Year: 1997

LL is yet another rapper who seems less than discriminate about which companies he's aligned himself with over the years: Sears, Old Spice, Coke, Dr. Pepper, Direct TV. But nothing will ever top his legendary Gap commercial. Undoubtedly the hardest commercial The Gap has ever produced, it finds LL rocking a capella and sounding like his old self. But here's the real subversion: While spitting this impassioned ode to The Gap, he rocked a baseball cap branded by the logo of rising would-be rival brand Fubu, and worked its name into his rhyme. Apparently, not being the type of company that would keep their eyes on the urban fashion market, The Gap left the hat in the ad unedited. LL cashed his Gap check and left a small, but significant mark on the face of corporate fashion.