Known for single-handedly saving Frank Sinatra's career in the mid-1950s with his stunning orchestral arrangements, Riddle's "intelligent, seductive style" also attracted such singers as Nat King Cole, Ella Fitzgerald, Judy Garland, Johnny Mathis, and Linda Ronstadt. Peter Levinson, a friend of Riddle's, presents the musical side of Riddle as well as the private, including details of his marriage-ending affair with Rosemary Clooney.