HBO's Boys of Summer

The hit show "Entourage" enters its sixth season in 2009 with more stories of male bonding and outrageous fun.

(continued from page 1)

Over the first five seasons, the winds of Vince's fortune buffet the other characters—even as they try to create careers for themselves. As Vince's best friend, Eric starts out as the one person Vince could trust, becomes Vince's manager (much to the consternation of Vince's agent, Ari) and now has spread his wings to become a talent manager with other clients as well.

"I'd like to see him climb more of the corporate ladder," Connolly, 35, says of his character. "They should have him be a true player. E gets pushed around, but he's also done good stuff that he didn't get credit for. In 10 years, I hope he's running a studio."

Turtle is the guy with the hook-up, whether it's for a sponsorship deal that allows him to throw Vince a lavish party or a way for Johnny Drama to get a prescription for medicinal marijuana. But he tires of being the guy without a real job, beyond Vince's gofer. Though Turtle tries managing a rapper briefly—and works for a single day as Johnny Drama's personal assistant—Ferrara wishes they'd give Turtle a real career to dive into.

"I'd like to see him get some kind of a business of his own," Ferrara says. "I'd like to hear more of his back story. Although I do envy Turtle his laziness: I can't be that lazy."

Both Ferrara and Connolly refer to "Entourage" as a rarity: a show that worked right from the start and keeps on working, building popularity while maintaining quality over several seasons.

"I've been acting a long time and lightning strikes so rarely," Connolly says. "Nobody in his wildest imagination expected this kind of success. I guess the timing was right."

"It just snuck up on us," Ferrara adds. "One day we woke up and people were actually watching this show."

Says HBO's Lombardo, "It was a show that didn't grab everybody the first season. But by the second year, we knew we had a hit."

Connolly recalls the moment he realized just how popular the show was: "Jerry and I were at a game at Yankee Stadium—and they put me up on the scoreboard and played the theme song ["Superhero" by Jane's Addiction]. Jerry and I are diehard Yankee fans; we practically grew up there. And to be walking through the stadium and be recognized and cheered…"

For Kevin Dillon, 43, the success has been particularly savory. Like his character, Johnny Drama, Dillon has a famous (in his case, older) sibling: actor Matt Dillon, who got his start as a teen. Dillon followed in his brother's footsteps, landing roles in such films as Platoon and The Doors. Though he was a steadily working actor, he hadn't found a role that gave him the kind of visibility and credibility that "Entourage" has.

"This show turned my career around," Dillon says. "Any success I've had in the past, this has doubled it. But you know, I had a gut instinct from the pilot that they would pick up the show and it would run."

Like Dillon, the character of Johnny Drama finds a surprising second act to his run at stardom: "Drama's kind of got a hot career right now. I thought he'd struggle throughout the series. He's got so many dimensions; he's got a big heart and he's a good guy in a lot of ways. But he's also got issues and character flaws and that's what makes it fun to play. He's the only character on the show who hasn't really had a relationship—but I don't know if relationships are funny. I like him being funny, crazy—totally unpredictable at all times."

Having wrapped at the golf course, the production moves locations—from City of Industry farther east, to Auto Club Speedway in Fontana, near San Bernardino. The sun is playing hide and seek with the clouds, but the day is comfortably warm.

The massive track, with its mile-long stands, is deserted except for the "Entourage" crew and a few racetrack staff. This will be a scene from the season's fifth episode, in which, for Turtle's birthday, Vince treats Turtle and the boys to an afternoon roaring around a banked racetrack in Ferraris that hit 140 mph without breaking a sweat.

On this day, they'll film the post-driving moment: the amped-up pals, basking in the afterglow of a high-speed adventure. At which point, Vince will hand Turtle the keys to one of the Ferraris and say, "Happy birthday, Turtle."

The next day, the actors will suit up, jump into the gleaming sports cars and shoot behind-the-wheel sequences (at a much more manageable 65 mph). In preparation, the four spent part of the previous weekend being trained in high-speed driving in the same Ferraris.

"I loved it," Connolly says of the training. "What a rush. You're totally focused; you can't think about anything but the track in front of you." "I'm still terrified," Ferrara counters. "I don't want to drive 150. I'm just not built that way. I don't even like to drive. I get anxiety when I have to go over Laurel Canyon. I put on sports-talk radio just to distract myself."

"Yeah, I usually drive like a grandma," Grenier says. "I don't mind driving conservatively." He pauses, then smiles and adds, "Apparently I have a natural gift for it, because I blew the other guys off the road."

That's one of the great things about this particular boys' club: Everyday at work is a new adventure of recreational pursuits and party-animal indulgences, from the beach at Cannes to the Playboy Mansion to a day spent driving high-performance cars around a professional track.

"Look at all the things we get to do—here I am spending a day at the golf course and the racetrack," Connolly says.

Adds Ferrara, "We got to sit courtside at the Lakers, go to Sundance and Cannes. I'd never even left the country before. You know, I never thought I'd be doing comedy. I thought of myself as the kind of actor who would be crying in scenes, not as a comedy actor. Comedy is hard."

If "Entourage" is an unexpected hit, its breakout character is even less likely: Ari Gold, the Hollywood agent with the fastest, sharpest tongue in town. Jeremy Piven has won three Emmy Awards and a Golden Globe in five seasons of playing Ari, Vince Chase's überagent. Ari works like a maniac to keep Vince's career rising—and, at times, from self-destructing—while negotiating the Byzantine intrigues of the industry's corridors of powers, leaving no one (except Vince) unflayed by his rudely pragmatic and always outspoken assessments of the world around him.

"Is it me or is her voice getting worse?" Ari mutters aloud as he listens to his daughter practice for her bat mitzvah. When his wife scolds him, he says, "It doesn't mean I don't love her, but she's just awful, baby."

Based on real-life agent Ari Emanuel(whose clients include Wahlberg, Scorcese and Jessica Alba, all of whom have been on the show—and whose brother is Rahm Emanuel, White House Chief of Staff), Ari Gold makes abrasiveness an art: Even when he's trying to be nice, there's a sting to him. In the very first episode, he offers to reconcile a disagreement with Eric by uttering the now immortal line, "Let's hug it out, bitch."

"Everyone," Piven says of Ari, "needs a shark in their life. And everyone wants someone who is completely passionate to represent them. I think that's what he is."

Yet the character of Ari really was underrepresented in the pilot. "We didn't envision him as a series regular," HBO's Lombardo says. "But once we saw Jeremy and saw how well he worked and interacted with the guys, he became the fifth member of the crew."

Piven, 43, had his own hesitations about taking the part. He'd had good roles on a couple of hit sitcoms—"Ellen" and "The Larry Sanders Show," as well as "Cupid"—and had worked his way up to supporting roles in films such as Old School and Runaway Jury, when the "Entourage" pilot came his way.

"I had one scene in the original script," Piven recalls. "And I'm going to sign a contract to do a piece where I play the sixth lead behind a character named Turtle? But I saw potential in the character."

"Jeremy inhabits Ari in a way I never would have imagined," Lombardo says. "We haven't seen that character before."

The challenge, Piven notes, is to find the vulnerability in a man swathed in a seemingly invincible shield of withering sarcasm and scorn for the world—to make audiences care about more than whether his next one-liner is as wicked as his last one. "Call me Helen Keller because I'm a fucking miracle worker!" he crows at one point.

Says Piven, "I try to make him as accurate as possible, with dramatic license. So he's wildly abrasive but dedicated to his family. He's an absolute pig who is also absolutely monogamous. It's our job to make sure the audience doesn't just write him off, that Ari doesn't alienate people. There are times when I say something and I'll think, Everyone is going to turn on me with that one. Ari Gold wouldn't have the patience to represent Jeremy Piven."

Unlike Ari, Piven does enjoy the occasional cigar, as he demonstrates on this issue's cover.

"I've been smoking them for about 15 years," he says. "I stumbled into it when I first visited Cuba. Once you taste a great, smooth cigar, it's hard to go back. "I try not to abuse the privilege of cigar smoking," he says. "I'll usually have one at the end of a long day, like a celebratory moment after putting something extra into the work. I've never had the opportunity to smoke in character—I don't know if Ari would. He's such a Type-A wrecking ball. He probably wakes up at dawn and goes running, as the boys are coming home from the clubs. But if it was a case of wooing Ridley Scott, he'd be knee-deep in the Montecristos."

With its blend of inside jokes and real-life stars playing themselves, the line often blurs between life and art on "Entourage."

"Everything you see on the show has happened to someone," Dillon says. "None of it is make-believe. Most of it happened to one of us on the show."

Log in if you're already registered.

Or register for Cigar Aficionado today—it's free.

Registration allows you to:
  • Keep track of your favorite cigars in your personal humidor.
  • Comment on all our stories.

Forgot your password?

Ratings & Reviews

Search our database of more than 17,000 cigar tasting notes by score, brand, country, size, price range, year, wrapper and more, plus add your favorites to your Personal Humidor.