I have two to start with I DARE you to top:
-Sports: Bill Buckner. One strike away from winning it all, and "a little grounder up along first- BEHIND THE BAG! IT GEETS THROUGH BUCKNER! HERE COMES KNIGHT, AND THE METS WIN IT!!!"
(Although, as I'm a Mets fan- LUCKIEST ever for us!) ;)
-Music:
Is this even a question?
Pete Best... when you get kicked out of the BEATLES just before it all starts, AND they're rich as god, immortal, defining and transcending music and a generation and... well, they become the Beatles, AND you're replacement (Ringo!) is beloved...
Poor guy... though, again, I like the winner, Ringo's my favorite, so... ;)