Bennett was a founding member of Titanic Love Affair. The band recorded three albums in the 1990s: Titanic Love Affair (1991), No Charisma (1992), and Their Titanic Majesty's Request (1996). He also played guitar with Steve Pride and His Blood Kin and Gator Alley. Nearing a master's degree in education at the University of Illinois, Bennett became a classroom teacher at Urbana Junior High, first as a substitute in 1985. Bennett was a full-time middle-school math teacher in 1986 at the then redesignated Urbana Middle School. He also worked for several years as an electronics technician for a local audio-video repair store.