The only son of a banker father and radio personality mother, Winters spent a difficult childhood shuttling between his divorced parents. By his own descriptions, his alcoholic father could be monstrous and his mother tended to want the spotlight focused on her. In order to escape, Winters enlisted in the US Marines at age 17 and spent over two years serving in the South Pacific. After WWII, he enrolled at Kenyon College and then transferred to the Dayton Art Institute. At the suggestion of his wife, he began his entertainment career by entering a talent contest where he wowed the audience and walked away with a gig as a disc jockey which in turn led to a stint as a local TV personality. In the early 1950s, Winters moved to NYC where he could better exploit his comedic talents. He shone in local comedy clubs and early live TV where his expressive, moon-shaped face and abilities for zany mimicry and adept characterizations became increasingly popular. In 1954, Winters was cast as a regular on the comedy-variety series "And Here's the Show" (NBC, 1954) and went on to become nearly a permanent fixture on many TV shows that propelled his antics (which included characters like the ribald old lady Maude Frickert and the quack psychiatrist Dr. Bellenhoffer) into unsuspecting American living rooms. From the mid-50s on, he was showcased in over ten comedy specials and series with his name attached (e.g., "The Jonathan Winters Special", NBC 1964; "The Jonathan Winters Show", CBS 1967-69) and appeared in dozens of comedy programs hosted by fellow comedians Bob Hope, Dean Martin and Steve Allen. His career was unaccountably shadowed, however, by two highly publicized nervous breakdowns, the result of an undiagnosed bipolar disorder exacerbated by alcohol and caffeine. Since the early 1960s, Winters has been on lithium and has not suffered any manic-depressive episodes. Yet, because he was one of the first celebrities to "go public" with his problems, he was stigmatized and even some 40 years later his "problems" are still mentioned in articles and profiles.

Though less prolific on the big screen, Winters appeared in several memorable 60s films including Stanley Kramer's star-studded mess "It's a Mad, Mad, Mad, Mad World" (1963), Tony Richardson's black comedy "The Loved One" (1965, as twins) and Norman Jewison's "The Russians Are Coming, the Russians Are Coming" (1966, as a deputy). His later output often wasted his gifts, although he made the most of the opportunities afforded in "Moon Over Parador" (1988), "The Shadow" (1994) and "The Adventures of Rocky and Bullwinkle" (2000).

Though he diversified into other mediums (e.g., books, films and albums), TV provided Winters with his greatest exposure and opportunities. Younger audiences may remember him as the son of Mork (Robin Williams) on "Mork and Mindy" during the final season (1981-82) of that popular sitcom. This was an apt (if perversely role reversed) casting choice for a father and son team in light of Williams' status as the heir apparent to Winters' free associative, agile-brained humor. A versatile vocal performer, Winters has also provided voices for many children's cartoons including "The Smurfs" (as Papa Smurf), "Yogi's Treasure Hunt" and "The Completely Mental Misadventures of Ed Grimley". He finally received long overdue formal recognition from his peers with an Emmy award for his role as Randy Quaid's gruff father on the short-lived sitcom "Davis Rules" (ABC, 1991; CBS 1991-92), induction into the Comedy Hall of Fame alongside such other luminaries as Milton Berle, George Burns and Walter Matthau and the receipt of the second annual Mark Twain Prize in Humor.