Fisher died Wednesday at his home in Berkeley of complications from hip surgery, his daughter Tricia Leigh Fisher told the Associated Press.
Fisher's boyish good looks and natural charisma also helped him land roles on television shows and in such feature films as "Butterfield 8," "Nothing Lasts Forever" and "Bundle of Joy."
But he may be best remembered for his failed marriages to Debbie Reynolds, Elizabeth Taylor and Connie Stevens.
Fisher was born in Philadelphia on Aug. 10, 1928.
In 1950 he recorded his first hit, "Thinking of You." In 1951, he had his first million-seller, "Any Time."
His "golden sound," as Fisher described it in his 1999 memoir, "Been There, Done That," catapulted him "from the streets of Philadelphia to the White House. Harry Truman loved me. Ike loved me."
In 1955, Fisher married Reynolds — known as "America's Sweetheart." It didn't take long for their celebrated union to fall apart.
Fisher created a tabloid scandal in 1958 when he left Reynolds, then just 26, for Elizabeth Taylor.
The move, considered in Hollywood at the time to be one of the century's biggest scandals, helped torpedo Fisher's career and launch Taylor toward superstardom.
Fisher would later acknowledge that he had been battling what would become a years-long addiction to drugs, including methamphetamine and cocaine.
In 1962, he suffered a breakdown after the collapse of his marriage to Taylor, who then married Richard Burton.
A complete obituary will follow at latimes.com/obituaries and in Saturday's print edition of The Times.