This post is part of our Money Face-Offs feature. Let us know who you think comes out ahead in this head-to-head match-up, and check out our other Money Face-Off posts.
It's small wonder hip-hop stars and brand empire builders Diddy and Jay-Z are known as much for their rap sheets as their balance sheets; after all, they have more AKA's than most mafiosos.
P. Diddy is only "P." in New Zealand and the U.K., and I'll always know him as "Puffy" (and "Puff Daddy," "Sean Combs," and "Sean John"). He's gone through more name changes than Prince and all those formerly-known-as such.
Jay-Z, whose given name was also "Shawn" (though spelled differently from Diddy/Daddy/Puffy's "Sean"), also goes by "Jiggy," "Jazzy," and "Jay Hova." While it seems obvious that Jay-Z would win in a battle of the boys from the block (after all, he's dating Beyonce), and he is, after all, officially richer, still there is controversy. Whose business empire is more diverse and eclectic? Whose criminal record is more sordid? Whose clothing line is more inappropriate for the toddlers they market toward?
Putting criminal records aside for the time being (and for the record, I think Jay-Z, with a stabbing incident on his rap sheet, beats Diddy, whose gun controversy ended with an acquittal and -- most importantly -- zero bullets actually connecting with human flesh), let's compare the rappers' empires:



