In 1959 a cocky twenty-three-year-old Bobby Darin, flush with the success of “Mack the Knife,” revealed his ambition to Life reporter Shana Alexander: He merely wanted “to be a pop legend at 25.”

Darin’s exuberant, off the-cuff performance of “Mack the Knife,” produced by Ahmet Ertegun, did become the stuff of legend, but Darin could hardly have predicted the path his career would take. Bom in the Bronx in 19366 , Walden Robert Cassotto allegedly chose his stage name by thumbing through the telephone book. Although he had played several instruments as a child, Darin never seriously considered a musical career until after he enrolled at Hunter College, in Manhattan.

Forsaking the student life after a semester or two, he landed a gig as a songwriter for Don Kirshner’s Aldon Music and soon made the leap from writer to performer, cutting a few unsuccessful sides for Decca before signing with Atco/Atlantic.