Entourage’s savvy wingman lives the ultimate Hollywood life. Who else hangs out with Leonardo DiCaprio and Tobey Maguire, dated Nicky Hilton and directed Robert Downey Jr. It sounds like a certain TV show, doesn’t it?
Q1 Playboy: The TV graveyard is full of canceled series about the inner workings of show business, yet Entourage thrives. The Washington 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.
Q2 Playboy: If viewers like the characters, would they also like the guys who play them? How much is TV imitating life?
Connolly: There’s a lot of ballbusting. Fuhgedaboudit. We all dish it 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.
Q3 Playboy: You’re Vince’s wingman on the show, and you’re really good at it. What about off camera?
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 shit 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.
Read the full 20Q interview at Playboy Interview
