As a teenager, Guerrero was one of the prominent members of the Bones Brigade, Powell Peralta's professional skateboarding team that was successful during the 1980s. He was well known for his relaxed style of street skateboarding and his Bones Brigade footage was primarily filmed in his hometown of San Francisco—the videos "Future Primitive", "The Search for Animal Chin", "Public Domain", and "Ban This" all featured the street skateboarding of Guerrero. After riding for Powell Peralta, Guerrero and Jim Thiebaud, a hometown friend and Powell Peralta teammate, started the skateboarding company "Real".
After his success in the world of skateboarding, Guerrero decided to pursue his musical interests and was a member of the skate rock band Free Beer and the experimental group Jet Black Crayon; however, Guerrero's work as a solo artist has so far been the most commercially and critically successful. Guerrero's critically acclaimed albums, EPs, and singles incorporate various types of music, from rock, electronic, hip hop, and funk, to soul, and jazz.
The EA video game "Skate" has featured numerous unreleased compositions that were written and recorded by Guerrero.