The last time we saw movie star Vincent Chase (Adrian Grenier), he was jetting off to Paris to marry a Vanity Fair writer after a whirlwind courtship. That was in 2011, when the HBO series bid farewell after eight moderately successful seasons, but when this film opens in 2015, somehow only six days have passed -- and his marriage hasn't lasted a week. Even though he's alone on his honeymoon, in Vinnie's charmed life that means, of course, hanging out on a gigantic yacht off the coast of Ibiza with scores of other carefree passengers, most of whom are beautiful women in various stages of undress.
Luckily for our hero, help is on the way: A speedboat ferries in his best buds -- manager, producer, and longtime friend Eric (Kevin Connolly); older half-brother Johnny Drama (Kevin Dillon); and gofer-cum-tequila mogul Turtle (Jerry Ferrara) -- for a sun-drenched, seafaring reunion. Throw in a phone call from his former agent Ari Gold (Jeremy Piven), and the whole gang are back together. Ari, who's now running a studio, wants his first movie to star Vinnie, but Vinnie announces that he also wants to direct the picture, a declaration that stuns his pals and is met with crickets on the other end of the line.
Flash forward a few months: Vinnie's project, the Robert Louis Stevenson-inspired Hyde, is nearly complete, but he needs more cash to finish editing. He's already over budget, however, and Ari is forced to fly to Texas to grovel before the film's financier, billionaire Larsen McCredle (Billy Bob Thornton), for another 10 million dollars. Larsen is skeptical, so he sends his son Travis (Haley Joel Osment) back to California with Ari to assess whether it's worth writing another check. A poster child for despicable, spoiled scions with more dollars than sense, Travis attempts to worm his way into the Hollywood elite, but soon learns there's only so much his money can buy.
Travis' story line gets old fast, which is a shame because it dominates the latter half of the film; when his real reservation about Hyde is finally revealed, it's petty, high-school stuff. Just about everyone has a good reason to throttle this kid, but his grasp on the purse strings gives him all the power, and he practically stomps and pouts if someone forgets it. Maybe that's just Hollywood, but as villains go, it's pretty weak tea.
Series creator Doug Ellin, who writes and directs here, has stated that he wants the film to appeal to people who never saw the HBO show on which it's based. As a result, the characters are fleshed out quickly: Vinnie is eternally optimistic; Johnny is still looking for his big break; Eric and Sloan (Emmanuelle Chriqui) aren't a couple at the moment, but she's having their child; and a newly svelte Turtle's booze business might finally give him enough clout to date someone like MMA fighter Ronda Rousey (who plays herself). As for stressed-out Ari, his profane outbursts, as always, come made-to-order, whether he's losing his cool at couples therapy with his wife (Perrey Reeves) or callously dismissing a sincere request from his former assistant Lloyd (Rex Lee).
Fans of the show will find a lot to like here, and the dozens of celebrity cameos -- which include Jessica Alba, Warren Buffett, Kelsey Grammer, Liam Neeson, Ed O'Neill, Mark Wahlberg, Pharrell Williams, and Russell Wilson -- also lend a feeling of familiarity. Oh, and so do Johnny's 1965 Lincoln Continental, the theme song "Superhero" by Jane's Addiction, and the obligatory unhinged appearances by Bob Saget, Gary Busey, Andrew Dice Clay, and fictional director Billy Walsh (played by Rhys Coiro). Ultimately, these retreads subtract more than they add, causing the film to drag on (and on) as if it's a 104-minute episode. Entourage doesn't break any new ground, but maybe that's because, like the shallow Hollywood culture it mocks, it never aspires to dig that deep in the first place.