Date: 2005

This was one of the more memorable competitive moments between the two superstars. Kanye had released "Diamonds From Sierra Leone" as a statement record, and then recruited Jay for a remix that would appear on his sophomore album, Late Registration. Preparing for the lyrical showdown, Kanye removed both his verses from the original song and came with fresh, all-new, socially-conscious material about the illicit trade of "blood diamonds"—putting himself in and his own material desires, and really, all of America, in the crosshairs. "Over here it's a drug trade we die from drugs/Over there they die from what we buy from drugs," Kanye says.

But Jay steals the show. The quotables are myriad, and forever memorable: "How could you falter when you're the Rock of Gibraltar?" Jay said. And, "I'm not a businessan/I'm a business, man..." (He sure handled his business. Damn!)

Kanye seldom concedes defeat. In regards to the "Diamonds" remix, though, he gave it up two years later on "Big Brother," saying, "I swore I spazzed/Then my big brother came through and kicked my ass."