"The Second Time Around" is a song with words by Sammy Cahn and music by Jimmy Van Heusen. It was introduced in the 1960 film High Time, sung by Bing Crosby with Henry Mancini conducting his orchestra, and was nominated for the Academy Award for Best Original Song. It lost out to "Never on Sunday".
Its theme is captured by its first two lines:
Although Crosby recorded it on August 25, 1960, for MGM Records, it is especially associated with Frank Sinatra, who recorded it for Reprise Records on December 21, 1960. This achieved some chart success reaching the #50 position in the Billboard Hot 100 chart. Sinatra also recorded it again for Reprise on November 5, 1961, and April 29, 1963.
Jane Morgan sang the song on a 1961 episode of The Jack Benny Program.
Dame Kiri Te Kanawa performed this with André Previn on Kiri Sidetracks: The Jazz Album (1992).
Recorded versions
Basin Street East Proudly Presents Miss Peggy Lee, Peggy Lee, 1961
Let's Face the Music, Shirley Bassey, 1962
This Time It's Love, The Hi-Lo's, 1962
You're Mine You, Sarah Vaughan, 1962
Moon River and Other Great Movie Themes, Andy Williams, 1962
Love Letters, Julie London, 1962
Ahmad Jamal at the Blackhawk, Ahmad Jamal, 1962
Hollywood – My Way, Nancy Wilson, 1963
Make Mine Swedish Style, Monica Zetterlund & Bill McGuffie Quartet, 1964
More 4 Freshmen and 5 Trombones, The Four Freshmen, 1964
Ellington '65, Duke Ellington, 1965
Loads of Love, Shirley Horn, 1965
Shirley Bassey at the Pigalle, Shirley Bassey, 1965
That's All, Mel Tormé, 1965
The Movie Song Album, Tony Bennett, 1966
The Dealer, Chico Hamilton, 1966
Woman Talk, Cleo Laine, 1966
Grandes Exitos del Cine de los Años 60, Connie Francis, 1967
Dusty... Definitely, Dusty Springfield, 1968
Quintessence, Bill Evans, 1976
It Only Happens Every Time, Monica Zetterlund & The Thad Jones / Mel Lewis Orchestra, 1977 Rosemary Clooney Sings the Music of Jimmy Van Heusen, Rosemary Clooney, 1986 Pop Pop, Rickie Lee Jones, 1993 Manilow Sings Sinatra, Barry Manilow, 1998 Romance on Film, Romance on Broadway, Michael Feinstein, 2000 The Movie Album, Barbra Streisand, 2003 Bolton Swings Sinatra, Michael Bolton, 2006 Ballads from the Midnight Hotel, Todd Gordon (2007) Late in Life, Sue Raney, 2015