Bill Monroe wrote “My Rose of Old Kentucky” and recorded it with his Blue Grass Boys on 27 October 1947 at the WBBM radio studio in Chicago. Monroe sings it alone, without the duet or trio harmony heard on much of the band’s work from the period, and plays mandolin. Lester Flatt is on guitar, Earl Scruggs on banjo, Chubby Wise on fiddle and Howard Watts, billed as Cedric Rainwater, on bass. Columbia released it on 12 April 1948 as the A-side of Columbia 38172 (also issued as 20423). On the B-side was “Sweetheart You Done Me Wrong,” another Monroe song, sung by Flatt with Monroe on tenor.
The rose is a girl. She bloomed for him in a cabin on a hill in a little village, they vowed to love each other, and he is sure they always will. In the chorus he watches her bloom as the years roll by and swears there will never be another; he will love her until he dies. Later verses find him dreaming of her in a gingham dress and longing for Kentucky and his darling. The closing verse answers the listener who wonders why he is so sure: she is his rose of old Kentucky, and she will never lie.
Rose Maddox recorded the song in Nashville on 19 March 1962, with Monroe himself on mandolin, Don Reno on banjo and Red Smiley on guitar, for Rose Maddox Sings Bluegrass (Capitol, November 1962). Doc Watson included it on his double album Memories (United Artists, 1975). The Osborne Brothers recorded it in 1978 at Hilltop Studios in Nashville for Bluegrass Collection (CMH), with Kenny Baker and Blaine Sprouse on fiddles. Ralph Stanley recorded it at Maggard Sound Studio in Big Stone Gap, Virginia, on 15 December 1989, with Curly Ray Cline on fiddle and Jack Cooke on bass, for Like Father, Like Son (Copper Creek). Later versions include the Del McCoury Band’s on Old Memories: The Songs of Bill Monroe (2011), sung by Del McCoury, and Darin & Brooke Aldridge’s on Snapshots (Mountain Home, 2015).