According to the Associated Press, Winters passed away Thursday night from natural causes in his Montecito, Calif. home.
After a stint in the Marines and time at the Dayton Art Institute, the groundbreaking comedian got his start in the late '40s thanks to a talent show that he entered at the urging of his wife, Eileen. After that, he became a disc jockey and radio personality before moving to New York to focus on stand-up comedy.
A favorite of late-night hosts including Jack Paar and Johnny Carson, Winters had a gift for impersonations, creating eccentric characters, and pulling funny faces. His best-known character was Maude Frickert, a seemingly-sweet old lady with an acid tongue:
"As a kid, I always wanted to be lots of things," Winters told U.S. News & World Report in 1988.. "I was a Walter Mitty type. I wanted to be in the French Foreign Legion, a detective, a doctor, a test pilot with a scarf, a fisherman who hauled in a tremendous marlin after a 12-hour fight."
He appeared in nearly 50 TV shows and movies -- most memorably in "It's a Mad, Mad, Mad, Mad World" with Spencer Tracy and Mickey Rooney, and "Mork & Mindy" as the title couple's child, Mearth.
Robin Williams was a big fan of Winters, saying, "The best stuff was before the cameras were on, when he was open and free to create. ... Jonathan would just blow the doors off."
Winters won an Emmy for "Davis Rules" in 1991, and took home two Grammys for his comedy album. He was also honored with the Kennedy Center's second Mark Twain Prize for Humor in 1999.
On his own, short-lived primetime variety show, he made history by using color videotape for the first time in broadcast television. Many credit him with creating the video stunt of appearing as two characters on the same screen.
Winters had his share of troubles, however. In 2000, he revealed that he had suffered from manic depression in the early '60s.
Through the good times and bad, though, Winters kept up his first love -- painting.
"I've done for the most part pretty much what I intended -- I ended up doing comedy, writing and painting," he told U.S. News. "I've had a ball. And as I get older, I just become an older kid."