Date: Spring 1997

The Moment: In the Spring of '97, a commercial starts to air for the Gap, featuring a new kind of spokesperson for the mall-shopping standard of America: LL Cool J. In the spot, LL sports the Gap neck-to-toe. On his head, however, was a hat by a then little-known streetwear brand called FUBU, which stood for "For Us, By Us," given a shout by LL in the lyrics of his rap during the commercial, with those exact words.

The Impact: Executives for The Gap were supposedly furious, once they actually realized what had happened. And here's what happened: FUBU's founder, Daymond John—an old friend of LL's from Hollis, Queens—kept pestering LL Cool J to wear his new clothing line, until LL actually a shoot for his big Gap commerical. Orders for the clothing line exploded, and FUBU became the original monolithic rapper-endorsed streetwear brand, with revenues totaling somewhere around the $300 million mark in 1998.

The Upshot: FUBU went on to inspire Sean Jean, Roc-a-Wear, et al. By the early Aughts, however, the clothing line had fallen out of style, and LL ended up suing FUBU for money he felt he was owed by the company.