And it was such fun. I mean, it was a great collective group of people, and we got along great. Chris Rock was just the greatest part. He’d come into the office on a beautiful summer day and say, 'Screw this, let’s go to the Yankee’s game!' Oh, what a great time that was. That was one of my highlights.

TheCelebrityCafe.com: That sounds like so much fun. I know that you also used to be a radio host on 92.3 Free FM in New York City 2007 when the station changed formats. How was that experience?

Nick DiPaolo: Ugh! I absolutely loved it. The problem was the station I was on was Howard Stern’s old station. It was right after he left and the station was hemorrhaging money, which I didn’t know when I took the job. I only ended up being on it for about six months and I loved it so much that I’m still trying to get back into radio. I mean, I love it as much as stand up. If you’re a comedian and you get your own radio gig, it’s great.

I loved it. I absolutely loved being able to be funny in a conversation without being heckled or having a bachelorette party, you know what I mean? It's great, it’s such a personal medium, having people sitting in the car listening to you. And they become real loyal if they like what you’re doing. So I still wanna get back on the radio, I like it as much as stand up.

TheCelebrityCafe.com: Speaking of radio, you also appeared on radio shows like Howard Stern. Any interesting times that stand out from being a former frequent guest?

Nick DiPaolo: Oh yeah! Howard’s always interesting because you never know who’s going to be on set. I remember the last time I was there, a guy from Jackass was there walking by with his butt hangin’ out, literally. You never know what you’re going to find when you go on Howard Stern.

One of the funny things...it was the second to last time I was there. I remember my wife was away for the week in France, I was home and made myself hard-boiled eggs. I took them out of the refrigerator and put them in the microwave for like a minute ‘cause I like them warmed up. Apparently a minute is too long. So when I took it out and bit into it, it exploded – literally exploded, like a firecracker. I’m telling you this because I had to do Howard Stern the next morning and my lip was burned. I had like a scab on my lip! And I remember getting there and the other guest was like, a really hot 23-year-old chick. And I’m sitting there with a scab on my lip and Howard’s making fun of me. I told the egg story and no one would believe me. They were like, ‘Oh that’s a cold sore!’ and I was like, 'Go home and put an egg in the microwave and you tell me what happens!' Oh man, it hurt like crazy. And of course Howard’s torturing me. That show’s so fun. You go on and you feel like you’re friends.

TheCelebrityCafe.com: Growing up, did you always know you wanted to be a comedian? Were you the 'class clown' of your schools? Or did you ever want to pursue something different?

Nick DiPaolo: I always kind of knew I wanted to do this. Even at like 12 or 13-years-old, like I said, I’d watch Johnny Carson’s monologues.

I remember my parents telling me to go to bed and I’d go up and watch from the stairs since the set was downstairs. There was something inside of me even when I was really young. And then I remember seeing Jay Leno on the Mike Griffith Show, which was really popular at the time. I also remember seeing Letterman on The Mike Douglass Show, so there was something I was attracted to. And my dad was very funny, too. There was this guy, a family friend, who that used to come over on Wednesday nights and he would make him laugh ‘til he would take his glasses off and would literally be crying.

All my fiends were really funny, too. I lived in a really cynical, funny town. My best friend was Bob Murphy, who graduated first in our class. And he was brutally funny, just a really smart, great kid. So it was all around me.

I saw Richard Pryor: Live in Concert a movie that came out when I was probably about 16. And that just floored me. There was just a lot of influence. Something attracted me. The Three Stooges, too! We used to watch everyday, you know, me and my brother, growing up. We loved it. So yeah, it was something inside me I think, even as a young kid.

TheCelebrityCafe.com: So it seems like it was kind of like fate that you would pursue this kind of profession, huh?

Nick DiPaolo: Absolutely. It was so comfortable. I had a couple of office jobs out of college. And I was a door-to-door salesman; you know, I wore the suit and took the subway into work into Boston. I tried that for a year, and I could just tell, since I spent half those jobs trying to make the people laugh. They were always telling me that I really ‘oughta try comedy, cause stand-up got really big when I got out of college around the mid-80s. So they were all like, 'Why don’t you go to the open mic night?' So eventually I did.

TheCelebrityCafe.com: Well, you know what they say, you gotta do what you love.

Nick DiPaolo: You do. It really is true. If it all ended tomorrow, I feel like I’d beat the system for 24 years, you know.

TheCelebrityCafe.com: You’ve already accomplished so much. What are your future goals, or anything you are currently working on?

Nick DiPaolo: I’d really like to get back on radio and have a popular radio show. It’s something I think I’m really good at. It’s such a tough market though because of all this technology, and MP3s, and podcasts. They sort of get caught with their pants down, and wasn’t ready for this. It’s a real mess. They’re afraid to hire someone who might take a few risks. It’s a hard time.

I don’t want to move to Cleveland to be a morning DJ, I wanna have a talk radio show where I could talk politics and be funny at the same time, maybe in a New York market somewhere. Or serious radio, which I’m kind of auditioning for right now. I’m doing “Howard 101” Monday nights from 7 to 8. I’ll do other stuff too, like my buddy Louie C.K. has his show Louie, so he calls me up time from time to time and I'll do some acting here and there.

But the radio thing, I like it more than TV and as much as stand up. So my goals are pretty modest. It’s to get back on the radio and to do stand up.



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