Echoing the heroes of might and magic 3 recommendations. However, don't get the HD version on steam, get the original game from gog. The HD version doesn't have the expansions.
My friends and I have spent hundreds of hours playing heroes 3 hotseat.
Also, Civ V hotseat.
There is also ways to make left 4 dead 2 split screen on PC if you want to try that: http://forums.steampowered.com/forums/showthread.php?t=1029890
If you like arcade games you can always get MAME and "find" some roms like money puzzle exchanger, windjammers, contra, smash TV, sunset riders, etc.
It's the time of year where the Bacon Review does his top 31 albums of the year. There's always a few interesting things there: http://www.baconreview.com/
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