38 Years Ago, One Song Almost Ended Will Smith's Career Before It Even Began

While his last big hit was when he slapped Chris Rock at the Oscars, Will Smith had a run as the undisputed king of end credit raps. His song for Men in Black won a Grammy and while Wild Wild West was a box office disappointment, the soundtrack went double platinum thanks in no small part to Smith's chart-topping song. But before he was known for closing out movies with rocking tunes, Will Smith was the Fresh Prince, and he and his pal, DJ Jazzy Jeff, were almost killed by one of the most iconic horror villains of the 1980s.

In the halcyon days of 1988, DJ Jazzy Jeff & the Fresh Prince put out their second album, He's the DJ, I'm the Rapper, which became an instant hit thanks to the all-timer "Parents Just Don't Understand." Their second hit from the album was "A Nightmare on My Street," a track (and the music video) that recounts Will Smith's own battle against a frightening fiend who is "burnt up like a weenie" and called "Fred." While the rapper is able to survive the encounter, poor Jazzy Jeff isn't as lucky. And while the song was a huge hit, landing at #15 on the Billboard Hot 100, it almost ended their careers.

A Nightmare On My Street Was Made For A Freddy Krueger Movie

"A Nightmare on My Street" was initially written and recorded with the hope that it would be included in A Nightmare on Elm Street 4: The Dream Master. The song samples the motif Charles Bernstien created for the Elm Street movies and makes multiple references to them as well, quoting Freddy's Revenge with the line "You've got the body, I've got the brains" and a callback to Johnny Depp's death in the first film with "I'm your DJ Now, Princey!" With the wit and solid beats that DJ Jazzy Jeff & the Fresh Prince were known for, it was clear that the song would be a big hit with fans of both the musicians and the movies.

But, for reasons that remain a mystery to this day, New Line execs chose to reject DJ Jazzy Jeff & the Fresh Prince's track and go with the Fat Boys' “Are You Ready for Freddy." In that song, which weirdly sets up Fat Boys member Prince Markie Dee as Freddy Krueger's nephew in a rather long intro, Robert Englund raps as Freddy and appears in the video as the famous killer. The Fat Boys rap about Freddy and his antics over a superb bass line, some classic beatboxing, and samples from the movies. The song is good, but, oddly, wasn't included on the movie's official soundtrack release. It was on the Fat Boys' album Coming Back Hard Again, but their Nightmare tune never had the same impact as the one created by Fresh Prince and Jazzy Jeff.

New Line Sued DJ Jazzy Jeff & The Fresh Prince

Even after New Line Cinema decided to go with the Fat Boys, Jive Records, the home of DJ Jazzy Jeff & the Fresh Prince, continued to make a case for their artists. When that didn't work, the decision was made to include it on the duo's album He's the DJ, I'm the Rapper, and to make a music video for the song. That was when New Line's lawyers got involved.

New Line sent a cease-and-desist, claiming copyright infringement. They demanded that Jive pull the album from shelves and asked for an injunction to keep the music video from being played on MTV. Jive tried to argue for fair use, but the judge wasn't on their side, ruling that the song was too similar to New Line's IP and was trying to use the movie's promotional campaign to boost album sales. Deciding against dragging things out, Jive and its parent company, Zomba, found another way to get the song out there: they settled with New Line for an undisclosed amount.

The video for "A Nightmare on My Street" opens and closes with a legal warning making it clear that the song is not officially affiliated with the movies, nor has it been authorized by New Line Cinema. Similarly, copies of He's the DJ, I'm the Rapper had a sticker placed on the album cover stating that the song is not a part of the Nightmare on Elm Street universe. Fans didn't care. "A Nightmare on My Street" was a massive hit for the duo, helping He's the DJ, I'm the Rapper go triple platinum and ended up on their greatest hits album. These days, "A Nightmare on My Street" is a Halloween staple.