Playboy asks Kevin Connolly 20 Questions As Only Playboy Can!

Q 1

PLAYBOY: The TV graveyard is full of canceled series about the inner workings of show business, yet Entourage thrives. TheWashington Post called you and the other boys from Queens “deplorable, unpardonable, shameful—and why can’t you and I be just like them?" What makes this show work when others have failed?

Kevin Connolly: It’s the friendship thing between guys. People across the country may not get Hollywood’s inner workings, but they do understand how guys relate to one another. Often some dude on the street will shout out that his buddies call him the Drama or E of their group. Entourage can be a guilty pleasure; it’s easy to watch.

Q 2

PLAYBOY: If viewers like the characters, would they also like the guys who play them? How much is TV imitating life?

Kevin Connolly: There’s a lot of ballbusting. Fuhgedaboudit. We all di out. In real life Jeremy Piven is that fast-talking guy—get into a verbal battle with him and you’ll go down in flames, guaranteed. That whole life-imitating-art thing is trickiest for Adrian Grenier. He’s an actor playing an actor, so people often want him to be Vince, but he’s not. He’s Adrian. Kevin Dillon’s a sick lunatic for golf, always talking smack and practicing his swings. Jerry Ferrara is the least like his character—he’s a supersmart dude who is not a stoner slacker. Personally, I wouldn’t stand for some of the abuse E, my character, takes from Ari, played by Jeremy. We’re all slightly darker versions of our characters.

Q 3

PLAYBOY: You’re Vince’s wingman on the show, and you’re really good at it. What about off camera?

Kevin Connolly: Adrian and I are good wingmen for each other. When we were shooting the Cannes episode, we wrapped work one day and just took off in our wardrobe. We knew we would be in if anything happened to the clothes, because we had to wear them for the next day’s shoot. We took off anyway: It was Cannes, and guys got to do what guys got to do. We had to monitor each other’s drinks and make sure no one spilled any red wine, or worse.

Q 4

PLAYBOY: What makes a good wingman?

Kevin Connolly: Every single guy needs an ace wingman. He’s indispensable and independent, somebody you can trust to go with to a bar or club. He’s got to be on equal ground with you in a social situation, carry his own weight, talk to girls and be able to look after himself. I also have myself covered with bicoastal wingmen.

Q 5

PLAYBOY: If we’re to believe TMZ, you’re out on the town every night. What is your typical evening like?

Kevin Connolly: tails and dinner first, then I’m like everyone else: I go to clubs and chase girls. The best thing about L.A. is they throw you out at two A.M., so you can wake up the next day, feel like a human being and get to work with less damage. Back East, you’re out having a good time, you blink, and it’s four in the morning. No good comes between two and four.

 Q6

PLAYBOY: For a long time you and Nicky Hilton were a couple. What happens when you see her now?

Kevin Connolly: Here’s what I always respected about Nicky: Before Entourage I was living in a one-bedroom apartment—a broke kid from Long Island—and we got together when I had nothing to offer her. We’re still friends, and we still hang in the same circles. But the paparazzi aren’t hanging out in front of my house anymore. When I was dating Nicky one thing I said was, “Nothing’s worse than being chased by paparazzi who aren’t trying to take a picture of you.”

Q 7

PLAYBOY: Does a hit TV show make your dating life easier?

Kevin Connolly: It can be both easier and more complicated. I met an attorney, about my age, and I was thinking, Okay, this girl is hot. We were out for dinner, and almost the first words out of her mouth were “I haven’t seen your show. I hope that’s not a problem.” Then over dinner she called me Eric three times. The first time I thought I was hearing things. The second time she definitely called me Eric. The third time I had to set her straight: “Oh, by the way, my name’s Kevin.” I showed her my license. “So you’ve never seen the show? I play a character named Eric onEntourage, which is an odd coincidence.” It was a weird way for her to start a date. It was a disaster.

Q 8

PLAYBOY: You’re using your Entourage cash to create the perfect bachelor pad. If MTV’s Cribs dropped by, what would we see?

Kevin Connolly: My father would be turning over in his grave if he saw me obsessing over fabrics. But it’s my first place, and I love being involved. First, I’m a big sports guy, so I’ve got the big couch, and nothing makes me happier than to come home, plop myself down and watch the Yankees on the biggest HDTV I can get on that wall. Then I have a nice little bar, classy, with high stools, so I’ve got the guy hangout done right.

Q 9

PLAYBOY: We’re guessing your life has changed since your childhood on Long Island.

Kevin Connolly: I had a painfully normal life. My mother was a waitress, and my father was a truck driver. He was an iron man who never called in sick and gave me my work ethic. My brother, Tim, a local detective who has done tons of suspect interrogations, told me he learned you get more with honey than you do with vinegar. I try to apply that in Hollywood. Swearing and screaming may work for Ari Gold, but it doesn’t always work for others.

Q 10

PLAYBOY: Rocky V, your first movie, was nominated for a Razzie Award for worst picture in 1991. Do you have any regrets about appearing in a famous flop?

Kevin Connolly: When I was growing up, Rocky movies were it, and when I got that role it was the greatest day of my young life. I was doing scenes with Rocky, the ultimate working-class hero. Sly was a big star by then, our great action hero, and even though people may diss the movie, it left one special impression on me. Hey, we weren’t running to art-house theaters to see indie movies out in Medford. You went to see Rocky, Rambo and Die Hard.

Q 11

PLAYBOY: You’ve directed a short film, Whatever We Do, that stars such heavyweights as Robert Downey Jr. and Tim Roth. Was it scary to work with actors of that caliber?

Kevin Connolly: They made me want to quit acting. I’m serious. With Tim and Robert I was rendered speechless by how talented they were. It just came out of them naturally. I went home depressed, thinking, Wow, maybe I should just throw in the towel.

Q 12

PLAYBOY: You skipped college, moved to L.A. and lived with a bunch of underemployed actors. But not all of them were underemployed for long.

Kevin Connolly: We had our own fraternity, doing our fair share of a whole lot of nothing, hanging in our actors’ flophouse in the Valley with the same actor guys I hang with now: Tobey Maguire, Leonardo DiCaprio, Lukas Haas and Ethan Suplee. We lived on cheap pizza and pasta—a house of out-of-work actors trying to take care of one another. Leo was the first in our group to pop—more like explode—with an Oscar nomination at 19. Just when I thought life couldn’t get any weirder, I walked into Tobey’s trailer and he was wearing the Spidey suit.

Q 13

PLAYBOY: Was it discouraging when they made it and you didn’t?

Kevin Connolly: Everybody here is chasing the same nickel. My career wasn’t so fast-rising—I’m 34, and I’ve been acting for 28 years. The thing is, you get to a point where you don’t know how to do anything else. But every time I was getting to the end of my rope, I got a little taste to keep me going. When the Entouragepilot happened, you would never have anticipated in a billion years it would become what it has. So it was like, Okay, cool, it keeps the ball rolling, and you make a little money to carry you through till the next job.

Q 14

PLAYBOY: Rejection can’t be fun. How did you deal with it?

Kevin Connolly: Rejection was my middle name for many years. It still is. Unless you’re Brad Pitt or Matt Damon they always want somebody else. Even those guys will tell you they’ve been through it. It’s humbling. Some people get lucky. I know a million great actors—guys who are 10 times the actor I am—who just don’t get breaks.

Q 15

PLAYBOY: No one on TV endures more short jokes than you. Just how tall are you?

Kevin Connolly: For the record, five-foot-seven. Piven isn’t much taller than I am. Entourage’s creator, Doug Ellin, loves the banter between Ari and E, and he said, “I need to abuse your character.” So there have been get-me’s from Ari about E’s height. Doug knows I don’t care. Just take us to the promised land, dude.

Q 16

PLAYBOY: The Ari Gold character has some great lines, like “Tell Drama he’s on the top of my list of things to do today, along with inserting needles in my .” Why do people love to hate Ari?

Kevin Connolly: He reflects our inner Ari. People like to think they have that somewhere inside—a bite-your-headoff kind of thing they can release at any point. That’s what I feel about the big producers like Ron Meyer, Jerry Bruckheimer and Brian Grazer, guys who can do a movie about whatever they want. Awesome. I’d love to release my inner big-shot producer, wield that power one day, play with the cinematic big toys and blow something up.

Q!17  

PLAYBOY: Tell us the truth: How often do you guys clash on the set?

Kevin Connolly: We spend massive amounts of time together during the season. Sometimes it’s 10 hours a day in a car—Adrian and Jerry in the front, Kevin and I in the backseat—staring at one another while being driven around L.A. on a flatbed. Like brothers, you sometimes get pissed. When someone’s having a bad day, you just back the off. But when the show’s over, we all go do our thing. Kevin is married with a baby and has a house in Malibu. Jerry goes back to New York. I dream about chasing that hundred-million-dollar movie to direct.

Q 18

PLAYBOY: Nonactor A-list celebrities have been guests on the show. How well do they act?

Kevin Connolly: Kanye West is a massive personality, but there he was hanging out, soft-spoken, down-to-earth. I was impressed to see Kanye step out of his comfort zone, work on his lines and act. It’s amazing to see big names—like James Cameron, who directed the biggest movie ever—come on because they’re fans of the show. M. Night Shyamalan, one of the coolest directors around, was just excited to be there. It’s funny: All the directors seem to be happy to be on a set and not directing.

Q 19

PLAYBOY: How much of Entourage is based on real-life Hollywood stories?

Kevin Connolly: A lot of plotlines are loosely based on Hollywood mythology you hear about. Martin Landau played a classic oldtime producer, like Bob Evans, who is part of that mythology. Our producer had a film teacher who always said, “Is that something you might be interested in?” Landau said that, and it has become an oft-quoted line fromEntourage. It’s also interesting how the show has created this life off the set for us that is now feeding back into the show—like using two of my real-life pals, Lukas and Ethan, guys I’ve worked with before who are now going to be my clients on Entourage.

Q 20

PLAYBOY: At the end of last season the Entourage troupe is in the financial crapper, downgrading from a multimillion-dollar mansion to living out of Drama’s condo. It’s all good in this season, right?

Kevin Connolly: We’re back from Cannes, dealing with the Medellin movie being unsuccessful and how that impacts Vince’s career and our lives. But then there’s a switch: Vince is broke, but with E’s expanding personal-management business the tide has turned. There’s money coming in, and now I’m starting to write the checks. But the guys are sticking together, and Vince will be back.