Bob Dylan

While Bob Dylan was in his 10th grade, his back-up band was rejected from a high school talent show because the student council judged his performance at the audition too shocking.

Finally, when his talent received recognition and he was about to sign his first contract with Columbia Records, Dylan conned his way out of a stipulation that required his parents to sign the contract -- as Dylan at 20, was considered a minor at the time -- by convincing John Hammond that he was an orphan.