Fleet briefly attended Australia's National Institute of Dramatic Art (NIDA), but he was kicked out after a year for poor performance.

[citation needed] He also appeared in the ABC TV police dramas Phoenix and Janus as well as playing guest roles in The Flying Doctors and Stingers.

[citation needed] In 1988, after a guest appearance in The Flying Doctors, Fleet took on the role of Dave Summers in the Australian soap Neighbours.

Fleet was often heard on Triple M's Get This radio program as a frequent guest co-host alongside Tony Martin, Ed Kavalee, and Richard Marsland.

[2] Fleet mentioned that the funds from this DVD were going towards financing the filming of his classic 1995 show Thai Die as a feature-length comedy special.

[4] In recent years he has appeared in Underbelly: Squizzy playing Richard Harris "Australia's most violent prisoner" and series one of Wolf Creek as the bikie Gundog.

[citation needed] In 2018, he wrote and starred in the modern adaptation of Macbeth, Signifying Nothing the second of his plays to win best theatre and critics choice awards st the Adelaide fringe.

[citation needed] In 2021, he co-wrote and acted in the play The Twins with his old school friend Ian Darling AO which opened at the 2021 Adelaide Fringe Festival and won the Mental Health Awareness Award.