Early Career
Galifianakis' career began on television in 1996, when he played the recurring role of a stoner named Deuce in the short-lived sitcom Boston Common. Then he joined Saturday Night Live as a writer but lasted only two weeks. 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.
He had his own episode of Comedy Central Presents, which first aired in September 2001. It included a stand-up routine and a segment with a piano, and concluded with an 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 was the host of his own VH1 talk show called Late World with Zach. It featured many of his friends and regular performers from the LA comedy and music venue Largo where he appeared frequently during this time period. One episode featured Largo regulars Jon Brion and Rhett Miller as musical guests. His next television role was as a coroner named Davis in the Fox drama Tru Calling, which lasted from 2003 to 2005. He has also appeared many times on Jimmy Kimmel Live! and has made three appearances on Reno 911! as "Frisbee".
Galifianakis starred as 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. In addition, he was on an 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 was featured 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 rap/hip-hop/dance song which features Apple's vocals.
Galifianakis was, together with Patton Oswalt, Brian Posehn, and Maria Bamford, one of 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 movie 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 the independent film Visioneers which played in select cities in 2008. This was Galifianakis's first starring role in a film and was given a direct-to-DVD release. 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.
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