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.

Critical reception of the song was positive, with its humorous lyrics and Cartwright's performance being singled out for praise.

[15] 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.

The music video for the single premiered on the Fox network in the United States on March 7, 1991, together with the Simpsons episode "Bart's Dog Gets an "F"" of the series' second season.

The video for "Deep, Deep Trouble", starting with Bart being shoved into what appears to be a jail cell, illustrates in flashback the things Bart raps about in the song, showing how he is forced by Homer to mow the lawn after throwing a buzzing alarm clock at his father in his sleep.

They make a mess in the house and when Homer and Marge return home, Bart realizes he is in deep trouble.

[21] Gregg Vanzo directed the video, which, according to him, features quicker character poses than in episodes of the show to allow the animation to match the hip-hop beat.

[21] The music video was later included on the 2002 DVD boxset The Simpsons: The Complete Second Season, with audio commentary from its producers.