"Play, Ruby, Play" is a song written by Tony Brown and Troy Seals. It was originally recorded by Conway Twitty for his 1990 album House on Old Lonesome Road. It was later recorded by American country music artist Clinton Gregory. It was released in January 1992 as the first single from his album Freeborn Man. The song peaked at number 25 on the Billboard Hot Country Singles & Tracks chart and reached number 20 on the RPM Country Tracks chart in Canada.