Jay-Z and Kanye aren't the sort of guys that back down from a challenge. Which is why we didn't ask for their opinion when facing them off.
Jay-Z: His platinum-selling 1996 debut "Reasonable Doubt" quickly established him as an artist to watch and you'd struggle to find a hip-hop fan who doesn't consider "The Blueprint" a classic. Several recent records, however, (including "Kingdom Come" and "The Blueprint 3") generated far less universal acclaim.
Kanye (winner): Yes, he's made fewer than half the full-length records that Jay has. Yet Kanye's only critical flop ("808s & Heartbreak") is generally viewed as a bold, respectable diversion even by detractors; from 2004 debut "The College Dropout" through last year's extraordinary "My Beautiful Dark Twisted Fantasy," many argue Kanye's made one great album after another.
Jay-Z (winner): His uber successful Rocawear line covers seemingly every category for which you, your significant other or your little sister needs to shop—and it may or may not help you achieve the quintessential Jay-Z swagger whenever you Rocawear-it.
Kanye: Sure, the Olsen twins turned up for the debut of his women's clothing line (DW, which Kanye obviously didn't realize could stand for "Don't Wear"), but reviews were scathing. He also, of course, has designed shoes for Louis Vuitton and Nike.
Jay-Z (winner): He topped Forbes' 2011 list of Hip-Hop Cash Kings with earnings of $37 million and a net worth of $450 million.
Kanye: West came in No. 3 on the same Forbes list with earnings of $16 million in 2011.
Jay-Z (winner): He has, as he's said, "the hottest chick in the game wearing my chain." Jay-Z was already a giant rap star, but marrying Beyonce helped him become a special brand of hip-hop royalty.
Kanye: His most publicized relationship (outside of his engagement to designer Alexis Phifer) was with Amber Rose, currently dating/engaged/married to/whatever with Wiz Khalifa.
Jay-Z. Kanye's one of the planet's biggest rappers—and he'll be the first to say so—but he needs a few more years of uncomplicated success before he can truly stand beside his hip-hop teammate.