Pop culture obsessives writing for the pop culture obsessed.

Every day, Watch This offers staff recommendations inspired by a new movie coming out that week. This week: The Skeleton Twins, featuring serious turns from former SNL co-stars Kristen Wiig and Bill Hader, has us thinking about other dramatic departures from comedic actors.

Permanent Midnight (1998)

In 1998, Ben Stiller starred in three films released within a month of each other—the Farrelly brothers’ There’s Something About Mary, Neil LaBute’s Your Friends & Neighbors, and David Veloz’s Permanent Midnight—that may as well have been an audition reel demonstrating his range. At the time, Stiller was still primarily known as a sketch comedian (to the dozens who’d caught The Ben Stiller Show, anyway) and a director of films like Reality Bites and The Cable Guy, with a single role in David O. Russell’s Flirting With Disaster to prove he also had a certain neurotic edge. By starting the summer of ’98 playing the hapless dork, then ending it as a pair of amoral jerks, Stiller was all but asking audiences—and himself—to choose which version of him they preferred. A half-dozen Night At The Museums and Meet The Parents later, it’s pretty obvious which path he picked.


Still, a career of mostly playing the put-upon everyman only makes revisiting Permanent Midnight all the more fascinating, as it’s the rare Stiller performance that takes all the sublimated rage and barely suffered indignities that underscore so many of his characters, then dares to remove any shred of audience sympathy. Stiller stars as real-life screenwriter Jerry Stahl, whose tell-all of the same name spilled all the grisly comic details about his days working on TV shows while also burning through a $6,000-a-week heroin habit.

As Stiller plays him, Stahl is a black leather-clad ball of resentment who’s openly contemptuous of the ALF-like sitcom he’s slumming on (despite it being staffed by likable goofballs Fred Willard and Charles “Roger Rabbit” Fleischer) and only productive when he’s high, when the drugs combine with his preening overconfidence to create a manic state. But even while everyone constantly validates Jerry’s incredibly high opinion of himself by kissing his ass and suggesting he’s meant for bigger things, he can’t help but squander these mediocre opportunities. Stiller, who so often plays the victim of circumstance, is here asked to be a straight-up dick.


That’s especially true of Jerry’s relationships with all the beautiful women who simply can’t stop throwing themselves at him, so taken are they with his hangdog misanthropy. Of course, it’s in these moments that Stiller feels most miscast: Would the likes of Maria Bello and Elizabeth Hurley really be so attracted to Ben Stiller as to ignore his many, many personality failings—and in Hurley’s case, his tendency to ignore her in favor of mainlining in the bathroom?

It’s a question that director David Veloz, in his sole turn behind the camera, apparently never stopped to address. The Natural Born Killers screenwriter seems far less interested in making sense than in sensory overload, casting pretty faces in thankless roles the same way he fills his soundtrack with pulsing techno music—as a means of amping up what is often just a series of shots of Stiller jabbing needles into himself, then spritzing the ceiling with his blood. Sometimes this works in his favor, as in a scene where Jerry is hounded by hallucinations of his puppet, or a standout visual sequence of Jerry and his dealer getting high on crack, then flinging themselves against the interior windows of a skyscraper. But it’s a tricky balancing act between black comedy and junkie melodrama that, for all of Stiller’s palpable sweat, the film struggles to pull off.


Still, while Veloz’s jarring sense of tone and Bello and Hurley’s woefully underserved characters help make Permanent Midnight a misfire, it’s Stiller’s performance that at least makes it an interesting one. Even working opposite his usual foils—Janeane Garofalo, barely concealing a smirk as Jerry’s would-be agent; Owen Wilson, his rambling spaciness explained here by on-screen Percodan abuse—Stiller is a hollowed-out shell of his usual smartass self. A scene where Jerry blows his audition for another cheap sitcom, slinking into the room dressed in a ridiculous green gangster suit then slurring through his pitch, is particularly wrenching; Stiller lets you see how pathetic Jerry’s manufactured “cool” really is, even as he remains totally oblivious.

In some ways, it’s a performance reminiscent of Dustin Hoffman’s in Lenny, if Lenny Bruce had been a total hack. All of Jerry’s supposed suffering is for art even he knows is garbage, which makes his inability to rise above the junk he shoots up his arm and the junk he spews on the page all the more tragic. And amid a career of playing lovable losers, it’s a reminder of the darkness Ben Stiller is capable of accessing, when he’s actually willing to lose.


Availability: Permanent Midnight is available on DVD, which can be obtained through Netflix or your local video store, and to rent or purchase through the major digital services.

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