"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 now as I wander, my thoughts ever stray...") and returned for too late, just as she was preparing for marriage. 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. It has been recorded by many artists, but the best-known versions are by Gene Autry, Bing Crosby, and Frank Sinatra (1953). Guy Lombardo had a top ten hit with the song in 1939.
Members of the Western Writers of America chose it as one of the Top 100 Western songs of all time.