Cigar Aficionado

After five seasons, HBO's "Entourage" already had a high cool factor—but an endorsement from President Barack Obama?

Now that's serious.

Here's the most popular president in recent memory—and he's given his seal of approval to a sometimes-edgy, inside-Hollywood comedy series about a rising movie star and the childhood friends who keep him grounded.

According to an April article on the Web site Politico.com, Obama regularly rearranged his campaign schedule in 2008 to make sure he didn't miss any episodes. As White House press secretary Robert Gibbs told Politico, "We would talk about 'Entourage' all the time."

Adrian Grenier, who plays actor Vincent Chase, the central character in "Entourage," says, "When Obama said he enjoys the show, I thought that's absolutely perfect—because he embodies the spirit the show represents. A lot of people dismissed it as a show about the superficial nature of a movie star's life. But it's a show about how to navigate in that superficial world, how to be loyal and true to your friends."

Kevin Connolly, who plays Eric Murphy, Vince's best friend and manager, says, "I thought, 'Holy shit'—the Obama thing is huge. I mean, we still wait to see if the show will get picked up each season—and here's the president, giving us a shout-out."

Not bad for a show that many observers initially considered too esoteric to have a future. When "Entourage" went on the air in 2004, even its network wasn't sure audiences were interested in the behind-the-scenes story of Vincent Chase, a young actor from Queens, New York, and his lifelong friends (including a half-brother), who comes along for the ride when Vince's career takes off in Hollywood.

"When we looked at it, we wondered whether it was too inside," says Michael Lombardo, president of HBO's programming group. "But that was part of the fun. Over the past six years, things like box-office grosses and ratings have become the fodder of popular culture. Everybody touches show business in some way—even if only as a consumer, a , a fan. So pulling the curtain back on that has become of interest to a wide spectrum of people."

Actor Jerry Ferrara, who plays Turtle, Vince's driver, gofer and all-around fixer, says, "One thing that did surprise me was that the interest in the inside-showbiz stuff was so universal. People in Middle America love to hear inside jokes about people like (filmmakers) Kevin Smith and James Cameron." Says Jeremy Piven, who plays Ari Gold, Vince's turbocharged agent, "This is a celebrity-driven culture. The writers work as hard as they can to make it as real as possible."

Lombardo concludes, "It's evolved into one of the signature programs in of defining HBO. It's continued to grow and develop. This season, we'll explore them going from their 20s to their 30s and the challenge of remaining friends as men."

The show has never been a ratings bonanza—nowhere near the tens of millions of viewers "The Sopranos" drew—but its audience has grown steadily, particularly in a demographic HBO is eager to reach: young men. It's averaged about six million viewers a show since Season 3a (which ran in 2006), hitting a high of about 7.4 million during Season 3b (which had the final season of "The Sopranos" as its lead-in).

Anecdotal evidence suggests that ratings don't reflect audience size, since groups of men—whether frat brothers or stockbrokers—gather to watch Vince Chase and his boys navigate the showbiz sharks and aren't counted individually. "It speaks to an audience—young males—that some of our other shows don't," Lombardo says. "And yet it is quintessentially HBO."

HBO doesn't release figures for the sales from DVDs of their series. But the Season 5 DVD, which wasn't released until the end of June, was No. 7 on the comedy TV show best-seller list (based on preorders) at Amazon.com in mid-May and No. 162 among all movies and TV shows.

About to launch its sixth season on July 12, "Entourage" has become a benchmark in another way: a place where movie stars and other celebrities pop up in cameo roles playing themselves—often as part of a joke at their own expense. Everyone from golfer Phil Mickelson to rapper Snoop Dogg, from actor Gary Busey to director Martin Scorsese, have made appearances. New England Patriots quarterback Tom Brady and "West Wing" writer-producer Aaron Sorkin have scenes in the can for the coming season.

"Season 1, we couldn't find anyone willing to be on," says Kevin Dillon, who plays Johnny "Drama" Chase, Vincent's half-brother, an actor who struggles in the shadow of his younger sibling's success. "Now, every year when we go to the Golden Globes or the Screen Actors Guild awards, all these other actors seem to be into it—they're all offering to do the show."

But the show's success and popularity come from something deeper than the Hollywood plots and movie-star walk-ons. Says Doug Ellin, the show's creator and executive producer, "At the end of the day, it's a show that's about friendship more than Hollywood."

It's a bright morning in City of Industry, east of Los Angeles, but the tee box of the driving range at Pacific Palms resort is still being lavishly lit for a TV shoot.

As the crew arranges lights around one specific tee, Jerry Ferrara practices with his driver a few stalls away, taking the opportunity to sharpen his swing. "I didn't play golf before this show," says Ferrara, 29. In Season 4, the Vincent Chase crew is riding high, living in a mansion outfitted with a golf simulator. Dillon, a long-time golfer with a 7 handicap, taught Ferrara to play, first on the simulator, then on the golf course. "He's, like, my coach," Ferrara says.

"Your caddy," Connolly jokes.

"Never my caddy," Ferrara says solemnly.

As director Mark Mylod, one of several different directors for the 2009 season, settles into a chair in front of two small video monitors taking feeds from two cameras, two golf carts are readied for the scene. Assistant directors place extras—mostly golfers and good-looking women—around the set, giving them bits of business to do as part of the background action.

The scene itself is a key moment in the new season's third episode: a meeting between Connolly's Eric Murphy and guest star George Segal, as Murray Berenson, a Hollywood business legend who runs a major management firm. When Vincent Chase's career flourishes in Season 6, Murphy—known to all simply as E—will find that he needs to devote his energies to his primary client and will fold his fledgling Murphy Group management business.

As the scene begins, E is hitting golf balls with Turtle on the driving range, warming up for a celebrity pro-am tournament. Turtle complains that he's not playing in a foursome with a celebrity, and E chides Turtle, a die-hard New York Giants fan, on his rudeness when they met Tom Brady. When Murray Berenson rolls up in his cart and introduces himself, he asks E to ride with him. "I heard you closed down your little shop," Murray says as they roll away to end the scene. "And I wanted to talk to you about coming to work at my big shop." Mylod watches a rehearsal, gives some final words of direction to the actors, then dons headphones and sits down to watch the multi-camera take on the video monitors.

"This is actually the second part of a scene we shot a month ago," Mylod its. "Normally, we're more organized."

Mylod, who is also a co-executive producer for the show, says, "I've had a real sense of the show maturing for this season. That keeps it relevant and gives it direction. It keeps evolving."

Over the first five seasons, Ellin and his writers have populated their version of Hollywood with characters who do battle at all levels of the film industry. As Vincent Chase and his friends struggle, hustle, score, flop and, occasionally, retreat, they inhabit a world that is at once highly specific and completely universal. The showbiz plotlines are funny—but so are the stories that focus on their individual quirks.

Yes, there's comic tension over whether Vince will get a part he wants. But episodes can be built around something as simple as E's denial that he tends to become emotionally involved with every woman he sleeps with (which generates a contest between E and Turtle to see who can talk his way into a one-night stand first). Or Ari's struggle to get his son into an exclusive private school. Or a movie deal that has to be completed in a single day, that day being Yom Kippur, when most of the deal's participants, theoretically, would be worshipping—and forbidden from doing business.

That's a long way from the original "Entourage" vision: a barely fictionalized version of actor Mark Wahlberg's Hollywood experience. The former teen rapper came to Hollywood as a music heartthrob, surrounded by a crew of pals from his Boston boyhood, hoping to break into films. Wahlberg made shrewd choices of movie projects and, in short order, became an actor whose résumé includes films by Martin Scorsese (The Departed), Paul Thomas Anderson (Boogie Nights), Tim Burton (Planet of the Apes) and David O. Russell (Three Kings).

"When we started, this was going to be about an A-list star and his crew," Ellin says. "Well, Vince is almost A-list—but not quite. I'm sure that nobody expected us to spend five years keeping him down."

In fact, Ellin never plotted out a long-term outline for the show. Though he spent several years developing "Entourage" before HBO finally bought the pilot, he hadn't really thought beyond that first episode.

"When we made the pilot, I had no idea what Episode 2 was going to be," he says. "I make it up as I go along. The show has grown in ways I never would have anticipated. If you had told me that Turtle would wind up dating a hot actress [Jamie-Lynn Sigler of "Sopranos" fame], I'd have said you were out of your mind."

Vince Chase gets the rising-star treatment in the show's first episode, with the impending release of his first major film, Head On. But instead of tracing Wahlberg's upward trajectory, Vince charts an unsteady, obstacle-strewn course, never seeming able to do anything the easy way.

Vince remains the group's calm, cool nucleus, though he does give in to momentary panic near the end of the last season, when his career seems to hit bottom. But in the closing moments of the final episode, Martin Scorsese calls to cast Vince as the title character in a Great Gatsby remake.

"Vince's Zen approach to life really expresses how best to navigate this world, because it is a fleeting experience," says Grenier, 32. "It's easy to get lost, to feel inadequate.

"Vince has had some difficult times. This season, he's actually able to appreciate the fun he's had in the past because he's been through moments of difficulty. This year, he's got a new joy and relish, which comes with the perspective of having gone through difficult times. It makes him enjoy the good times more."

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 ionate 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 ing 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."

"We get stuff from all over the place," Ellin says. "The stuff about Vince flying on someone's private jet—when Kevin was starting, he had friends who were bigger stars who would charter a jet to Vegas and invite him along. It's stuff I read in the papers, personal things."

The message "Entourage" sends about fame is that it moves quickly, burns hot and is easily upended, given the speed of the nonstop news cycle. Fame is a club, to which only the very lucky and the very ruthless are offered hip—and ongoing hip is never guaranteed.

"It's the modern mediated experience—we've all been quite well-schooled in how to perform," says Grenier, who has directed a documentary, Teenage Paparazzi, about celebrity-obsessed culture. "Doug Ellin has tapped into the zeitgeist. He's done a genius job of extracting the relevant cultural moment and infusing it into this show."

"I've had the experience—friends who went from being nowhere to being major stars and then they disappear," Ellin says. "Show business is a very up-and-down existence. Most other professions don't really have that."

There's also the absolute tang of testosterone when these boys from Queens are dealing with their personal lives together. They've all had woman problems—but their solution is usually a trip to Vegas. It's not very often these guys sit around and discuss their feelings or needs beyond the basics ("I need to get laid!").

"I don't think we ever saw it as a male version of 'Sex and the City', though others said that," Lombardo says. "Each of these shows explored friendship. And each has at heart a city as a central character. But I think that's where the comparison ends."

But beyond the red carpets, girls, glamour and prestige, "Entourage" is about four buddies who have each other's backs, no matter what.

"Yes, it shows how cutthroat the business can be, it shows a lot of backstabbing—but it also gives a strong message about friendship," Dillon says. "That's what makes the show work: the bond, the friendship. That's the heart and soul of the show."

"Who doesn't understand family and friendship?" Grenier says. "Having the business as the backdrop is just for shits and giggles. We could all be playing locksmiths and be just as compelling."

HBO's Lombardo says, "Obviously, I'm a big fan of Ari Gold and his agency; they get that so spot on that I just giggle. But there's always a moment in each show that moves me and reminds me that friendship transcends everything."

Meanwhile, getting back to the show's First Fan—what are the odds of an unexpected appearance on "Entourage" by President Barack Obama? "You couldn't beat that cameo," Ferrara says, to which Connolly adds, "Not by a long shot. That would be a real coup."

Says HBO's Lombardo, "I'm sure Doug is working on that right now." Not really, says Ellin: "I think there could be some downside for Obama with that."

Marshall Fine is a journalist and film critic whose movie reviews can be found at www.marshallfine.com.