Sherwood began his acting career on stage and started in musical theatre in Montreal starting in 1975. He starred in such stage musicals as Ain't Misbehavin', Cabaret, and The Music Man. He began acting in several Canadian and American feature films starting in 1979. In 1986, he joined the cast of the American television series, Airwolf II, playing the role of Jason Locke. In 1989, Sherwood won the role of Dillon Beck in the CBC Television series, Street Legal. He portrayed this role on Street Legal from 1989–1994 and was nominated in 1992 for a Gemini Award Best Performance by an Actor in a Supporting Role. He has guest-starred in a variety of television shows including: Beauty & The Beast, Single Ladies, Lost Girl, The Art of More, The Listener, Aaron Stone, Being Erica, Due South, Outer Limits, Soul Food, Earth: Final Conflict, PSI Factor, 1-800 Missing, Danger Bay, Adventure Inc., Diamonds, Alfred Hitchcock Presents, Night Heat, The Best Years, Ghost Writer and Counter Strike.