Sean "P. Diddy" Combs
Harlem-born Sean John Combs, who later dubbed himself "Puff Daddy," "P. Diddy" and finally, "Diddy," wears a lot of hats: rapper, songwriter, dancer, movie and music producer, restaurateur, clothing designer and actor. Now he wants to add another lid to his collection -- that of NFL football team owner. While Combs (who is worth an estimated $380 million) probably has the wherewithal to fund his latest bucket list, we're betting the inspiration came from much earlier experiences. He has been a Pop Warner football coach in Mount Vernon.