South of the Border (1939 song) "South of the Border " is a popular song describing a trip to Mexico , written by Jimmy Kennedy and Michael Carr and published in 1939 for the film of the same name starring country star Gene Autry . In the lyrics, a man looks back with regret and pain for having lied to the woman he can't forget and returned far too late, to discover she had become a nun. The lyric is in juxtaposition with the music, which swings with syncopated joy. The song was a hit in 1939 for Shep Fields , vocal by Hal Derwin . Other successful recordings in 1939 were by Guy Lombardo , Gene Autry, Ambrose and Tony Martin . Frank Sinatra recorded the song on April 30 , 1953 for Capitol Records and it reached the Billboard charts with a top position of #18 in a 4-week stay. Members of the Western Writers of America chose it as one of the Top 100 Western songs of all time.Other notable recordings Al Bowlly recorded May 11 , 1939 Acker Bilk – included in the album Clarinet Moods Asleep at the Wheel , with vocals by George Strait , for their 2015 album Still the King - Celebrating the Music of Bob Wills and his Texas Playboys Bing Crosby included in his album Bing Crosby's Treasury - The Songs I Love Chris Isaak for his album Baja Sessions Chuck Berry – for the album Chuck Berry Dean Martin for his album Dino Latino Engelbert Humperdinck – for the album The Winding Road Fats Domino included in his album Here He Comes Again! Frankie Laine Gale Storm – issued as a single and also included in the album Gale Storm Sings Gene Merlino - for The Simpsons episode "Kamp Krusty" Herb Alpert for his album South of the Border Keely Smith for the album Keely Sings Sinatra Malcolm Vaughan – included in the EP Requests for Malcolm Vaughan Marty Robbins - released in his posthumous collection Under Western Skies , released in 1995. Mel Tormé – included in the album Patsy Cline – included in her album Showcase Don Mclean – included in his album Prime Time Patti Page – recorded for her album Let's Get Away from It All Perry Como recorded for his album We Get Letters Russ Conway – for his album Piano Requests Sam Cooke – included in his Cooke's Tour album The Shadows – for their album Out of the Shadows Slim Whitman – included in the album In Love the Whitman Way Willie Nelson – for his album What a Wonderful World and for his album ''Let's Face the Music and Dance
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