“Maybe you can have it all” was a tagline used to promote Entourage’s third season, but it may as well have been the series mission statement. Fifteen years ago today, HBO introduced us to Vincent Chase, and one of the most alluring, enduring and yes, mostly male-oriented wish-fulfillment sagas was born.

Entourage isn’t a comedy though it was often funny and at times hilarious, it’s a living daydream grounded in the reality of everyday celebrity life, where even the banal is casually glamorous. Through Vince and his three childhood friends shamelessly living off of everything his emergent movie-star status affords them, the series was one half-hour fantasia of testosterone-fueled material delights after another.

But of course, there was more to Vince’s friends than clout and there was more to Entourage than foreign cars, gorgeous women and A-list cameos. At its best, the series celebrated genuine, ride-or-die camaraderie and loyalty—season 1’s tagline was “His fame is their fortune” but the series often posited Vince’s life as only being enjoyable by his ability to share the wealth, a borderline co-dependent. It also plumbed the depths of the Hollywood industry machine, offering a glimpse behind the curtain so authentic early viewers wondered if it wasn’t scripted. Even amidst detractors who argued the show reveled in surface materialism and lazy arcs with no stakes, Entourage’s hold on the zeitgeist only grew as it continued. Jeremy Piven as Vince’s bulldog agent Ari Gold became a breakout and Emmy/Golden Globe mainstay, in an ensemble that already included singular oddities like Kevin Dillon's perennially struggling actor Johnny Drama or Jerry Ferrara's baby-faced master finesser Turtle. Under the stewardship of music supervisor Scott Vener, who came aboard in season 2, the show's soundtrack became a phenomenon unto itself, with A-list rappers even opting to premiere songs in an episode. In plotting Vince's career as the gang traversed upward mobility in the movie business, creator Doug Ellin inadvertently predicted several trend paths Hollywood would go down. Call it incidental, sure, but it also belies a deeper understanding of Tinseltown than the show is given credit for.

Eight seasons and a movie later, the show's merits are in constant debate but its legacy is unquestionable. In honor of the series premiere, which bowed on HBO Sunday July 18, 2004, Complex wrangled Ellin, ostensible series lead Kevin Connolly, Ferrara, Dillon, and veteran executive producer Larry Charles to reminisce on making the pilot that led to the job of a lifetime. Read on for an oral history reflecting on the early days of the series, how it grew into the ratings hit we know today, and their thoughts on why it resonated.

The Entourage:
Doug Ellin - creator, writer, executive producer
Kevin Dillon - Johnny Drama, Vince's older brother
Kevin Connolly - Eric "E" Murphy, Vince's best friend and manager
Jerry Ferrara - Vince's best friend and driver
Larry Charles - executive producer 2004-2009, writer 2004-2005

Also Watch

Close