“Little Glass of Wine” (also “The Little Glass of Wine”) is credited to Carter Stanley, but the melody is older. Ralph Stanley later recalled that as boys on Smith Ridge in the late 1930s the brothers heard a neighbor, Otto Taylor, sing a few verses of an old ballad he called “Poison in a Glass of Wine.” When the brothers needed songs for their show on WCYB in Bristol, Carter wrote new words to Taylor’s tune, and the song brought in so much mail that Jim Hobart Stanton decided to record them.
The story is a murder-suicide. A young man asks his sweetheart to marry him and she asks him to wait a year. He watches her dancing in a bar, decides to kill her before another man can have her, and takes her a glass of wine with poison in it. She says the wine has gone to her head and asks him to take her home. He tells her that they have both drunk poison, and they fold their arms around each other and die.
The Stanley Brothers first recorded it at WOPI radio in Bristol in late 1947 or early 1948, for Rich-R-Tone: Carter Stanley sang lead and played guitar, Ralph sang tenor and played banjo, Pee Wee Lambert played mandolin and Leslie Keith fiddle, with no bass. Rich-R-Tone issued it as 423 on 17 April 1948, backed with “Little Maggie.” The local success of the song led to their signing with Columbia that October. They recorded it again on 1 March 1949 at Castle Studio in Nashville, with Bobby Sumner on fiddle and Jay Hughes on bass in place of Keith, and Columbia released it as 20590 on 20 June 1949, backed with “Let Me Be Your Friend.” It remained a regular at their live shows, and Ralph Stanley recorded it again for a Japan-only 1971 album called John Henry, on Reunion with George Shuffler and James King, and on Sings His Favorites Now and Then in 2004.