June 8, 2011 12:30PM ET

How Zach Galifianakis Became Comedy Royalty

From ‘Boston Common’ and ‘Apt. 2F’ to ‘Bored to Death’ and ‘The Hangover’

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A few short years ago, Zach Galifianakis’ fanbase was mostly made up of critics and the comedy cognoscenti. Now even your grandmother has grown familiar with his bushy bearded face, a fixture on billboards everywhere. As overnight as his fame may seem, though, Galifianakis has been quietly paving a path toward stardom since his sitcom days in the mid-Nineties. Here are the most significant stops he’s had along the way, some more hysterical than others – but nearly all of them showing that the prickly comic with the deadliest deadpan deserves every bit of his success.

By Joe Berkowitz with Matthew Perpetua

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After making the leap to Los Angeles from New York, Galifianakis found his first recurring TV role on the network sitcom Boston Common. It was the eighth-highest-rated show in its first season, but after switching nights in its second year, the show dropped to 51st place and was quickly cancelled. The fledgling comic actor soon moved to a new MTV show called Apt. 2F – which also promptly got cancelled. A vehicle for comedy duo the Sklar Brothers, Apt. 2F didn’t last long, but it gave Galifianakis and fellow future stars Amy Poehler and Stephen Colbert some early exposure. A short clip from the show recently surfaced online, featuring the young Galifianakis full of vigor (and shorn of beard).

Around the turn of the century, Galfianakis had a smattering of bit parts in movies that could generously be called forgettable. (See, for example, Corky Romano. Actually, on second thought – do not see Corky Romano.) With Out Cold, though, he took on a slightly bigger part, one which prefigured the “oddball friend” role he would later perfect. Rather than say that Zach steals this goofy snowboarding movie, a more accurate way of putting it would be that a goofy snowboarding movie appears to be occurring alongside a better movie starring his character.

Galifianakis’ first chance to appear center stage arrived with the VH1 talk show/sketch show hybrid Late World with Zach. Like his other early TV work, Late World was swiftly cancelled; however, this show’s cancellation is largely considered to have been premature. In retrospect, the idea of having Galifianakis’ signature jokes-with-piano-accompaniment on the air five nights a week seems like a squandered opportunity. Cancellation looks to have been unavoidable, though, as Galifianakis has said: “I knew from day one when the VH1 guys came in and said, ‘Don't make fun of Cher, don't make fun of Sheryl Crow.’ Whatever their rotation was at the time. I was like, ‘Well, this isn't a good marriage.’”

Courtesy of FOX

Highlighting the journeyman aspect of Galifianakis’ acting career are the two seasons he spent as a main cast member on the hour-long drama, Tru Calling. Having one of the funniest guys around as comic relief should theoretically help a show’s chances, but it wasn’t enough to save this odd cross between Six Feet Under and Groundhog Day. Luckily, Zach spent his downtime from the show wisely, joining forces with a gang of like-minded comics for a unique stand-up tour that would significantly raise his profile.

In order to escape the purgatory of two-drink minimum Chuckle Huts, Patton Oswalt organized a groundbreaking tour of rock clubs with his “alt-comedy” friends: Brian Posehn, Maria Bamford, and Zach Galifianakis. With its smartass title doubling as a mission statement, The Comedians of Comedy tour spawned both a film and a TV series. In addition to the touring dynamic that the cameras were meant to capture, the series also documents Galifianakis in a transitional state of his stand-up career, as he cultivates the confrontational style he would soon unleash on larger audiences.

Although he was thriving as a stand-up by 2006, on television Galifianakis was beginning to look like the goose that laid the funny-but-cancelled eggs. Unfortunately, Dog Bites Man did nothing to change the ratio. The conceit of this clever, partially improvised Comedy Central show was that while its cast posed as reporters, they interacted with civilians who believed they were being filmed for the news. While it didn’t make it past nine episodes, Dog Bites Man has the distinction of being Galifianakis’ final show to get cancelled.

Not only is Live at The Purple Onion a paragon of what a great comedy concert film should be, it’s also a functional parody of one. The interstitial segments which introduce Galifianakis’ “brother” — the foppish Southerner, Seth — are conceptual comic set pieces that shed no actual light on the performer himself. Between impenetrable, stone-faced one-liners and (hopefully) fake stage tantrums, Galifianakis manages to remain an electric, if enigmatic presence.

There’s something undeniably hypnotic about watching Zach Galifianakis and indie folk star Will Oldham lip dub a Kanye West song from atop a tractor steadily rolling through the comedian's farm in rural North Carolina. Appearing in this viral video may not have directly impacted Galifianakis’ career, but it helped create the (accurate) impression that the multi-platform comic was starting to pop up everywhere.

Considering their mutual affinity for messing with people’s minds, it was perhaps inevitable that Galifianakis would collaborate with new-wave arbiters of the absurd Tim Heidecker and Eric Wareheim. Although he has appeared on both of Tim and Eric’s TV shows, the trio’s defining moment together has to be the series of ads they created for Absolut Vodka. Ostensibly commercials, these videos play just like Tim and Eric sketches whose shared punchline is the fact that Absolut Vodka is somehow actually sponsoring them. These ads symbolize how outsider comedians like Galifianakis are still able to push boundaries from within the mainstream.

The Funny or Die web series Between Two Ferns is Galifianakis’ hilarious response to a culture increasingly obsessed with celebrity. Each episode finds the host sitting across from a famous actor on an Inside the Actors' Studio-like spartan set, alternately fawning over and antagonizing them. The results are equal parts discomforting and drop-dead funny. Of course, it had to have been abundantly clear after the first couple editions of Between Two Ferns that with his next movie, Galifianakis was about become a huge celebrity in his own right.

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Usually it’s difficult to pinpoint the exact moment in a person’s career when he or she has truly arrived. With Galifianakis, it’s clear as day. The Hangover collected all the galvanic mojo the comedian had stirred up in the preceding years and exploded it on an unsuspecting public. When the smoke cleared, the “wolf pack speech” had instantly entered the pantheon of fratty quotables, Galifianakis’s naked ass was seared into the retinas of a grateful nation and a new comedy superstar was born.

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Although Galifianakis only briefly appears in Up in the Air briefly, his one-scene cameo is notable for three reasons: 1) he is terrific in it, 2) his performance is barely funny and 3) that’s by design. Tellingly, most of this single scene plays a prominent role in Up in the Air’s trailer, due in no small part to his sudden, precipitous rise in popularity.

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No parent in their right mind would subject a young child to watching The Hangover, although apparently the movie’s breakout star is cuddly enough for the stroller set. In 2009, Galifianakis headlined Disney’s guinea pig adventure, G-Force, and his voice will next be featured in the upcoming Shrek spinoff, Puss in Boots. It’s clear that the guy is doing what he can to make kids' movies safe for adults again.

Capping off a banner year in 2009, Zach Galifianakis co-starred in HBO’s neo-noir comedy series, Bored to Death, alongside Jason Schwartzman and Ted Danson. It’s a role he was born to play — the perennially stoned sidekick to Schwartzman’s wannabe private eye, spurring his buddy on to bad decisions and occasionally leading by faulty example. While Danson gets the lion’s share of choice lines here, Galifianakis gets to stretch ever so slightly and play a more nuanced character than usual. The show is currently filming its third season – and for once, there are no signs of cancellation looming.

“How to Steal a Funny Movie Away From Other Funny People,” by Zach Galifianakis. Step 1: Get cast in a good-not-great comedy like Dinner for Schmucks. Step 2: Stay out of the first half, letting the audience’s appetite build. Step 3: When you enter, effortlessly draw attention to yourself through sheer animal magnetism. Step 4: Repeat Step 3, only with a manic intensity one notch below demonic possession. Step 5: Go away again until the climax. Step 6: Allow yourself to be upstaged by the lead. Step 7: Go out with a bang.

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After stripping a diamond mine together once before, it was a no-brainer for Galifianakis to work with Hangover director Todd Phillips again — especially with Robert Downey Jr. on board. Unfortunately, the road comedy Due Date seems to suffer from the same problem as the Adam Sandler/Jack Nicholson team-up Anger Management – meaning nobody planned much beyond simply pairing the two leads together. While not quite a misstep (it made $100M), Due Date is Galifianakis’ only post-Hangover role so far that feels a little slight. It’s still a must-see, though, if for no other reason than the surreal spectacle of his character acting on an episode of Two and a Half Men.

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Very few episodes of any TV show last year felt more like an event than when Zach Galifianakis hosted Saturday Night Live for the first time. Here was comedy’s newest savior meeting its most venerable institution, and it was a long time coming. "I actually wrote for Saturday Night Live for two weeks 10 years ago,” Galifianakis has since said. “There was not one laugh the whole time I was there. It was like, 'What have I done?' Then they let me go." Apparently, sometimes you have to go away in order to come back. Even though playing the piano while telling jokes is one of the oldest arrows in Galifianakis’s quiver, it was still one of the freshest moments on SNL all year.

Fiona Apple isn't best known for her sense of humor, which may be part of why she teamed up with Galifianakis for this silly video for "Not About Love," a track from her 2005 album Extraordinary Machine. As Galifianakis lip-synchs the tune, Apple plays the straight man, looking on with sullen disdain as he emotes and strikes melodramatic poses.

They say there’s no such thing as a sure thing, but betting against the runaway success of The Hangover Part II would have been the ultimate sucker’s bet. Something of a victory lap for the first movie, and also a remix of it, The Hangover Part II feels familiar indeed. The good news is that Zach Galifianakis can still get laughs by wringing every last bit of weirdness from a Long John Silver’s punchline. The even better news is that this movie’s wild success ensures he’ll be able to write his own ticket for the foreseeable future.

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Munawar Hosain/Fotos International/Getty Images (Zach), Neilson Barnard/Getty Images for The Muppets Studio (Kermit)

Galifianakis is set to make a brief appearance as "Hobo Joe" in Jason Segel's reboot of The Muppets. This makes a lot of sense, at least in that Galifianakis sometimes comes across like a living, breathing Muppet and so it seems totally natural for him to share a movie screen with Kermit the Frog.

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• Review: The Hangover Part II

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