I can mostly think of athletes: Michael Jordan Tiger Woods Magic Johnson Jason Biggs Jim Grey Pete Sampras
Michael Jordan and Tiger Woods radiate echelon-1 swag. That is personality, they let their walking do the talking. Magic Johnson reminds me off the Pillsbury doughboy, but that's still a personality. I'd go with Tracy McGrady.
Seems like most people on posting sport stars. But I'll say. Paris Hilton Michelle Wie Tiger Woods Andre Johnson ( I love him, but you gotta admit he is boring)
What's the point of this thread again? Oh yea, so we feel better about our great personalities but mediocre careers.