"Crossroad Blues" was a song written in the "blues" musical style on Earth in the early 20th century.

Sonek Pran played a recording of this song during an evening he spent with longtime friend Rupi Yee. They began to kiss during the song, marking the beginning of a romantic relationship which eventually led to marriage. At Yee's funeral in 2381, Pran played the song in her honor on his banjo.

Pran also earlier suggested "Crossroad Blues" during an impromptu concert aboard the USS Aventine while en route to the Imperial Romulan State. Ensign Erin Constantino was also familiar with the song, though the other musicians were able to "fake it". (ST novel: A Singular Destiny)