10. Tiny Tim - 'Tiptoe Through the Tulips'
Many people remember Tiny Tim as the high-pitched weirdo who sang old songs on the ukelele on The Tonight Show and Laugh-In during the 1960s, but the man was also a very serious student of folk music. “No one knew more about old music than Tiny Tim," Bob Dylan said on his Sirius/XM radio show Theme Time Radio Hour. "He studied it and he loved it. He knew all the old songs that only existed as sheet music.” The pair hung out together during Dylan's early days in Greenwich Village, often performing at the same clubs.
In 1968, Tiny Tim became nationally famous when he appeared on The Tonight Show and performed "Tiptoe Through the Tulips," which originally charted back in 1929. His strange voice and demeanor made him a big hit with Carson, and he became a regular on the program. His fame peaked in 1969 when he married his 17-year-old girlfriend, Miss Vicki, on The Tonight Show. He died of a heart attack in 1996.