Dre and Pac worked together on some of the rapper's most classic hits, including the West Coast anthem "California Love." Dre always preferred to keep a lower profile than the artists he worked with and mentored, so we like That's So Raven star Massey. True, Massey has lived a very different life than Dre, but you gotta admit the resemblance — especially those cheekbones! — is striking.
(Photos from left: Raymond Boyd/Michael Ochs Archives/Getty Images, Araya Diaz/Getty Images)