Back in the day, everyone probably said Scott Stokely should have been the best.
Came here for this. I haven't seen Simon in person yet, but I did see Stokely on a few occasions and they both kind of remind me of each other in the way they behave on the course (also like Mark Grace, for any of you who are both old enough and grew up in a Chicago Cubs household like I did). Fun to be around, joking with the fans, etc.
One time during a DGLO final 9, they played a safari hole from (IIRC) Hudson Mills original #5's tee back to #3's basket. His upshot struck the roof of the temporary tent put up nearby. When Mark Ellis was asking for scores, Stokely said "Tent!" instead of his score for the hole, causing the Lizard Lawyer to give a serious, scolding look for a brief second.
On #18, he threw a surprise huge sky anny instead of the usual hyzer route, turned to the gallery and said something along the lines of, "Fooled you!" with a huge smile.
Also, a friend of mine was following Stokely's card prior to one of these final 9's and recounted this story for me. The tournament director had pulled up in his golf cart at the Monster Hole (which is over 1,000' long) and Stokely asked him, jokingly, if he could borrow it after his huge drive. The director denied this request. A moment later when the director was away from the cart, Scott jumped in and zoomed off! I'm told the director didn't say a word when he got to the cart and drove away pissed off. Everybody else was laughing, if I remember what my friend said correctly.
I also remember Ron Russell jumping onto the back of one of these golf carts at DGLO, travelling between holes holding on and standing real tall going through the crowd with a huge grin and waving to people. I think he may have even said, "Beep! Beep!"
You know who else in modern times is a cut-up like this? Brian Earhart. He was on the feature card at the CCR open where I got to watch him, McBeth, Gurthie and Frescura and he was cracking jokes all over the place and keeping it loose. A ton of fun all round long. I specifically remember him singing Achy-Breaky Heart in comedic fashion while they waited on a back-up. Another time while they were waiting on a tee, Earhart whipped his towel on Frescura's leg to shoe-off some mosquitoes (that were EVERYWHERE on this course). "I'm sorry, did that **** with you?" Frescura joked back that it might be effecting his concentration, so Brian did it like three or four more times for good measure.