“There’s More Pretty Girls Than One” is the song of a rambler who leaves a sweetheart behind and consoles himself that any town he roams through has more pretty girls than one. His mother told him only the night before to give up rambling and marry a good wife. Instead he tells the girl he is leaving to look down the lonesome road, hang her head and cry, while his own thoughts run to the other pretty girls.
The earliest record listed by SecondHandSongs was made on 11 April 1929 by the Kentucky fiddler Leonard Rutherford and the singer and guitarist John D. Foster. It was issued in 1930 under the pseudonym Crocker and Cannon. The Arthur Smith Trio, made up of the fiddler Arthur Smith with Alton and Rabon Delmore on guitars, all three singing, recorded it at the Hotel Charlotte in Charlotte, North Carolina, on 17 February 1936, and Bluebird issued it that April on B-6322, backed with “Chitlin’ Cookin’ Time in Cheatham County.” The trio followed it on 26 January 1938 with “The Answer to More Pretty Girls Than One,” issued on Bluebird B-7437 that March. Riley Puckett and Red Jones recorded the song in September 1937. Writer credits differ. SecondHandSongs and some later releases list it as traditional, while the 1973 RCA album by Lester Flatt and Mac Wiseman credits Arthur Smith and Alton Delmore.
Country and bluegrass singers kept returning to it. Webb Pierce recorded it in December 1960. Jimmy Martin and the Sunny Mountain Boys cut it in Nashville on 12 February 1964 for Sing Widow Maker (Decca, 1964). Mac Wiseman recorded it in Akron, Ohio, in April 1966 for Sings Old Time Country Favorites (Rural Rhythm, 1967), and Doc Watson on 14 December 1971 for Elementary Doctor Watson (Poppy, 1972). Flatt and Wiseman sang it as a duet at RCA’s Nashville studio on 5 July 1973 for Over the Hills to the Poorhouse, with Marty Stuart among the backing musicians. Ricky Skaggs and Tony Rice recorded it as a mandolin-and-guitar duet for Skaggs & Rice (Sugar Hill, 1980), with Rice singing lead and Skaggs harmony. In 1998 Wiseman sang it again with Doc Watson and Del McCoury on Mac, Doc & Del.