Well, it helps to take away from the pain of death to laugh at it (unless you're seperate from your funny bone by the windshield of your car having disembowled you...in which case it might be hard to chuckle). So I'll (reluctantly) get in on this:
Britney - Granted, she is an untalented attention-whore whose quest for stardom has forced "the Sinead look" back into the zeitgeist. But she does have two kids who will grow up not knowing their mother apart from tabloid reports, and that's just wrong. I'm not even giving her until summer until she has one too many Red Bulls. :(
Lindsay Lohan - Her career is pretty much in the tank, unless she can get in on the lucrative porn industry she'll be living off residuals or whatever's left of them whenever her parents get done living off her fame. Another case of parents living through their kids. 
Jimmy Carter - the nefarious plan of the Bush administration to kill off every other living ex-President is in high gear (they got Ronnie in '04, and Gerald a while back). I expect a wall to come crashing down on Jimmy while he's trying to house yet another poor family screwed by the current administration (Bill Clinton, in the White House kitchen, with the steak knife...no, wait, Hillary will be behind that one)
George Steinbrenner - the Devil has to call him on that unpaid bill, right?
One of the members of Monty Python - They're getting on, and it's been almost twenty years since Graham passed. Which I hate to say, but death is inevitable. My bet is on Palin, for some reason.
Bill O'Reilly - More wishful thinking than anything else 