http://store.steampowered.com/app/99200/
If you're not familiar with the You Don't Know Jack series, it's a crazy trivia game series from the 1990s. It's old enough that I actually own the first two installments for Mac, and they require OS 7.5 or later. The Jellyvision people have brough the series back on all current-generation consoles and PC (link to Steam above) and I wholeheartedly suggest you go out and buy it. Especially if you like trivia games and you like smarmy game show hosts. It's just seriously off-the-wall, and there are enough questions (70 episodes, 21 questions per episode) that it shouldn't get repetitive any time soon, and for $20 I can think of lots of games I bought at or above that price that won't bring me nearly as much enjoyment.