"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.
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