Early work
Galifianakis moved to New York City with college friend and future Late Night with Jimmy Fallon head writer A.D. Miles. Following his television debut on Boston Common, Galifianakis joined Saturday Night Live for two weeks. He has stated "I worked on Saturday Night Live for two weeks, and Britney Spears was the host one week when I was doing it. Wrote a sketch, Will Ferrell was going to play a bodyguard to her belly-button, and we were going to shrink Will down to fit into a belly-button. ...she just stared at me after I explained it to her. And then, she finally goes 'Yeah, that's funny.'" Galifianakis co-starred in the film Out Cold, and had small roles in Corky Romano, Below, Bubble Boy, Heartbreakers, Into the Wild, Super High Me, Little Fish Strange Pond and Largo.
In September 2001, he appeared in an episode of Comedy Central Presents. It included a stand-up routine, a segment with a piano, and a cappella group The Night Owls (introduced as his "12 ex-girlfriends") singing "Eternal Flame" by The Bangles while he made jokes. In 2002, he hosted his own VH1 talk show called Late World with Zach. It featured many of his friends and regular performers from the Los Angeles comedy and music venue Largo where he appeared frequently during this time period. He played Davis in the Fox drama series Tru Calling. He appeared many times on Jimmy Kimmel Live! and played Frisbee in Reno 911!
Galifianakis played Alan Finger on the Comedy Central show Dog Bites Man, a fake news program that caught people during candid moments thinking they were being interviewed by a real news crew. He also guest-starred in the episode of the Comedy Central show The Sarah Silverman Program as Fred the Homeless Guy. He also had a recurring guest role as a doctor on the animated Adult Swim show Tom Goes to the Mayor and appeared in several episodes of Tim and Eric Awesome Show, Great Job! in a recurring role as Tairy Greene.
In 2006, Galifianakis appeared in Fiona Apple's music video for the song "Not About Love", where he is seen lip-synching the lyrics to the song. A year later, Kanye West employed Galifianakis and indie rock musician Will Oldham for similar purposes in the second version of the video for his song "Can't Tell Me Nothing". In June 2006, Galifianakis released the single "Come On and Get It (Up in 'Dem Guts)", a comedic hip-hop dance song which features Apple's vocals.
Galifianakis, Patton Oswalt, Brian Posehn and Maria Bamford, are the four Comedians of Comedy, a periodic packaged comedy tour in the style of The Original Kings of Comedy and the Blue Collar Comedy Tour. They chose to perform at live rock clubs as opposed to comedy clubs to try to reach a different audience. Much of the tour was taped and has been featured in both a short-lived TV series on Comedy Central and a full-length film that has appeared at SXSW and on Showtime. On February 22, 2008, he made an appearance on the Jackassworld.com: 24 Hour Takeover. He interviewed various members of the Jackass cast. Galifianakis starred in first leading role in the independent film Visioneers which premiered in 2008. The film was released on direct-to-DVD. That same year, Galifianakis appeared in a web video series of advertisements for Absolut vodka, along with Tim Heidecker and Eric Wareheim, creating a parody of the Golden Girls in which one has a deep anger issue, breaking the fourth wall in exasperation and outright violence on the set. He also completed the pilot Speed Freaks for Comedy Central.
His 2006 stand-up concert film Zach Galifianakis Live at the Purple Onion was one of the first original programs from Netflix.
