D.J. Jazzy Jeff and The Fresh Prince (aka Will Smith) released their first single while Will was still in High School, Girl’s Ain’t Nothing But Trouble. The song sampled the theme song from I Dream of Jeannie. That choice turned out to be a little bit of trouble as well. It ended well for the duo when Jive Records signed them to their label. Their first album for Jive did not produce any standout singles, but their second album made them superstars.
The first single from He’s the DJ, I’m the Rapper was Parents Just Don’t Understand. The video for the single went into heavy rotation and the disc was awarded a gold record. Their second single was A Nightmare On My Street, which got up to #15 before it stumbled.
For years fans debated the existence of a video for Nightmare that included cameos by Richard Englund, the original Freddy from the Nightmare on Elm Street films. It has been reported that New Line Cinema sued over the video, causing it to vanish for a few decades. In 2018 a video resurfaced on YouTube. The video clearly looks like it was made in 1988. While it does not feature Robert Englund, it does include footage that might well be from some unnamed horror films…and it does mention Elm Street in the rap and refer to a monster with claws as Fred. Big warnings at the start and end of the video inform viewers that it has nothing to do with the Nightmare films, the same kind of warnings that were on the album.
A reworded version of Girls Ain’t Nothing But Trouble was released next, and a year later the group put out I Think I Can Beat Mike Tyson, but neither record got any higher than the bottom half of the Hot 100.
The duo had their biggest hit with Summertime in 1991 and followed that up with a few more singles that reached the top twenty. Will Smith went on to a solo career in television, movies, and music, but the original duo still performs in public from time to time.