Formed in 1977, Doug & the Slugs have withstood numerous personnel changes. The original band, featuring guitarist John Burton, bassist Dennis Henderson, keyboardist Drew Neville, and drummers John "Wally" Watson and Ted Laturnus, was only together for a few months. By 1978, only Bennett, Burton, and Watson remained, with guitarist Richard Baker, bassist Steve Bosley, and keyboards player Richard Kendall replacing Henderson, Neville, and Laturnus. Although this lineup remained intact for a decade, the group continued to evolve. By the spring of 1998, the group featured Bennett, keyboardist/vocalist Marc Gladstone, drummer/vocalist Chris Murray Driver, guitarist/vocalist Elio Martelli, and bassist/vocalist Jay Wittur.

Signed by RCA after releasing a self-produced single, "Too Bad," in June 1980, Doug & the Slugs went on to record several impressive albums in the 1980s and early '90s. Their second album, Wrap It!, released in November 1981, featured the vocal harmonies of Toronto-based a cappella group the Nylons. Their third effort, Music for the Hard of Thinking, released in 1983, included the Canadian hit "Making It Work." Popaganda, released in 1985, received a Canadian Academy of Arts and Sciences award for Album of the Year and earned the band an award as Group of the Year.

Releasing the solo album Animato in 1986, Bennett has continued to balance group activities with work as a soloist. Making his theatrical debut in John Gray's musical Rock and Roll, he went on to co-produce an English translation of the long-running Quebec hit comedy Brew in 1993. Bennett has continued to establish himself as a writer, director, and producer of music videos. In addition to creating videos for Doug & the Slugs and Canadian rock bands Trooper, Headpins, Zappacosta, and Images in Vogue, he's worked with Canadian country music artists including Suzanne Gitzi, Rhodes & Marshall and Wyona Sue & the Turnpikes.