Born Walden Robert Cassotto in East Harlem, New York City, he allegedly chose his stage name from a neon Chinese restaurant sign with the "Man" burned out of "Mandarin." Another story has him flipping through a phone book and finding the name Darin.
Since childhood, he was plagued by a heart condition caused by rheumatic fever. The threat of an early death pushed him to pursue his dream of becoming "a legend by age 25."
He started his music career as a songwriter with Don Kirshner. The pair wrote songs for an up-and-coming artist named Connie Franconero (aka Connie Francis). Bobby and Connie started dating and even planned to elope until her strict father found out: He chased Bobby at gunpoint out of his daughter's life.
His first hit was the 1958 rock 'n' roll novelty tune "Splish Splash
," which made him a teen idol at 22. Just one year later, he transformed into a suave nightclub entertainer with his swinging rendition of "Mack The Knife
." The song won him two Grammy awards for Best New Artist and Record of the Year.
In 1960, he starred in the romantic comedy Come September, and met popular teen actress Sandra Dee. They married shortly after and welcomed a son, Dodd, the following year. (They divorced in 1967.)
In his early '30s, he was devastated to learn that the woman who he thought was his mother was actually his grandmother and his older sister, Nina, was indeed his biological mother. Nina was facing the scandal of becoming an unwed teen mother, so the women concocted the story to protect her reputation.
He worked on his friend Robert Kennedy's presidential campaign in the '60s, and was at the Ambassador Hotel in Los Angeles when Kennedy was assassinated there in 1968. Shattered by the loss, Bobby was drawn to more serious subject matters and began singing protest songs under the name "Bob Darin." Fans who showed up in Vegas to hear the "Mack the Knife" singer were shocked to see him without his toupee, wearing blue jeans instead of his signature tux. They booed him off the stage.
Kevin Spacey, an admitted Bobby Darin fanatic, starred as Darin in the 2004 biopic Beyond the Sea
(named after the hit song
). Aside from co-writing and directing the film, he also did most of his own singing.
In 1994, Dodd Darin published a book about his famous parents, Dream Lovers: The Magnificent Shattered Lives of Bobby Darin and Sandra Dee.
He was nominated for an Academy Award for Best Supporting Actor for his role as a shell-shocked soldier in the 1963 film Captain Newman, M.D.
In 1971, he had artificial valves implanted in his heart, but his health continued to falter. After failing to take antibiotics to prevent infection after a dental procedure, he developed sepsis and further weakened his heart. Shortly after undergoing surgery to prepare the damage, he died at age 37.