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Money Face-Off: P. Diddy vs. Jay-Z

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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:

Cash money: According to Forbes, Jay-Z wins the battle in both 2006 pay ($34 million for Jay-Z, $28 million for Diddy) and net worth ($547 million vs. $346 million according to Panache).

Clothes make the men: While Diddy's clothing line, Sean John, is more ubiquitous in my house (my five-year-old actually owns two "pieces" of the line), Jay-Z has more financial gain; he sold rights to his Rocawear line for $204 million. Diddy does get props, though, for working to combat unfair working conditions in Honduras after a Kathy Lee-style controversy.

Food and drink: Jay-Z owns the 40/40 Club with outlets in New York and Atlantic City; Diddy's restaurants are called "Justin's" and have outlets in New York and Atlanta. Jay-Z seems to have the edge here, with plans to expand to Las Vegas, LA, and Singapore.

Music labels: Diddy co-founded Bad Boy Records, whose famous acts included Biggie, Ma$e, and Danity Kane, and is now owned by Warner Music Group. Jay-Z co-founded Roc-A-Fella Records, whose artists now include Rell and Ol' Dirty Bastard, and is owned by Universal Music Group.

Although Jay-Z has certainly been the most financially successful until now, it seems obvious that the frequent name changes, explosive personalities and general difficulty getting along with others will always hamper both stars' ability to effectively cash in on their stardom. Diddy's venture with MTV's Making the Band, and Jay-Z's rumored collaboration with girlfriend Beyonce, both seem to hold the greatest long-term potential for the stars; it's anyone's guess who will overcome his temper and questionable company in order to become more bankable down the road.

Vote in our poll for Sean "Diddy" Combs or Shawn "Jay-Z" Carter, and let us know in the comments why your choice has the financial edge in this match-up. Also be sure to check out our other Money Face-Offs.

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Last updated: July 09, 2009: 04:12 PM

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