Dolla Dolla Bill Y’all: No. 1

'All About the Benjamins'
--Puff Daddy (aka Diddy) (1998)

Quotable: "Now... what y'all wanna do?/Wanna be ballers?/Shot-callers?/ Brawlers/Who be dippin' in the Benz wit the spoilers"

In 1998, the man now known as Diddy was still working his way to mogul status, but he wasn't far from it. Now,he's about more than the benjamins. The entrepreneur has his hand in everything from fashion to film.