“Carolyn (The Teenage Queen)” was written by Wendy Smith, whose first name appears on songwriter credits as both Wendell and Wandell, and published by Trianon Publications. Smith recorded it with his band, credited on the label as the Windy Mt. Ramblers, with Willie Burroughs on guitar, Joe McKinney on banjo, Andy Stein on fiddle and George Williamson on bass. Fortune Records, the Detroit label founded by Jack and Devora Brown, released it in 1967 as the B-side of “The Pill” on Fortune 233.
The song is told by Carolyn’s husband. He was pushing thirty and she was in her teens when she loved him, but a few years after the wedding her love was gone; by the time he is pushing forty she is barely twenty-four and longing to be free, sure the pastures are greener somewhere else. She goes to town at night, and gossip reaches him that she is running around. He cleans his gun and tells her to go out and have a good time, because it is her last night of fun, then sits up past midnight waiting for her. Instead a man with a badge arrives: Carolyn has been killed in a wreck on the highway. Looking at her face, the singer says she has cheated him once again. Each night afterward he burns the midnight oil thinking of her in the ground, his mind growing weaker, still in love with the teenage queen.
The song came back into bluegrass in the mid-1990s. Union Springs recorded it at Doobie Shea Studios in Ferrum, Virginia, for Next Train Headed South (Copper Creek, 1995), and the Lonesome River Band included it on One Step Forward (Sugar Hill, 1996), with Aubrey Haynie on fiddle and Jerry Douglas on dobro alongside the band; Sugar Hill later put that track on the band’s Best of the Sugar Hill Years (2007). The Lonesome River Band recorded it again, with a different lineup, Sammy Shelor still on banjo, for Chronology, Vol. 3 (Rural Rhythm, 2012).