Before I start, I must disclaim that I had never seen the show until Jaime posted clips at his site. So, if one wishes to dismiss my opinions as bunk, feel free...
I really do like the basic concept of Celebrity Sweepstakes. It has that simple, yet very engaging quality that everyone looks for in a good game show. Also, the gambling element might prove popular with audiences who enjoy poker shows and their ilk. So...if the show were to come back, would you see it working?
I would say it would, but I'd like to fix what I believe is the show's main problem: the celebs themselves. Like HS, they need to be funny and crack jokes, but unlike HS, they're on their own as far as real answers to the questions go. When the celebs have to worry about both aspects, the game really tends to drag in spots (not to mention poor Jim McKrell, who looks very uncomfortable in these spots trying to shut the panel up and keep the game moving).
My solution? Replace celebrities with a panel of "experts"--Ken Jennings, Kevin Olmstead, and any other folks (not necessarily game show contestants) who are known for having a head for knowledge. Yes, some of the humor might go out the window, but the game aspect would become stronger, and--after cranking up the difficulty of the questions considerably--the enjoyment of seeing so much brainpower tackling extraordinarily tough material might make up for it. (And yes, I know the name would need to be changed. Perhaps "Scholarly Sweepstakes?")
Just an idea...
--Sam