Earlier this week, Ambrosia For Heads spoke with Chris Latimer, who is looking to bring back the iconic and socially-minded African American College Alliance clothing brand. Latimer, who is seeking to raise $100,000 to re-launch the company that helped fund the educations of countless students, mentioned a moment in time that, when it happened, was one of the most subversive moves in Hip-Hop and corporate fashion.

In 1997, The Gap hired LL Cool J as a high profile spokesman for its line of Easy Fit Jeans. At the time, LL was re-gaining his footing as one of Hip-Hop’s greatest MCs, after what many perceived as a stumble with 1995’s Mr. Smith album, and the arrival of a new generation of flame-spitters like Nas, Biggie, Wu-Tang Clan, Redman, Outkast and more. While LL would once again stake his claim as a Hip-Hop G.O.A.T. (greatest of all-time–an acronym he coined) MC, on “4,3,2,1“, where he squared off against Method Man, Redman, DMX and Canibus, simultaneously starting an epic beef with the latter, The Gap spot reinforced that Jack The Ripper was back.

Wearing the company’s jeans and a sleeveless t-shirt, LL kicked a frenzied verse in the commercial, punctuated by his hyper-animated movements and gestures. Aesthetically and lyrically, it was a great look for a company that was hitting its full stride and seeking to strengthen its reach with a younger, urban audience. However, one thing turned it into an inside joke that rocked the fashion and ad world to its core.

When he taped the commercial, LL was also wearing a baseball cap, a staple part of the MC uniform at the time. To outsiders, the stylish FB emblazoned on the hat likely was a cool logo that had little significance. To those in the know, however, and certainly the audience that Gap intended to reach with the spot, the letters stood for FUBU, a company that was on its way to being one of the hottest urban fashion lines of all-time. Even still, the hidden product placement likely would not have been that big of a deal, had LL not punctuated it in his freestyle with the line “for us, by us, on the low,” a coded reference to the acronym for which the company stood, For Us By Us. The result was an explosion inside the Hip-Hop community, and it eventually made its way back to Gap.

While speaking with Oprah Winfrey in 2013, LL said of the controversy “I was supporting this company [FUBU]. I was a partner in the company; still am. I wanted to support what we were doing. I felt like, honestly, that Gap was big enough to handle that and not be hurt by it, and it worked out for everybody, ’cause it didn’t hurt them. It made them cool.” LL goes on to compliment Gap for their response, saying “They didn’t pull it. That, I can give them credit for. They didn’t go into a crazy tailspin about it once they did find it out. So, whoever those executives are, ’cause we didn’t talk much back then, thank you for not.”

After that moment, FUBU went on to reach its peak in 1998, grossing over $350 million in worldwide sales. LL acknowledges that Gap, and that infamous spot, played it’s part. “They helped out a little fledgling company. They gave back, and we appreciate that.” Nearly 20 years later, Daymond John, one of FUBU’s founders, enjoys perhaps his highest profile yet, as one of the investors on Shark Tank.

Much has changed since 1997. In today’s social media world, a move like LL’s would have made its way back to Gap instantaneously, and he likely would have been fired and sued. Back then, however, it was The Ripper pulling the ultimate jack move.

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