Catching Up With the Stars of a Little Movie Called Entourage

Reunited, and it feels so…familiar.

The PA says there’s no parking available at the location, so I ditch my car in a lot on Sunset, and hop in a waiting shuttle. “They don’t make it easy on you,” I say to the driver as he wends the oversized van up the tiny streets above the Strip, stopping to perform K-turns at nearly every switchback.

The climb seems on message. At once inaccessible, cliché, and ideal, the Hollywood Hills are forever emblematic of a certain kind of ambition and success. When you reach the top, you’ve reached the top.

When we reach the top, there’s a giant, white, ’80s mansion perched over an infinity pool—and the entire city. Out front is a black 1965 Lincoln Continental Convertible, its top down. A camera drone hovers over its monolithic length as an actor struts out of the house, take after take, getting into the car, starting it up, revving the engine, and checking his look in the rear view mirror. This must be the place.

For a certain type of aspirationally oriented guy during the turn of the 21st century, there was no better exemplar of the pleasures of Hollywood material culture—and the male bonding that underpins and affords it—than the eight seasons of the HBO bromantic comedy-drama, Entourage. “For me,” series creator Doug Ellin says, “Entourage was always about—you know, there was the toys and all the trappings and everything. But at the end of the day, it was about friendship.”

Now, four years after the series ended, Ellin has reunited the entire gang—Vincent Chase (Adrian Grenier), Johnny “Drama” Chase (Kevin Dillon), Eric “E” Murphy (Kevin Connolly), Salvatore “Turtle” Assante (Jerry Ferrara), and Ari Gold (Jeremy Piven)—for an Entourage movie, which will follow up immediately where the series left off, and will open in theaters on June 3rd. 

We are on set for the filming of a promotion, itself aspirationally twinged, that connects Kevin Dillon’s character, Johnny Drama, to famed blended Scotch whisky brand, Johnnie Walker. One hour from wrap time, the shoot is two hours behind schedule. At least forty people crowd the house, clutching equipment and standing over monitors, sweating. Kevin Dillon bounds out of a downstairs bedroom, wearing a pair of brightly colored boxer shorts, and nearly crashes into us. We agree to hold our questions until they wrap.

The guys are all of one mind when I ask what it was like to get the gang back together after a four-year hiatus. “We didn’t miss a beat,” Ellin says. “It’s surprisingly easy to do, for some reason,” Dillon says. “It’s like putting on an old shoe—still fits great.”

Connolly extrapolates a bit further. “We actually started shooting the movie eighteen months ago. So, right off the bat, you cut that four years in half,” he says. “And we were meeting with Doug about the script before that, so it never really went away altogether.” He adds, “It wasn’t that different from an extended hiatus between seasons.”

Despite the perceived length of the gap or the ease of their transition, the world changed significantly during the course of the show and since its terminus. We moved from the go-go years of the economic bubble, to the tough years of the economic collapse, to the Piketty years of consciousness against rising income inequality. I ask if the aspirational tone has changed for the Entourage film, for 2015.

“I don’t think it has,” Dillon says. “Toward the end of [the series] the country was already going through a little bit of a recession, so we went away from the Hummers and stuff. All of a sudden certain characters were driving Priuses. But, coming into this movie, it’s right back where we left off. Giant yachts and jets, and all the good toys.”

Has Entourage changed your life? “I had Rob Gronkowski and Russell Wilson giving me medical advice on how to take care of a banged-up leg,” says Connolly.

Connolly makes it more personal. “I’ve been acting since 1980, and I didn’t get Entourage until 2003. I kicked around for a lot of years and got by by the skin of my teeth, survived some pretty tough economic times. For all the guys, we were fortunate enough to be employed during the recession,” he says. “But because of the nature of the show—it’s a wish fulfillment show, it’s a feel-good show—we never really wanted to touch on the hard times people seemed to be having. We wanted to give them an escape from that. So, in the Entourage world, there’s no such thing as a bad economy.”

There is such a thing as bad luck, however. Shortly after filming started, Kevin Connolly had an accident. During a big football scene, with all sorts of well known sport and movie stars lined up for cameos, Connolly received a pass from Seattle Seahawks quarterback Russell Wilson, was tackled by “Turtle,” and ended up limping off the field. “I broke my leg in two places,” Connolly says. “I got off the set and everyone thought I was going to kind of walk it off. And then somebody told Doug [Ellin], Yeah, I just went upstairs and Russell Wilson is icing Kevin’s leg and making him elevate it and telling him what to do.” He laughs. “I had Rob Gronkowski and Russell Wilson giving me medical advice on how to take care of a banged-up leg. Who better than a couple Super Bowl champions?”

Dillon commiserates. “We had to shoot around him a little bit. But, you know, if you’re gonna’ break your leg, why not have Russell Wilson throw you a pass. It’s a good story at least. Unlike my story. I just broke my wrist. I was skating with my daughter. I was on figure skates, I wasn’t even playing hockey or anything.”

Having missed each other when apart, and suffered when together, I wonder if the guys are looking forward to continuing with Entourage after this movie. “I think that the longer you go into doing a show, the easier it becomes. It’s no longer about, Would my character do that? Would he not do that? What would he say? You know what he would do and what he would say.”

Connolly takes things one step further. “I’d like to turn this into the Fast and Furious series,” he says. “I’d love nothing more than to do Entourage 6: Tokyo Drift. So long as we can keep it going, I’m in.”