This is sort of the MVP Award of the October Classic. The winner needs not to actually win the Classic--though it would certainly help--he only needs to be the player who best exemplifies the "silly", when playing this silliest of contests. We didn't have this award for the first three Classics, due to two reasons; one, nobody really stood out as particularly silly, and two, I didn't have the idea yet. It was only when Eric Morin and his neon yellow afro-wig showed up at the doors of 4th October Classic, did the concept first form in my mind. At the time, I quietly made a mental note to myself that, "brown jacket or not, this man well deserves a prize for his silliness."
Why Bill Murray, and not let's say, Carrot Top, or perhaps even Larry the Cable Guy instead? Well, because Bill Murray is the rarest of creatures. When Murray speaks, you have a very difficult time discerning whether he's acting silly or being dangerously serious. In my opinion, nobody performs this balancing act better. And what better symbol for our event, than that? Oh, well, that and the fact that Bill Murray isn't too shabby a golfer either--and that Larry the Cable Guy isn't funny at all.
The award itself will be a simple one. It will be a framed image of the Bill Murray, as well as some example of media that displays his talent. It might be movie, a book, soundtrack, 
or maybe even an autographed print of the man himself (you can buy this sort of thing easily on Amazon).
The winner will be chosen by means of group vote. All assembled sportsmen and Octobermen at the end of the Brown Round will get one vote. Any potential tie-breaker will be held by chairman (me).
Is it worth anything? Not really. Will you admit to anyone you've actually won a Bill Murray Award? Probally not. But, in all honesty, will you be able to suppress a smile, any time you pass by your hall, and you see this award sitting on your bookshelf? 
Never in a thousand years.

Eric Morin

Phil Doucette

Denis Ouellette
Leigh Brooks
Pierre Gendreau

John Beaulieu

Phil Doucette
John Hebert

Johnny O

Nick Labbe

John Beaulieu

John Hebert

Pierre Gendreau