Songfacts®:

• In 1990, after the second season of The Simpsons was in the can, the team put together an album called The Simpsons Sing The Blues, expanding the franchise to music. The first single was "Do The Bartman," where Bart introduces his own dance. The next single was "Deep, Deep Trouble," where Bart recounts one of his more adventurous days. He sleeps in but is roused by Homer, who orders him to mow the lawn. He ends up hitting a sprinkler and then throwing a party, landing him in deep, deep trouble.
• Simpsons creator Matt Groening wrote this song with Jeff Townes, better known as DJ Jazzy Jeff. With a jaunty, easygoing beat and lyrics that tell a kid vs. parents story, it's a close cousin to Jeff's work with the Fresh Prince (Will Smith), especially their 1988 song "Parents Just Don't Understand." Will Smith absorbed all the spotlight, but Jazzy Jeff was a renown DJ and producer with a talent for making beats that won't leave your head. He also produced "Deep, Deep Trouble" and added the scratches.
• The voices on the song are the ones from the show, including Nancy Cartwright as Bart and Dan Castellaneta as Homer. The animators on the show made a music video for the song that was included on the second season DVD.
• Want to connect Eric Clapton to The Simpsons? We can do it through this song. One of the backup singers is Marcy Levy, who sang with Clapton for many years and co-wrote his song "Lay Down Sally."