I'm ashamed to say this but I watched every episode of 'Starsky and Hutch' as a kid. I loved that show but now I think it's stupid - they'd have a car chase for no reason then Paul Michael Glaser would shoot the car and it would blow up.
I think being a wealthy member of the establishment is the antithesis of cool. Being a countercultural revolutionary is cool. So to the extent that you've made a billion dollars you've probably become uncool.