23. "Wake Up Show Freestyle" (1997)
In 1997, a then-unknown Eminem flew to Los Angeles from Detroit to participate in the battle-rap competition Rap Olympics. With the event sparsely attended, DJs Sway and King Tech, hosts of the hugely influential Wake Up Show, agreed to put the rapper and other competitors on-air to help increase their exposure. Eminem's two verses blended Big L-inspired multisyllabic mastery ("But I'm more toward droppin' an acapella/To chop a fella into mozzarella worse than a helicopter propeller") with blistering humor (The duo's favorite line: "Doctor Kevorkian has arrived/To perform an autopsy on you while you scream, "I'm still alive!")
"His verse stood out because it was hardcore, funny and skillful at the same time," Sway and King Tech tell Rolling Stone via email. "Humor at that level was really new. People were more impressed with lyrical/metaphor masters at that time. He had that and was adding a weird humor to it, so he definitely stood out. The feedback for weeks was all positive. ... We just remember driving home and saying, 'That kid had mad skills, man. It was unusual but dope."