Zach Galifianakis

After his television debut on Boston Common, Galifianakis joined Saturday Night Live for two weeks.[14] 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.'"[15] 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.

Galifianakis on Inside Joke in New York City in 2008.

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.[6] 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-syncing 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)",[16] 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.[17] 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.[18] 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.[19]

Zach Galifianakis interviewing Barack Obama for Between Two Ferns.

Galifianakis has a series of videos on the Funny or Die website titled Between Two Ferns With Zach Galifianakis where he conducts interviews with popular celebrities between two potted ferns. He has interviewed Jimmy Kimmel,[20] Michael Cera, Jon Hamm,[21] Natalie Portman,[22] Charlize Theron, Bradley Cooper, Carrot Top, Conan O'Brien, Andy Richter, Andy Dick, Ben Stiller, Steve Carell, Sean Penn, Bruce Willis, Tila Tequila, Jennifer Aniston, Will Ferrell, Samuel L. Jackson, Tobey Maguire, Arcade Fire, Justin Bieber, Brie Larson, David Letterman, former President Barack Obama, Hillary Clinton, Brad Pitt and Keanu Reeves.[23] His interview style consists of typical interview questions, bizarre non sequiturs, awkward product endorsements and sometimes inappropriate sexual questions and comments.[24] Galifianakis won the Primetime Emmy Award for Outstanding Short-Format Live-Action Entertainment Program as a producer of the show at the 66th Primetime Creative Arts Emmy Awards.[25]

Galifianakis played Alan Garner in the hit comedy The Hangover and earned the MTV Movie Award for the Best Comedic Performance.[26] He was also prominently advertised in subsequent films that featured him in supporting roles, such as G-Force, Youth in Revolt and Up in the Air.

Galifianakis starred in the HBO series Bored to Death and hosted Saturday Night Live on March 6, 2010 during the show's 35th season, during which he shaved his beard mid-show for a sketch, and closed the show wearing a fake one.[27] He hosted again on March 12, 2011 and shaved his head this time, in a Mr. T-like hairstyle, which was allegedly supposed to be used for a sketch that never aired due to time constraints.[28]

In 2010, he starred in several films, including Dinner for Schmucks, It's Kind of a Funny Story, and Due Date.[29] On October 29, 2010, while debating marijuana legalization on the show HBO's Real Time with Bill Maher, Galifianakis appeared to have smoked marijuana on live television;[30] host Bill Maher denied that it was real marijuana in an interview with Wolf Blitzer during an episode of The Situation Room. In 2011, he reprised his role for The Hangover Part II, which was set in Thailand[31] and voiced Humpty Dumpty in Puss in Boots. Galifianakis starred alongside Will Ferrell in Jay Roach's 2012 political comedy The Campaign.[32] He received critical praise for his performance in the 2014 film Birdman or (The Unexpected Virtue of Ignorance), in which he starred with Michael Keaton, Emma Stone and Edward Norton. In 2017, Galifianakis voiced The Joker in The Lego Batman Movie.[33] In February 2023, Galifianakis joined the live-action film adaptation of Lilo & Stitch as Jumba.[34]