Winter was born in Ventura, California, and began his career on Broadway. Winter was twice nominated for Tony Awards as Best Supporting or Featured Actor (Musical). The first was in 1967, as Herr Ludwig in Cabaret, then in 1969, as J.D. Sheldrake in Promises, Promises.
He moved on to television, appearing on the daytime serials The Secret Storm and Somerset.
He was cast on M*A*S*H as Lt. Col. (later Col.) Flagg, becoming one of the program's more memorable and popular recurring characters; he appeared in seven episodes as Flagg during the show's 11-year run. Before his introduction as Flagg, Winter had also appeared on the series as Captain Halloran. A number of fans have expressed the belief that Captain Halloran might have been one of Flagg's many aliases, especially as he said to Dr. Freedman, "we played poker once," which Captain Halloran had.
Winter was also a recurring character on the primetime 1970s sitcom Soap, portraying Congressman Walter McCallum, who was in a relationship with Chester and Jessica Tate's daughter Eunice.
In 1977, Winter appeared in an episode of Lou Grant titled "Housewarming" as a reporter who beat his wife. The same year, he appeared in "Never Con a Killer," the pilot for the ABC crime drama The Feather and Father Gang.
Winter guest-starred in season one The A-Team, in "Holiday in the Hills" and appeared in the season 5 episode "Road Games."
He also starred in the NBC primetime drama Project UFO in 1979 and was featured in the film A Change of Seasons. He appeared as the corrupt county commissioner Bob Gebhardt in the 1983 movie Porky's II: The Next Day and in From the Hip, also directed by Porkys director Bob Clark.
Winter guest-starred in The Golden Girls as a blind man who goes out with Blanche, whom she does not want to go out with because he is blind, in the episode "Blind Date". In 1985 he guest-starred as Capt. Hennessey in Episode 14, Season 4, of Cagney & Lacey.
Winter co-starred in the 1986 TV movie A Christmas Gift with John Denver as the character Thomas Renfield. Three years later, he portrayed Las Vegas entertainer Johnny Roman in Mike Hammer: Murder Takes All. Roman was the first character in that television film to lose his life due to a mysterious murder.
Winter appeared on a 1991 episode of the television series Night Court as Clarence Egan.
Winter also had a recurring role on the FOX sitcom Herman's Head from 1991 - 1994. Winter portrayed Mr. Crawford, an executive at Waterton Publishing, where the series lead character Herman Brooks (William Ragsdale) worked.
He appeared in the 1995 Seinfeld episode "The Beard" playing Robert's boss. Winter was featured as the real-life character of Carl Lawson in a 1995 episode of UPN's Real Ghosts aka Haunted Lives: True Ghost Stories.
He has also done voices in animation including six television programs: The Real Adventures of Jonny Quest, Duckman, Aaahh!!! Real Monsters, The Angry Beavers, Fantastic Max, Paddington Bear, and the animated film Adventures in Odyssey: Shadow of a Doubt.
Winter died in Woodland Hills, California, of complications from Parkinson's disease. His ashes were scattered into the Pacific Ocean.
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