I don't know much about Gilligan's, which was beside the old Sears building and behind the old Punch Line on an odd little isolated segment of Senate Street. It keeps coming up in comments as a place fondly remembered though. I know they had sort of a big "sandbox" in front of the rather decrepit-looking building with a volleyball net set up, and "incentivies" to get folks there. Commenter Dennis notes:
Gilligan’s, A.K.A. Ribby’s, was a brilliant idea by Tim Peterson, but he could not get people there. He asked me once why the great BBQ joints never seem to sell beer (he did) and I’m still trying to figure that out. You’d think that alone would draw a crowd. Not to mention girls in bikinis playing volleyball on the sand, which he arranged to have happen from time to time.
When I took these pictures, I noticed a guy working on the roof (and who was giving me the evil-eye, so I didn't take many shots or get any closer), and commenter John says
Is my old hangout about to reopen?
Perhaps we'll see soon.
UPDATE 24 July 2010 -- It's now open as The Cock Lounge: