Dugan was born in Wheaton, Illinois, the second of four sons of Marion, a housewife, and Charles Dugan, an insurance salesman. He graduated from Goodman School of Drama at the Art Institute of Chicago (now at DePaul University) and started his acting career in 1969 in New York City. He moved to Hollywood in 1972 and appeared in his first TV show, The Sixth Sense. Later, he played in the 1973 TV movie The Girl Most Likely to.... Other early film appearances include Night Call Nurses (1972), Night Moves (1975), Smile (1975), Harry and Walter Go to New York (1976) and Norman... Is That You? (1976). In 1979, he was cast as the time-displaced hero in Unidentified Flying Oddball, Disney's very loose adaptation of A Connecticut Yankee in King Arthur's Court. In 1981, he appeared in Joe Dante's adaptation of The Howling.
Dugan made guest appearances on several TV series during the 1970s including The Mod Squad, The Waltons, Cannon, Columbo, The Rockford Files, and Alice. He also appeared in the mini-series Rich Man, Poor Man, as well as two episodes of M*A*S*H and in 1978 starred in the short-lived series Richie Brockelman, Private Eye, a spin-off from The Rockford Files.
He took on a recurring role as an aspiring caped crusader who called himself "Captain Freedom" on Hill Street Blues. He also appeared on Empire (1984) and Shadow Chasers (1984). He played Walter Bishop, briefly the husband of Maddie Hayes (Cybill Shepherd) on Moonlighting. Dugan's other film credits of the 1980s include Water (1985), Can't Buy Me Love (1987), She's Having a Baby (1988), The New Adventures of Pippi Longstocking (1988) and Ron Howard's Parenthood (1989).

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