In the early eighties, he relocated to Chicago where he played various musical instruments in several bands including Savage Beliefs. He joined Big Black playing bass guitar in 1984. The following year, he produced and played saxophone on the Ward EP by End Result. In 1990, he played bass, piano, and percussion on the Algebra Suicide album Alpha Cue.
In 1993, he endured a stroke from which he has largely recovered, with his cognitive processes fully intact. Rumors of a failed suicide attempt are untrue; there is a history of early stroke on his mother's side of his family. Subsequently, Riley maintained an online journal under the pseudonym Paco Steinway, that outlined his experiences.