Moe Howard or Larry Fine would be my first choices. Maybe Moe can forecaddie.
2nd choice would be Eddie Izzard, in drag, playing with Mucci at Garden City.
With Barny and Anthony Gray in the group.
I'm an enormous proponent of the idea men and women should have separate clubs, but it would be interesting to find out whether Eddie Izzard (who claims to be "An Executive Transvestite") would be in violation of the rules.
Since Anthony Gray has slept with more women than Wilt the Stilt, I wonder if he'd try to notch my caddy in his bedpost.
My production crew would film the match in the same style as "Shell's Wonderful World of Golf" - with Uncle Bob Huntley commentating. I see a Golden Globe for Best Comedy.