When Entourage hit HBO in 2004, there was a bit of a sigh of relief, and not just by those who have a particular taste for pay-cable nudity. The idea of a show actually depicting and, by extension, analyzing the behind-closed-doors dealings that popular, up-and-coming actors face when their buzz peaks is immediately fascinating and for a moment, it seemed that Entourage might have been that show. This coupled with Vince and E’s business partnership made all the bro-dog bullshit borderline palatable for the first three seasons or so of the series, before the frat-boy mentality, nudity, and increasingly unconvincing plot turns took over.
Still, the storylines that actually focused on the film industry in Entourage – the Aquaman roll-out, the Escobar-movie fiasco, the dealings with Warner Bros., etc. – resonate because they offered a view of the working industry rather than all the glitzy benefits of a glamorous lifestyle. Even if Entourage wasn’t the long-form insider glimpse it once looked to be, there’ve been plenty of works that have offered rousing insight into the process. There’s an irresistible allure to films about filmmaking because they seem to be immediately reflexive, a peek into how the work you’re watching got made or how those who made it got where they are. At their best, these sorts of films lend expressive force to the art and craft of making moving pictures while simultaneously deconstructing the luck and endless toil that went into creating these images.
So, in honor of what Entourage might have been, I decided to go through 10 of the very best films focused on the business of making movies, touching on a variety of angles explored in a vast array of artists who have seasoned perspectives on the impossible, demanding work of making what audiences are happy enough to refer to as “movie magic.”