Eminem & Proof’s Legendary 1999 Freestyle Is Re-Released In Its Entirety (Video)

1999 was thee year for Eminem’s career. Three years removed from Infinite, the Detroit, Michigan MC would team with Dr. Dre and Aftermath Entertainment to unleash The Slim Shady LP in February and things have only exploded since. That year, Em’ would travel overseas, including making a stop to Tim Westwood’s London, England radio show.

Although Proof would not appear on Em’s major label debut, he was reportedly signed by Marshall Mathers that same year as the first act on Shady Records. While D12 would be Shady’s first vehicle, the bond was especially strong between the two battle-tested MCs. On the road, as customary at the time, Em used every opportunity he could to help brand the rapper he’d grown up with. Westwood would be a critical stop for both MCs.

With Tim at the controls, Eminem started things off rhyming over some Def Squad dopeness. Here, Em’ would divide his rhymes with off the top flavor, and lines like “Original bad boy on the case / Cover ya face / Came in the place / Blowed, and sprayed Puffy with mace” (Em’ would also name-drop Ma$e again) Handing the mic to Proof, the D12 front man gets busy, making it clear he too, is improvising.

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In the extended freestyle (shared in full by Westwood), Eminem raps about his Rawkus Records 12″, while Proof pokes fun at R. Kelly stealing Aaron Hall’s style and jokes about Tupac Shakur hiding in Cuba. Around 7:00 in, the pair busts some bars at Canibus’ experience. When the beat switches to Nas’ “Hate Me Now,” Eminem and Proof makes a host of Rap cracks, including at Master P, Charli Baltimore, and Ma$e.

Lovers of jokes about drugs, violence, and disease will especially love this pure Slim Shady/D12 moment. What’s more, the pair make fun of Tim Westwood’s enthusiasm too. Nobody was safe from the Dirty Dozen in ’99.

Coming up on one decade after his murder, Proof’s talent is missed just as much as his character.

Related: This 1998 Cypher By Eminem & Royce Da 5’9″ Was A Preview Of Much Greatness to Come (Mix)