2. Eminem & Royce Da 5'9" "The 12 Minute Freestyle" (1998)
Station: WKCR (89.9FM) DJ: Stretch & Bobbito Best Punchline: "Spit spectacular, crystal meth manufacturer/Stole your momma's Acura, wrecked and it sold back to her." (Eminem)
Back when aspiring rappers actually had to prove they had bars to gain acceptance in the hip-hop community (especially if said rapper was a white boy), Bad Meets Evil approached the scene with reckless abandon. For 12 unforgettable minutes on Stretch & Bobbito's airwaves, the new kids from Detroit proved that they could compete with even the greatest and most established rappers in the game.
Complex EIC Noah Callahan-Bever was in the studio for this freestyle (read about his wild and crazy experience here) and rumor has it that both Bad and Evil had indulged in a little bit of ecstasy before jumping on the mic.
With Em playing the comedic role: “Stole your Mama's Acura/Wrecked it and sold it back to her;” Royce was far more menacing, kicking threats like: “I got cats with bats you wouldn't play hardball with.” And if you think Game's a name dropper, Slim Shady called out more celebs than you could count on four hands.
It's just a shame it took upwards of twelve years for these two to rekindle their working relationship. But it was evident early on that they were poised to do big things.