Deep, Deep Trouble

"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 September 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, peaking at number one in Ireland and entering the top 10 in 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.

"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 late 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 (voiced by Dan Castellaneta like on the show) ranting at Bart, and Maggie sucking on her pacifier to the beat of the song.

"Deep, Deep Trouble" was released in early 1991 as the second single from The Simpsons Sing the Blues after "Do the Bartman", which also features Bart rapping. That single achieved much popularity, charting highly on the singles charts in Australia, Ireland, New Zealand, Norway, and the United Kingdom, and eventually becoming certified gold in the latter country with 400,000 units sold.

"Alarm was buzzin', I was snoozin',
Supposed to get up now, but I was refusin'
To let reality become an intrusion,
'Cause in dreamy-dream land, I was cruisin'.
But the buzz kept buzzin', my head kept fuzzin',
Gave the radio a throw, and heard an explosion.
(Homer: D'oh!)
Opened up my eyes, and to my surprise,
There stood Homer, and his temperature rise."

The song received a positive response from critics. Sommer Swindell of the Observer-Reporter commented that "after listening to [The Simpsons Sing the Blues] once, no one will forget 'Deep, Deep Trouble' [...] It would be hard not to crack a smile while listening closely to the lyrics, as they are very creative and humorous." Thor Christensen of The Milwaukee Journal wrote that Bart "gets in a few good yuks" in the song, and Walt Belcher of The Tampa Tribune reported that Bart "raps out an amusing story about his misadventures while mowing the lawn". The Orange County Register's Cary Darling noted that "Bart turning his life into a hip-hop autobiography on 'Deep, Deep Trouble' is an absolute joy." Cartwright's rapping was praised by Tom Hopkins of the Dayton Daily News.