Chamberlain made his film debut in The Secret of the Purple Leaf (1960), a crime drama set in the Caribbean. He agreed to exploit Kildare's image by playing a young doctor in “Morning Joy” (1965), a lightweight drama about newlyweds, along with Yvette Mimew. It did not require any particularly complex properties (or aggressively). However, he gave some memorable and, at the time, a surprising film performance.
They include Julie Christie's dangerous husband in Petulia (1968), Octavius in Julius Caesar (1970), Tchaikovsky in Music Enthusiast (1971), Aramis in Three Musketeers (1973), and its sequel, Countering inigrno by the disable in imserno by the wardly electricengeer in the widely electric engener (1974). Aboriginal culture in Peter Weir's drama The Last Wave (1977).
His stage career got off to an unfortunate start with the disastrous 1966 Broadway musical adaptation of “Tiffany's Breakfast,” starring Mary Tyler Moore, which was also closed in preview. However, he later praised the classic roles of “Richard II” and “Cylano de Bergerac”, and “Hamlet”. In the 1970s he was nominated for the Drama Desk Award twice for his portrayal of a fallen pastor in Williams, Tennessee's Night of Iguanas (1976), and for his portrayal of Bill Hickoc (1976) in the wild in the public theaters, Father and Son (1978). He called Hickok his favorite role.
He returned to Broadway, but succeeding “Blithe Spirit” (1987) and “My Fair Lady” (1993) and “The Sound of Music” (1999) at least, if not more than a respectful review. (The musical reminded longtime fans that it had a record of hits singing the theme of “Dr. Kildare” in the '60s.)
In addition to the miniseries, he appeared in numerous films for television, playing the title roles in “F. Scott Fitzgerald and The Last of the Bells” (1974) and “The Man in the Iron Mask” (1977). He appeared in another series, Island Son, in 1989, playing yet another doctor, but he was unhappy in that direction and lasted only one season.
After his formal appearance, Chamberlain appeared to be happy to portray characters who were either gay or played with gender stereotypes. He had already completely dragged as a female character and appeared on the sitcom The Drew Carey Show. He was a guest star for “Will & Grace” and made a cameo appearance in the film “I Now You Chuck & Larry” (2007).
