Kyle Dowling is a New York-based writer who’s been published in Penthouse, Playboy, The Smoking Jacket, The Believer and several other sites. He’s interviewed personalities like comedians Jimmy Pardo and Marc Maron and most recently, he spoke with one of the funniest, most un-PC comics in the biz (and sport talk show host) Nick DiPaolo. You might recognize Nick from his cameos on Louie, Opie & Anthony, Tough Crowd with Colin Quinn, The Dennis Miller Show or his various Roasts on Comedy Central. The comedy vet talked about his political bent, the power of radio, working with Artie Lange, Louis CK’s self-produced DVD & TV show, and much more.
KD: What made you get into comedy?
ND: I was always attracted to it, even as a kid. I remember watching the Mike Douglas Show and the Merv Griffin Show, and seeing Jay Leno on Merv Griffin. I was just amazed that a guy could come out and talk and have an audience laugh at him. I remember seeing David Letterman on the Mike Douglas Show. He said he had an unusual childhood. His dad used to tease him with power tools. Then he made a joke about the gap in his teeth—which was more pronounced then than it is now even—but he said his parents were going to fix the gap but they ended up spending the money on patio furniture. I also remember the Tonight Show monologues. My parents would send me to bed at ten or whatever and I’d get out of bed, open the crack of the door and look down the steps to watch Johnny Carson do his monologue. Something was attractive to me at a young age. It’s funny, I was reading about some other comic—I can’t remember who it was—but he said the exact same thing… watching the Tonight Show without his parents knowing. It’s kind of odd.
KD: But you didn’t start doing stand up until you were twenty-five or so. Why would you say it took a little longer for you to start? I know some comics start when they’re very young.
ND: Yeah, my buddy Louis C.K. did. Apparently I should have started at seventeen, the f*cking money he’s making. But I think you’re ready when you’re ready. My parents had a plan for me, you know? High school, college… so I kind of followed the rules but while I was doing that I was always a joker around my friends. I kept to myself mostly but around my friends I’d turn it on. I got out of college in ‘84, had a couple jobs, office jobs—suit and tie—and I ended up working for this marketing company. That was my last day job. It was like 1987/88. I was in my 20s. During the day I’d have like six guys in my office that were twice my age and I’d be doing impressions for them and making them laugh with the door locked, making fun of their wives and stuff. The boss would come in and go, “What the hell? You’re in DiPaolo’s office again?” And then stand up comedy started to boom right around then. In the Boston area it was outrageous. Every restaurant and pub had a comedy night, you know? I was living in Brighton at the time with my buddy and he kept pushing me for like a year to go to an open mic night. He stayed on me constantly to the point where we almost got into a fight one night; he was challenging my manhood as far as not going onstage, because he was so convinced that I could make a living doing this. I kind of believed it, too. I just didn’t have the balls. Then finally I caved in one day and went to an open mic.
KD: So you weren’t rooming with Louie then?
ND: No, that was about a year later, a year or two later. We came down to New York together. We had only been doing comedy a little, he had been doing it—like I said—a couple of years longer than me, but after about two years of one-nighters in Massachusetts we came. Really all over New England I should say… it was a glorious time. My manager at the time was Barry Katz, he booked about 80% of the rooms. I could show you my book—I worked over 300 nights my first full year, which is invaluable to comedians. I didn’t know it then but now I realize.
KD: You hear all of these stories of comedians driving incredibly long hours to make fifty dollars or so. Sometimes fourteen hours. I guess it’s all the drive for that craft.
ND: It is. It’s like anything else… once you look back on it you’re like, “What the f*ck was I thinking?” I never had to drive fourteen hours to do a gig. I was lucky because I was located in Boston. People were moving from other parts of the country to Boston to do comedy because it was such a flourishing scene. People like Janeane Garofalo moved to Boston, Bobcat Goldthwait, all these big names; Kevin Meany whose from White Plains. All these people came to Boston. It was the mecca to develop an act, you know? But the last few road gigs I did, which I don’t do know because of the radio show, I had an opening act. I introduced myself to him the first night and said, “Where are you coming from?” and he said Florida. I said, “What time did you flight land?” and he said, “I drove.”
KD: That’s crazy.
ND: Yeah, he drove from Florida to Michigan! And he was the feature act, the guy that goes on before the headliner! He couldn’t be making more than $500. Once I met another guy who was living out of his car when I first started. I flew out to the Midwest and I did a bunch of gigs where I had to rent a car. On one gig he picked me up and I said, “When was the last time you were home?” He said, “seven months ago.” He had all his clothes in the car; he had a cage with his cat in it. It was just so f*cking sad. I go “You know you don’t have to do it this way.” And he was pretty funny, too. Thor Ramsey was his name. I said, “You don’t have to do it this way. You can move to an actual city and get an apartment.”
KD: What was your act like when you first started? Is it at all similar to how it is now?
ND: You find your voice over the years, so it was similar as far as being really sardonic and sarcastic. It always had a rapid fire approach, four or five punches attached to every joke. That style I developed in Boston because the guys I was following were so God damn funny and they talked so fast. That part of it is similar, but the content itself? You mature. I think my act obviously got more socially relevant over the years but the style is the same.
KD: Was it that maturity that made you bring politics into your act?
ND: Yeah. When you’re single and running around New York City till five in the morning, getting drunk and chasing broads you have eight stories every time you wake up. Whether it’s getting chlamydia or getting caught cheating your life is much more interesting. Then you settle down as you get older and you turn the telescope outward or whatever. You start to say to yourself how did I get like this? And you start, you know, pointing at the environment and such. It’s funny, I wasn’t that political but as soon as I got to New York I started reading the Post and the New York Times and comparing the two points of view. I’m not real political but definitely much more than I was as a young comic.
KD: Do you think that the comedy world is shifted more left?
ND: Oh yeah. No doubt.
KD: Has that helped you or hurt you in the comedy world? I certainly think it’s helped you stand out?
ND: It might make you stand out but the powers that be—I mean if you consider stand up comedy part of show business, which it can be. It’s not as connected as everybody thinks. Like Artie Lange says, “We’re like the plumbers of show business,” which is true; we’re kind of like the blue-collar end of show business—but show business is run by lefties, ultra-lefties. They don’t care for people who think like I do and they really protect that too. I’ve probably made it harder on myself. I could have just kept my mouth shut, but what’s the point of getting onstage every night if you can’t speak your mind? You’re just going to be phony. My contemporaries say I could be a lot more famous if my political issues were quiet.
KD: But you wouldn’t be true to yourself then.
ND: Exactly, and I don’t know how that would read. It would probably come through as phony. But it’s such a double standard. With Tracey Morgan, the stuff he said about gay people a few months ago, if I ever uttered that I’d be kicked out of show business. There’s a lot of hypocrisy.
KD: It seems that no matter what side you’re on [left or right], the comedy world is an incredibly tight one filled with mutual respect that not many other professions can understand. It wouldn’t be the same if you guys were all janitors, but the fact that you’re comedians has a lot to do with it. It’s the craft of comedy that holds you together no matter what.
ND: Yeah, it really is true. I’ll give you an example of that. Janeane Garofalo—who I don’t know if you can consider a comedian anymore, she’s like a far left radical pundit— actually praised me about a year ago or a couple of years ago in an interview. I don’t know how my name came up but she said something about me being a comedic genius, even though I’m a Republican or something. And I don’t call myself a genius; I thought that was much. But when I heard it came out of her mouth I think it proves what you’re saying is true. It is an odd way to make a living and not everybody can do it.
KD: I think it takes a lot of balls.
ND: Yeah it does. Which is why girls are not that funny. No I’m kidding. Jerry Lewis said that in an interview. But yeah, you have a certain respect because it’s a unique thing.
KD: You’re very confident on stage. You have a real presence with that a rapid-fire approach. When you go to different parts of the country do you find yourself changings parts of the act at all, perhaps to appeal more to different parts politically or socially? Or is it ‘this is me, take it or leave it’?
ND: You don’t adjust to the audience ever. If you did that over the years you’d stand for nothing. You wouldn’t have a point of view anymore. It could take a month before a joke works right so you can’t just tweak it for a different city. You’d end up just vanilla you know? But believe me, what flies in Boston flies in Houston. Maybe you might have to talk a little slower in some places but they get it, especially sarcasm. To me I found that was the universal thing. I don’t care where you are. People love that.
KD: How did you make the transition into radio?
ND: When you make your living on the road doing stand up as a headliner part of your job is that they wake you up at six in the morning and have you do radio stations to plug your gigs. They wake you up, it’s ten degrees out and they drive you around to like four different stations. Then you walk into a morning zoo thing and try to be funny.
KD: At 6AM?
ND: Yeah, and it’s horrible.
KD: It sounds horrible.
ND: It’s f*cking horrrrrible. It’s the worst part of being a comedian; you can ask any comedian. But I started to get good at it, as much as I hated it. I was doing a gig in Minneapolis, Acme Comedy Club, which is still my favorite club in the country, and this guy happened to be a huge fan of mine. He put me on and let me stay there all morning, and by the time I got back to the hotel to go back to bed the club called and said all four shows had sold out.
KD: Wow. Just because of the radio show?
ND: Yeah. He left me on all morning and I was just on fire. A bell went off in my head of how powerful radio is. I was like, ‘Oh that’s how it works.’ So that really piqued my interest.
KD: What year was that?
ND: That was, I want to say 10/12 years ago.
KD: And ever since then you’ve been consumed in the power of radio.
ND: Yeah. Then I did Howard Stern. Howard saw me on The Tonight Show. I was living in LA at the time and Howard couldn’t sleep one night back in New York so he was watching the Tonight Show. I’m in LA sleeping and my phone rings at like five in the morning and it’s a friend of mine in Miami. He goes, “I’m listening to Stern and he’s talking about you right now.” So I get up, I’m half asleep but I call the Howard Stern Show. Gary Dell’Abate answers and I say I’m the guy Howard was talking about a few minutes ago. So they put me on hold for like a half hour and then sure enough Howard put me on. He was really nice to me and says, “Yeah, so look when you come back to New York come see us.” And a month later I happened to be in New York and I try to get on and they’re like, “Nah.”
ND: Yeah, they had like Schwarzenegger on or somebody really famous. For the whole week I couldn’t get in.
KD: So how long did it take you to get on there?
ND: After that probably another year.
KD: That long?
ND: I think so. I think it was that long.
KD: Is that where you met Artie Lange?
ND: I met Artie in LA, when I was living in LA, at an audition. He had some pilot for a sitcom—Mr. New York or something; whatever—he was the lead and I went in to read for some character for the show. I didn’t know Artie but he said he was a big fan and that’s where I met him originally. Then when I started going on Stern that’s where I started to see more of him. And then we did gigs together. We had an immediate like and respect for each other.
KD: That’s great. And how did The Nick & Artie Show come about?
ND: Well I got a radio show on my own; it was on Free FM-KROK in 2007 from December to May. When that ended I figured I’d get right back on radio. But trying to get your own radio show in the New York City market? That’s like trying to get a TV show. It’s really, really difficult. I had no idea. So here we are four years later and I finally get back. But in the meantime I filled in for people every chance I could. I thought I was going to be a funny Rush Limbaugh type. I filled in for Jerry Doyle, some of these right wing guys.
KD: And Dennis Miller’s show too?
ND: I did, which was great. I sat in for Dan Patrick a couple of times; they really liked what I did. Any chance I got I filled in. My old agent hooked me up with this guy Chris Crane at Direct TV. He was a fan of mine from the show Tough Crowd and heard my demo at Free FM. He had a lot of faith in me. I filled in for a guy named Tony Bruno like three or four times, a Philly sports guy with a nationally syndicated sports show, like over 200 markets. I actually sat in at WABC a couple of times. I went up to Boston last year around this time and did a week at WTKK. I thought for sure I was going to get that because I’m a Bostonian, but the woman thought I was too politically incorrect and she was afraid of me. Blah, blah, blah. But finally Tony Bruno retired or went back to Philly so there was an opening. Chris Crane said, “We’re gonna put you in Tony Bruno’s spot. You’ll automatically have 220 affiliate stations.” That fell through at the last minute so we had to go from market to market one at a time, but they asked, “Who would you like to work with?” They mentioned Tony Siragusa. I’m like, “eh, too Italian.” And he wasn’t interested in me either. And then—honest to God, Kyle—I’m sitting there and the phone rings and I look at my phone and it says Artie Lange. I hadn’t heard from Artie in about a year.
KD: Oh really?
ND: Yeah, so I go to Artie, “Hey, how’d you like to do a sports talk radio show?” He’s like, “Well, yeah!” So that’s how it was born. I called the guys at Direct TV, and of course the head honcho is from Long Island and was a huge Stern and Artie fan, so he was thrilled. These guys at Direct TV are great. They say what they’re gonna do and just do it. They’re big fans of both me and Artie and that’s really how it happened.
KD: That’s very cool. This is really his first thing after getting clean, no?
KD: That’s weird that one phone call really changed everything.
ND: It’s pretty crazy, you know? I said this on Kimmel. Michael Vick gets a second chance? Artie wasn’t machine gunning puppies and putting f*cking Chihuahuas in toaster ovens. Why shouldn’t Artie get a second chance? It benefits both of us. I get his name recognition and he needed a job and money. We do everything 50/50.
KD: It really is a very funny show. It’s a sports radio show but the interesting thing to me is that you have athletes come on, but you also have comedians and musicians. Was that your goal?
ND: Yes, but I still don’t think we’ve made that clear enough to people. The reason we said sports is because of Tony Bruno. He had 250 markets cut out for us, sports markets. So it’s kind of putting a square peg in a round hole. I’m not a sports guy but I do know enough about it where I can fake it, same with Artie. We’re not going to do X’s and O’s. It’s ten o’clock at night. At ten o’clock at night you can talk about anything. The Jets and Giants game will have been analyzed four hundred times. So we said it’s from a fans point of view. We’re not experts. If you want to talk X’s and O’s, call up ESPN.
KD: I think that’s a great approach to it.
ND: It is. It’s a nice little niche. We’re not obligated to open with a sports story. Eventually who knows what it’ll turn into but we did that because like I said, those were the markets that were open. But we do love sports, so it is from fans point of view.
KD: I listen to the show as a podcast and I’m the farthest thing from a sports guy but I love the show.
ND: Oh that’s great to hear. That’s exactly what we want to hear. Twenty years ago I loved sports. Now I’m bored to tears with it all, except for college football. The NFL is just dog sh*t, so watered down and there’s so much parody. The f*cking athletes are clowns. They’re Twittering during the game, but the beauty of talking sports on the radio is that it’s a microcosm of our society. It contains stories about race, gender, politics. Everything’s incorporated and sports is an easy way to get into those subjects. I’m very opinionated about politics but nobody ever wants to hear it, so sports is a fun way to get into it, you know? So it’s kind of a good lubrication.
KD: That’s an interesting take on it. I’ve never heard that. How do you guys go into the show? You have a bullet list of topics you want to hit?
ND: Basically. I’ll read a couple of newspapers. I’ll watch SportsCenter. I’ll listen to Mike Francesa on the way into work. I’ll go on ESPN.com and read those stories. And that’s really about it. Then I go onto the non-sports stories and read whatever it is that’s going on in show biz. But we have a couple of producers and they have ideas; they do their homework too. I get to the studio a couple of hours before the show starts and we go over the stories and try to make a lineup. We’ll try to put some stories in order. Then me and Artie will get on the air and I’ll say, “What about this trade the Phillies made,” and Artie will go into some ten minute story about a time he was in Philly and got drunk and woke up on a park bench. Then I have to figure out a way to get back to the f*cking story we were talking about.
KD: You guys have such a good chemistry.
ND: Artie is the greatest storyteller of all time, and I can be quick. I can embellish those stories. I’m funny conversationally, which is a blessing on the radio. It really is a good chemistry. He can tell a good long-form story and I can make a joke out of anything whether it’s a collar or talking about a specific story. I can convert something into a joke in nanoseconds.
KD: I would imagine that would help immensely onstage as well.
ND: Yeah, that’s where you develop it. That should be where you start as a comedian. If you don’t have that ability to be funny off the cuff you really shouldn’t be doing comedy, at least stand up I don’t think. That’s the foundation to me. Then you learn how to write material and develop jokes. When you’re doing an act and some nights your jokes aren’t flying it doesn’t hurt to have a little personality and quick wit. You can save yourself on many nights. And then the nights when your jokes are killing and you add stuff in between off the cuff, those are the nights where you blow the roof off the place.
KD: So because the show is on Monday through Friday from 10PM to 1AM is it harder to get on the road now?
ND: It’s impossible, and not only the road. In order to be good at stand up you have to do it every night. You have to be in the club every night working on material. You don’t just put an hour together in a week. The last special I put out? That was two years in the making. And that’s every night of being on stage, tweaking this and that. Louis CK is a perfect example right now. This is what he concentrates on. You have to. It’s a muscle. I
remember Jay Leno saying that. It’s like a muscle; it atrophies if you don’t use it. And this is a little concern of mine because of our hours, 10PM to 1AM. And like I said I get there a couple of hours early, so my job is like 8PM–1AM every night. Those are the prime hours of a comedy club. But me and Artie plan on doing theaters if things go right.
KD: After doing this for twenty something years you have to be itching from not doing it.
ND: Yes and no. After twenty-five years I was looking for some sort of break, some regular hours. You can only go to Milwaukee so many times. But the last couple of nights I’ve been getting a little bit of an itch and missing it. Also reading about my buddy Louie, my old roommate, and how he’s the king of the hill right now. I’m so proud of this kid. Nobody deserves it more. He’s that talented and that funny, but a part of me is jealous that he’s out there—king of the hill—but I couldn’t be happier for him.
KD: Yeah I got his $5 stand up DVD.
ND: Did you watch it yet?
KD: I did.
ND: How was it?
KD: Oh it’s hilarious. It’s really very funny.
ND: He puts the work in, you know? I don’t know how he does it. He’s got two little girls he takes care of. He’s got his FX show. This guy is so efficient with his time. He’s brilliant. I mean the show that’s on FX, he edits that sh*t on his laptop like it’s nothing.
KD: Yeah, like a 13-inch MacBook pro.
ND: He’s just a f*ckin’ genius, this kid.
KD: Well you know what’s funny; he sent an e-mail out to the people who got it, thanking them and such. And he explained in detail the amount of money that was made. He went on to say he planned on doing it again unless he was given a huge offer from one of the big guys. He was very honest; it was great.
ND: Yeah but did you read the latest? My web guy sent me the latest link today. As far as the fact that it was less than he got paid by the big guys, that’s not true anymore.
ND: No, he net a million dollars.
KD: Jesus Christ.
ND: He net a million dollars! NET a million dollars. And trust me I know HBO and Showtime and it isn’t sh*t. They rip you off. Somebody wrote a review saying they were surprised this [Raw Nerve] was Nick Di Paolo’s first DVD. I e-mailed the guy saying if you knew the work that goes into versus the monetary payoff you’d understand.
KD: Oh yeah I bet.
ND: But with Louie, this is the way of the future. My web guy, to be honest with you, he was preaching this stuff to me five years ago. But it has to do with the level of fame. I mean to have a hit show on TV on FX, that makes everything else a lot easier.
KD: I would imagine because of the Nick and Artie Show and all of your appearances elsewhere, when you do find time to do stand up your shows would be doing rather well.
ND: Well you’d be surprised. We don’t have a market right now in New York. We’re not on a local market. Doing the O&A and Howard, that helped a little bit. As far as Artie being a regular on a show like Howard, that’s when you get people to come out and see you. Or if you have a hit TV show like Louie does. It takes a lot to become a draw.
KD: That’s definitely true. But the radio show just started back in October right? So it’s really in its infant stage.
ND: Yes it is. Eventually the plan is for us to be on Direct TV by March. It’ll be our radio show on Direct TV. These guys are so high on the show and so believe in me and Artie. A couple of weeks ago they were searching for a place to build a studio, like a man cave. They are very hot on the show. Right now it’s not a money-making venture for Direct TV. They’re probably losing money but they plan on this thing on being pretty popular.
KD: The new space will be here in the city?
ND: Oh yeah. Yeah. They were looking at places in Tribeca and such. We already looked at a couple of spots but one of them wasn’t handicapped accessible. All these f*cking government rules—it’s the reason I vote republican. All these stupid rules that keep people from doing business. But that’s the goal.
KD: What would you say you like best about doing the show?
ND: I look forward to hanging out with Artie. I’ve been a stand up comedian for twenty-something years and have become very jaded. Anybody that does this for a living will tell you that you don’t laugh anymore. It takes a lot to make you laugh, and there’s about five people in the world that can make me belly laugh. Artie is one of them. I didn’t know how funny Artie was. I knew he was funny but I didn’t know just how God damn funny
he is and what a great mind he has until I started working with him every night. He makes me belly laugh and I make him belly laugh. I really look forward to going to work.
KD: When you listen to the show it sounds like you’re sitting down riffing with your friends.
ND: Yeah! That’s exactly the picture we want to paint.
KD: I certainly think you are. And like I said I’m not a huge sports guy but the show is incredibly entertaining. It sounds like two guys sitting down having a funny conversation.
ND: And that’s exactly what good radio is in my book. There has to be chemistry there. When we did the test show back in the summer, July or August, it was immediate that we had that. Some high up executive at Clear Channel—like the second to highest guy—heard it and he said to the Direct TV guys, “Don’t walk to sign these guy, run,” or something like that.
KD: That’s great.
ND: But sometimes you listen to two guys on a radio show who have been together for twenty years and year can tell they just hate each other. But that could happen to me and Artie. Who the hell knows? It might be like a marriage if we spent enough time next to each other. But we genuinely respect each other. And like I said that guy just makes me laugh. He had me laughing off air a couple of days ago. He said something that was mildly amusing but the way he said it, I just took the whole picture in. Him in his t-shirt, scratching his belly, I couldn’t stop laughing. I had to leave the room.
KD: Of all of the things you’ve done, what is your greatest moment in your career?
ND: I’m not sure if it’s my greatest but I was doing some sh*tty club—I think it was in the Poconos—and I got a standing ovation after doing like an hour and a half. And half of it was off the top of my head. Nobody sees those nights you know? The Showtime special, I’m very proud of. My first Letterman or first Tonight Show, those are nice memories. But those nights where you make a crowd actually stand up? There’s never any cameras around, no body ever sees it. It just sort of dissipates into thin air. But also the Young Comedians special on HBO, I’d have to say that’s still my biggest thrill because they only picked five people to do it out of the whole country. It was a big thing. If you look at the line up—Ray Romano was on that show, Janeane Garofalo did movies after. Ray became so successful. Judd Apatow—maybe more successful then all of them. Then it’s me and Andy Kindler fighting for laughs. I think the HBO Young Comedians special; I’d put that one up there.
Also, one of my favorite memories in show business is doing an episode of The Sopranos. I played a cop, had a couple of lines. But I have to put that in there because in my opinion that show is one of the best in the history of television.
KD: Well thank you this was great. I’m a big fan and have Raw Nerve… incredibly funny.
ND: Thank you. I appreciate it, Kyle.