Deus Ex & DX2: Invisible War. Only problem is the first game was much better than the second, so playing them backwards would almost be a better experience... but both are great titles and sell for bargain-bin pricing. (I think you can get them both on steam for like, $25 total. Not bad at all, especially considering you wont be pestered to insert the CD!)
Monkey Island 1-4. (The Secret of Monkey Island, The Secret of Monkey Island 2: LeChuck's Revenge, Curse of Monkey Island, and finally Escape From Monkey Island) Classic point-and-click adventure games. Very casual and thought oriented. The first two are very old now, early 90s, and require you to download SCUMMVM to play them. (Or have an old computer running an actually copy of DOS.) The two newer games are voice acted, which will spoil you if you play them first. Some of the funniest inside jokes in the video game industry come from Monkey Island, so you should definately look into finding a copy; tends to be most stores no longer carry any of the titles, but you can probably get them for cheap on ebay - and i think gametap.com may be offering them as well.
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