Out of the movies on the list, I would have to say that Caddyshack is my favorite.
Bill Murray is an amazing comedian. I never really appreciated him as a dramatic actor until recently. I liked Lost in Translation enough but didn't find it particularly brilliant. Broken Flowers however was one of the best films I've seen lately. Absolutely brilliant performance from Bill Murray and everyone else involved, particularly Sharon Stone (who I don't particularly like most of the time) and Jeffrey Wright (an enormously underrated actor with tremendous talent). I love everything Jim Jarmusch has done, and I was a little dissapointed when I first heard he was doing a romantic comedy type film (I was hoping for something more in the vein of Ghost Dog and Dead Man, two of my favorite films) but Broken Flowers didn't dissapoint one bit.