There is no career path stranger than Justin Theroux's, yet it has culminated in something you might have predicted for him in 2001 when he emerged as one of the stars of David Lynch's Mulholland Drive. "Sure, that guy could go on to be the lead of an HBO series one day," you might think. But would you have predicted stops along the way that included playing a thick-necked Irish villain in a Charlie's Angels sequel or working as a writer-for-hire for mediocre Hollywood blockbusters? Theroux is doing great work on The Leftovers and is constantly in the tabloids because of his romance with Jennifer Aniston, but let's deep-dive back in his career and see how he got here.
Theroux had a bunch of memorable but very minor roles before showing up in Mulholland Drive. He had a small part in Mary Harron's great indie I Shot Andy Warhol and a little more to do as a suit in her follow-up American Psycho, he was two separate loser guys on Sex and the City (more famous as the premature-ejaculating Vaughn Wysel), and he's Clarence the Cowboy in Romy and Michelle's High School Reunion. His showdown with Janeane Garofalo's Heather Mooney in that film is pretty much its best scene.
But Mulholland Drive was what put Theroux on the map. Originally filmed as a pilot for ABC, Theroux probably was the most stiffed by Lynch re-editing it as a film after the network turned it down, because he has the least to do in the dreamlike post-script Lynch added on, and there's so many dangling plotlines that could have been explored in a TV series version. But he's still great as a wise-ass director whose life unravels underneath him—his own creepy confrontation with a cowboy is another highlight.
Theroux's co-star Naomi Watts immediately vaulted to super-stardom, but he bounced around in a bunch of frustrating supporting roles that only made a little bit of sense for him. He's incredibly committed to his work in Charlie's Angels: Full Throttle, as muscular bad-guy Seamus O'Grady, but why was his first role in two years the secondary villain in a mostly unnecessary sequel? It didn't help that Full Throttle was a relative box-office bomb.
After that, Theroux goes sadly quiet. Between 2003 and 2008, his best work was as Brenda's rebound lover Joe on eight episodes of Six Feet Under, where he was very likable and compassionate, but the character didn't last that long. He made some decent alt-comedy movie choices, popping up in The Baxter and Strangers with Candy, but none of the roles were particularly interesting. Other casting decisions seemed more promising—he's part of the squad in Michael Mann's Miami Vice and reunited with David Lynch for Inland Empire—but those are sadly more background roles than anything else.
I was still firmly in the Theroux camp in 2008, but I couldn't deny he hadn't lived up to the wonderful potential he showed in his first few roles. Then I was especially surprised to see his name attached as a screenwriter of Ben Stiller's Tropic Thunder. Theroux had directed an indie, Dedication, that was released the same year and went nowhere, but Tropic Thunder was a big hit that topped the box office four weeks in a row. All of a sudden, Theroux was an in-demand writer: he was tapped to script the Marvel sequel Iron Man 2, on which he is the sole credited writer, and he also took a pass on Rock of Ages. The weirdest credit of all: he's an executive producer on 2010 DreamWorks Animation comedy Megamind. Gotta wonder why that happened.
Tropic Thunder really holds up, but Theroux's big-studio efforts were both critical flops, and Iron Man 2 remains the most-reviled Marvel Studios film, although it made plenty of money. Hard to know whether Theroux is at all to blame there—Marvel meddling to get its burgeoning Cinematic Universe in order probably played a big part—but still, he's the only writer listed, so he has to shoulder some of the blame. Rock of Ages' flaws go far beyond Theroux, but still, he hasn't written a movie since.
Theroux started dating Jennifer Aniston in 2011 after meeting her on the set of Wanderlust, where he played—guess what—a handsome villain type. At least in Your Highness he played an ugly villain, but that movie was too demented to really make a dent in the public mindset. Honestly, his biggest exposure outside of Aniston over the last few years was probably his brief stint as a love interest for Leslie on Parks & Recreation who just turned out to be too perfect.
In a way, it's almost surprising that Theroux landed the lead role in HBO's next prestige drama, but the potential has always been there. Go back to Mulholland Drive and you'll see a guy who's equally good at being slapstick funny as he is silently furious. Thirteen years later, his work as Kevin Garvey, a repressed, angry, confused chief of police wrestling with the breakdown of his family following a global rapture, is an even darker echo of that. We're only one episode in, but The Leftovers could well be the next phase of Theroux's career—the only real question is what curveball he'll throw next.