My best upgrade ever was a huge suite upgrade at the Ritz Carlton Los Angeles. When I went to the room there were all these people in the hallway. It turned out Lady Gaga was in the suite next door for her movie premiere. I ordered room service and when the server came he told me he thought I was someone important since Lady Gaga was next door.
I did get upgraded one to the Club Level at the Ritz Carlton in Laguna Niguel- I think it was an oversold situation and once had one of the worst rooms possible in the corner facing a wall.