42. The Madd Rapper feat. Eminem, "Stir Crazy" (1999)
When Deric "D-Dot" Angelettie of the Hitmen – the production squad responsible for Bad Boy Records' array of Nineties smashes – assembled his debut "Madd Rapper" album, Eminem was one of the few currently popular rappers with whom he hadn't worked. "I called him up and said I was a fan of his, and he said he was a fan of mine, too," D-Dot told MTV News in 1999. Collaborating with a then-unknown Kanye West as co-producer, the result is a loony game of wits between an upstart Slim Shady (fresh off his "My Name Is" success) and D-Dot's churlish Madd Rapper persona. "Psyche, no bread/Fucked up in the head/Shot my girl and my sister 'cause I caught them in bed," rhymes the Madd Rapper in a punchy Nuyorican flow reminiscent of the Beatnuts. But Eminem is clearly the superior stylist, dropping oddball stanzas like "I'm crazy with this razor/With this razor I'm crazy/With this crazor I'm razy/Razor cray, I'm crazy!" The Madd Rapper eventually concedes defeat: "Fuck that, Slim, keep that for yourself/You a crazy white dude and you need some help."