Lots of the anecdotes on this thread are really just old golf jokes regurgitated in one fashion or another. Here is the cleverest actual line I ever heard from a caddie. Playing Troon (the original, not AZ) Hit it to 15 feet on #1,leave the birdie putt 2-3 feet short. Hit it closer on #2, maybe 8-10 feet, once again hit the putt a foot or two short.
At this point the caddie might have dusted off a tired old saw like, "Never up, never in," or--"99% of putts that don't reach the hole don't go in," something we've all heard a hundred times before.
Instead, he gives me an admonishing look, and says, "you know, Joel, I can read 'em coming back too!