Mason has toured extensively throughout the US and Europe with Schwervon! and as a solo performer, often supporting members of the antifolk movement, such as Jeffrey Lewis or affiliated bands (Misty's Big Adventure).
He first came to prominence as a solo performer in the 1990s in New York as one of a group of musicians and songwriters (including Lach, Jeffrey Lewis, Curtis Eller, The Burning Hell, Dibs, Boo Hoo and Beck) who made up the antifolk movement based around the Sidewalk Cafe on the Lower East Side of Manhattan.