The Second Time Around is a 1960 song with lyrics by Sammy Cahn and music by Jimmy Van Heusen. It was introduced in the film High Time, sung by Bing Crosby with Henry Mancini conducting, and was nominated for the Academy Award for Best Original Song but lost to Never on Sunday. Crosby recorded it on August 25, 1960 for MGM Records, but the tune is especially associated with Frank Sinatra, who recorded it for Reprise Records on December 21, 1960. Sinatra's version reached number 50 on the Billboard Hot 100, and he re recorded it in 1961 and 1963. The song has become a standard and has been covered by many artists including Peggy Lee, Shirley Bassey, Sarah Vaughan and Andy Williams; it appears on Sinatra's Sinatra album from 1963.
