The True Tragedy of Entourage

By  · Published on March 25th, 2015


“Like I told you fifteen years ago, the next level is coming.”

When Entourage first hit HBO in 2004, the Hollywood-set comedy series promised to chronicle the intricacies and hardships of making it in the entertainment industry, with lots of laughs and plenty of hot babes to spare. The series was ushered to the small screen by a large group of producers, but most notable among their ranks was Mark Wahlberg, who had no problem telling the press that the wild tales of rising star Vince Chase (Adrian Grenier) and his childhood pals were loosely based on his own experiences breaking into Hollywood. At the time of Entourage’s creation, Wahlberg had been in the acting industry for nearly a decade (pants-dropping singing career notwithstanding), and was undeniably on the cusp of breaking into superstardom (of Wahlberg’s 15 highest grossing features, only four of them were made pre-Entourage, and only one of them – The Italian Job — could rightly be referred to as a Wahlberg star vehicle).

For Wahlberg, the best was yet to come, and a series that was ostensibly about his rise to fame seemed both funny and prescient. The tragedy of Entourage, however, is that such a promise never came true for the people who actually played wannabes on the small screen. The stars of Entourage may have become extremely successful within the confines of their characters, but they’ve been mostly unable to transfer fake triumph into real results. Entourage is about megastars, but it stars people who will never be as successful as their fictional characters.

That’s rarely been clearer than it is in Entourage the film’s latest trailer, which clarifies the plot of the feature – one that was demanded by both dedicated fans and its own creative team behind it – and the narrative’s continued obsession with making it in Hollywood, all while being lead by actors who don’t typically topline highly anticipated summer features.

One of the overarching stories of the series involved Vince’s casting as Aquaman (a film that is actually happening now, again, Entourage was both funny and prescient) in a major motion picture. Vince did star in the film – which, in the world of Entourage, is the highest-grossing film ever, one of many excellent tidbits provided by the truly excellent Entourage Wiki – even though he eventually jumped ship on returning for more ocean-set outings as part of his desire to do Medellin, an indie picture he was long drawn to star in. By the time Entourage the film picks up, Vince is back on top (something he struggled with doing during the show’s final seasons) and looking to do something new: direct.

Vince’s professional arc is a believable one, and one that befits a superstar, which makes the lesser star power of its leads – from Grenier to Jeremy Piven — all the more resonant within the context of the show. This is a show about success. It stars people who are not as successful as the people they play. This is somehow both funny – oh, Hollywood, you minx! – and kind of depressing.

Grenier wasn’t a newbie when he took on his leading role in Entourage, the role that he will likely be most remembered for, as long as his own career sticks to its current rhythm. The actor had already starred in a handful of films before becoming Vince in 2004, including romantic comedies (Drive Me Crazy), war films (Hart’s War), and dramas (Hurricane Streets). He exhibited both range and a genuine interest in different kinds of movies. Still, he’s not a major movie star and he’s never toplined a blockbuster hit. In short, he’s not Vince, and that he plays him is occasionally bizarre to think about, if not outright meta. (Grenier has explored other options beyond the Vince path, including drumming in his own band, directing two documentaries and a short, and showing a strong dedication to various charitable endeavors.)

Piven too is not a bankable movie star on his own – though he’s certainly got name recognition – but he’s expanded out his own career to include movie parts, his own television series, and plenty of on-stage work (the actor comes from a very well-regarded theater family). Elsewhere, Kevin Connolly has turned his attentions to directing, while both Jerry Ferrera and Kevin Dillon have mostly dabbled in supporting roles. But for all the stars of Entourage, the upcoming film will be their biggest feature (with their biggest roles) in years, if ever.

It’s telling that on each of the star’s Wikipedia pages, one of the first things that is indicated in their top biographies is that they are “best known” for their individual roles on Entourage, a story about making it in Hollywood, as told by people who haven’t done it quite yet.