"Deep, Deep Trouble" is a rap song from the 1990 Simpsons album The Simpsons Sing the Blues, performed 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 in late 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, with its humorous lyrics and Cartwright's performance being singled out for praise.
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