On January 26, 2003, the day of
Super Bowl XXXVII, Milonakis decided not to attend a friend's Super Bowl party and instead recorded a video titled "The Super Bowl Is Gay". He posted the video to the website AngryNakedPat.com, and within two weeks it went
viral. A writer for
ABC's new late-night show,
Jimmy Kimmel Live!, spotted it and got Milonakis on the program. At the time, Milonakis was working as a tech support staffer at a Manhattan accounting firm. Over the next few years, Milonakis would continue to make guest appearances on Kimmel's show. The talk show host eventually sent a DVD of Milonakis's clips to MTV2 executive producer Tony DiSanto, proposing what would eventually become
The Andy Milonakis Show. MTV greenlit the pilot in 2005: an "absurdist, surrealist nightmare that used random people as actors," combining sketches and man-on-the-street segments with celebrity guest appearances. It would run for three seasons. Milonakis first started rapping on
YouTube; his first song was called "The Andy Milonakis Rap". He was in
Three Loco, a group that also included rap artists
Dirt Nasty and
Riff Raff, but on September 26, 2014, he announced that the group had broken up. From 2014 to 2015, Milonakis hosted and starred in a cooking show called
Fat Prince on Munchies, a YouTube channel that is part of the
Vice network. In each episode, he and a changing cast of chefs combined cheap ingredients with expensive ingredients to make a unique meal. Throughout 2017 and 2018, Milonakis was heavily involved with
livestreamer Paul Denino, better known as
Ice Poseidon, appearing in his livestreams and associating with his CX Network. In 2022, Milonakis partnered with
Voiceverse, a
blockchain-based startup that marketed itself as offering
AI voice cloning technology in the form of
non-fungible tokens. ==Personal life==