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

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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, 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 user, 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 terms 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 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 admits. "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.

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