I loved this show! I came to love the titular curmudgeonly genius of Ben Stein! Jimmy Kimmel first came to my attention through this show. Lots of good stuff.
From the naughty titles to the sometimes spooky-smart guests to the final showdowns that sometimes had me gaping in surprise, I enjoyed every half hour I spent in front of this show.
Granted, it's just a trivia show not unlike Jeopardy!, a forefather of random knowledge shows. It's the set-up of Ben's (and Comedy Central's) cash being on the line, the possibility of out-remembering just that one piece of information so that you get to take that cash from Stein, that makes it irresistable. That and that Mr. Stein seemed genuinely happy for the folks able to best him at the game.
After watching this, Jeopardy! may be considered the gold standard of gameshows, but Win Ben Stein's Money is the platinum standard.
Strongly recommend this show to anyone.