Overnight, co-directed by Tony Montana and Mark Brian Smith, is like some unholy meld of Project Greenlight, Entourage and the biggest asshole you've ever met. In 1997, Boston nobody Troy Duffy snagged a widely publicized $15 million deal from Miramax to direct his script The Boondock Saints. Duffy moves his crew -- a collection of bar buddies who now function as a production team (and who double as members of Duffy's sludge-rock band, The Brood) -- to Los Angeles. The gang also includes Montana and Smith, who document Duffy's rise and fall after his film deal, and it's their footage that comprises Overnight.
Their film is amateurishly produced, and it quickly becomes clear that Montana and Smith have a personal agenda: to portray their former colleague Duffy in the worst possible light. As such, while Overnight purports to be about the contemporary filmmaking scene, it lacks larger context as well as specific details (we never even learn how Duffy snagged his deal). But even if it's sloppily constructed and personally vindictive, it's still fascinating as a warts-and-more-warts snapshot of the Hollywood film machine.
Ironically, it's the increasing volume of "insider" material (mags, memoirs, movies like this) that helped create the contemporary monster that is Troy Duffy. He's not just a standard-issue showbiz diva fueled by what he perceives as his unique creative gifts; he's also a gigantic pain-in-the-ass bore who reckons that he -- a profane bartender from Boston -- knows the secrets of the system. His mantra runs something like, "I know they're fucking me, but there's no way they can fuck with me because those fuckers need me, and I'll fuck them first because I'm fucking smarter."
The film never answers the question why Duffy's much-abused posse bothers to stick around, nor does it track down anybody outside the gang for their opinion (why did Miramax dump the Saints deal?). Chalk it up as home-movie-as-revenge with a high-profile narrative and a star you're gonna love to hate. The largely clueless and unlikable Duffy unspools enough rope to hang himself a hundred times. It's not necessary to have seen The Boondock Saints (which Duffy ultimately made with another production company). But having watched it, and knowing that Saints is a witless turd of a movie, makes Duffy's furious raves about how he is breaking all the rules, how his film is too good to be made, truly gut-busting.
In the end, Duffy is left fuming, still mired in his megalomania and convinced that global conspiracies are impeding his desires. Maybe when he sees Overnight, he'll cop to the truth: Just because you're a braying asshole doesn't guarantee success, even in the high-octane cesspool that is Hollywood. And for the rest us of us, the film is a herky-jerky roller coaster of a schadenfreude ride: For once, bad things happen to bad people.