Producer: Mark C. Rooney, Mark Morales, Sean "Puffy" Combs, Daddy-O
Album: N/A
Label: Uptown

By the time Big passed in 1997, he was the poster boy for the hip-hop/R&B duet. Time and again, he proved the perfect recruit to eloquently thug out the softer sounds that were so popular on the radio. His verses worked like a charm—converting heads who otherwise wouldn't have been caught dead bumping slow jams. But back in '92, he was very much unproven.

Though it was only the rapper's second guest appearance, Puff believed in Big enough to add him to the remix of “Real Love,” the breakout song by Diddy's other muse, Mary J. Blige. Still rocking with the Biggie Smalls moniker (before switching to Notorious thanks to an obscure white rapper who'd already trademarked the name), the unapologetically grimy Biggie stole the show with his “Look up in the sky it's a bird it's a plane” intro. Sure Big was rough around the edges, but he didn't sound at all out of place alongside Ms. Mary. On this day a star was born.