The Second Time Around

Written for the 1960 Bing Crosby comedy High Time, this mature, unhurried love song earned Cahn and Van Heusen an Academy Award nomination. Crosby’s original recording was warmly received, but it was Sinatra’s 1961 recording that won the Grammy Award for Record of the Year — giving the song a remarkable double life under two of the twentieth century’s greatest voices.

Cahn’s lyric — wise, patient, and free of the urgency of first love — spoke to anyone who had loved and lost and found the courage to try again. Peggy Lee’s live Basin Street East version earned its own Grammy nomination; Hank Crawford’s soulful alto reading shows how naturally the song translates into jazz.