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There are some strategy games that are designed to play through many times.  The biggest one for me is probably Civilization Revolution which I think I've played through around 50-100 times.  Also, Civ 1, Civ 2 and Master of Magic have had more playthroughs than I can count.  For more story/campaign oriented PC games, I've played through both Freedom Force and Heroes of Might and Magic 2 at least 5 times each (maybe more).

Then there are the NES games.  I've played through Super Mario Bros 1 and 3 and The Legend of Zelda a ton.  I've played these games so much (and so long ago) I couldn't tell you if I beat them closer to 4 times or 40 times.  Most likely somewhere near the middle of that, lol.  I've had a several playthroughs of NES Metroid too.  None of those games takes a long time to beat though.  

Golden Axe and D&D: Tower of Doom also fall into the 4-40 times playthrough category.  Some of those times were multiplayer though and some were by myself.

Final Fantasy games:  FF1, FF7 and FF Tactics I've beaten like 5-10 times each.  FF9 and FF10 are more like 4-6 times each.

Katamari Damacy is a game I've beaten around 8-12 times.

Oh yeah, and Adventure on the Atari 2600 I've beaten like 20-50 times, but again those playthroughs do not take long.