He performed in punk and noise bands in East Texas and was part of an avant-garde music scene in
Nacogdoches, Texas, before moving to
Austin, Texas, in 1999. In 2000, he began performing each week at coffee shops, public parks, and hotel rooms in Austin. In 2001, he moved briefly to
Berlin, Germany, and then to
New York City. From 2001 to 2005, he performed at the downtown theaters
Surf Reality and
Collective:Unconscious. He was named "Mr. Lower East Side" in 2003. In 2005, he had a weekly show at the Apocalypse Lounge bar, where he debuted
The Lionel Richie Opera.
The Lionel Richie Oper was the first of what became a seven-show series of performances, each built around a different pop star. In 2004, he co-starred with
Karen Finley for a theatrical run and subsequent tour of
George and Martha, in which he played
George W. Bush to Finley's
Martha Stewart. In 2005, Medlyn became a regular in the show Automatic Vaudeville at
Ars Nova, performing alongside VIDS,
Lin-Manuel Miranda, and
Billy Eichner, and the show hosts,
Bridget Everett and
Kenny Mellman. Medlyn was cast as a dancer by
Adrienne Truscott in
they will use the highways in 2000 and appeared in three dances choreographed by
David Neumann, including "feedforward". He designed sound for
Miguel Gutierrez (choreographer), winning a 2010
Bessie Award as part of the creative team for Gutierrez's "Last Meadow". ==The Neal Medlyn Experience Live==