"Deep, Deep Trouble" is a rap song from the 1990 Simpsons album The Simpsons Sing the Blues, sung by the fictional character Bart Simpson (voiced by Nancy Cartwright) about his trouble-making antics. It was written by Matt Groening and DJ Jazzy Jeff and recorded during the fall of 1990. The song was released as the second single from the album in early 1991 and an accompanying music video (directed by Gregg Vanzo) was broadcast on television on March 7, 1991. This video has since been released on DVD as part of the 2002 boxset The Simpsons: The Complete Second Season. "Deep, Deep Trouble" charted in several countries around the world, including the top ten in Ireland, New Zealand, and the United Kingdom. Critical reception of the song was positive and it has been praised for its humorous lyrics.

"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".

The song is a rap performed by the character Bart Simpson about his trouble-making antics. Groening has described it as "the tragic story of Bart Simpson, a bad youth gone worse."The Simpsons cast member Nancy Cartwright, who voices Bart on the show, provided the character's voice in "Deep, Deep Trouble" as well. The characters Homer Simpson and Maggie Simpson are also featured, with Homer ranting at Bart, and Maggie sucking on her pacifier to the beat of the song.

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