 "Deep, Deep Trouble" appeared on the successful 1990 album The Simpsons Sing the Blues that features songs sung by the characters from the American animated television series The Simpsons. It was recorded along with the rest of the album during the fall of 1990, at which point the cast members of The Simpsons were also recording the second season of the series. The song was written by The Simpsons creator Matt Groening and DJ Jazzy Jeff, and produced by DJ Jazzy Jeff and John Boylan. DJ Jazzy Jeff provided the drum programming, keyboards, and scratches on "Deep, Deep Trouble".
