Don't laugh - but, the original SimCity 2000. It's a classic and if you haven't played it in a long time, it'll provide you with some real entertainment; as would SimTower.
I recently finished playing through Need for Speed Undercover, and that was fun, although nothing really new in the series. (once you've finished the game you can replay whatever races you want, and a surprising amount of replayability is added by racing with a manual transmission instead of automatic; not to mention just tweaking your vehicle, getting more $ and buying new vehicles, etc; all the tier 1 vehicles, which are the top-end ones, handle differently from the others)
Most RPGs are poorly-made...Oblivion and Morrowind were great examples of a properly-done RPG. Get Knights of the Old Republic 1 & 2, unless you dislike Star Wars; they're pretty well-done RPGs.
Grand Theft Auto IV is a nice time-passer.
This isn't a game, but I highly recommend all five seasons of a show called The Wire.
Rams bet status: honored. Bradford still sucks.
RedAlice is right.
"VICTORYYYYYYY!" -Johnny Drama