I caddied for 10 years as a kid so this may take some time for me to come up with my best story, but here's a few:
1) I often caddied with a good friend for a regular big money game and we always had side action, so his team is one down going into 17, a par three, but they have the tee. Both his players miss the green, my first player gets up and in the middle of his back swing by buddy pours a cup of cold water down my back (we're both tee side). I didn't even flinch. Now that's a good caddie
2) So we're all in the caddie yard and there's some talk about an old timer caddie named "Leo." He'd been a real quirky guy with at least two crooked eyes who was always carrying some kind of smoked meat around in his back pocket and someone cries, "hey, isin't Leo dead!" Leo, wairing a Donald Duck hat and sitting two seats away from the questioner doesn't even blink and the entire yard hits the ground laughing.
3) White Rock, a middle-aged drug addicted caddie who was nicknamed after his habbit of choice, used to routinely get benched in the caddie yard for showing up late, drunk, drugged, not showing up, etc., would do a dance of protest that he self proclaimed "The White Rock Shuffle" and while shuffling around the caddie yard he would sing, with wiggling brown stubs for bottom teeth, the following tribute to the head pro at the time who would bench him:
"I fought Malloy . . . and Malloy won,
I fought Malloy . . . and Malloy won,
Rackin' traps in the hot sun . . .
I fought Malloy and Malloy won . . .
I fought Malloy and Malloy won . . ."