Agricola/Power Grid are very deep games that require a lot of thought. Dunno how well they'd go over with his friends. Arkham Horror takes 3+ hours (right?) so that also might not be a huge hit.
Carcassone is nice and simple though. Ticket to Ride is also a good suggestion, though I'm biased against it since I find it a bit boring.
http://www.boardgamegeek.com/
That's a great website you can use to check out some of the games we've posted about.
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No amount of planning will ever replace dumb luck.