Wait - there's more...

So far:

Doodi - 1
JollyRoger - 1 (actually 2, but I'm counting pictures - he got the hard one)

The last picture was Tiger and his friend Mark O'Meara before the Pebble Beach Pro-Am circa 1995.  Here's an easy one for anyone:


I guess a hint would be he's known as a choker - though he's a great golfer.