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1. Super Smash Bros. Brawl - I've played it many times, but I rarely play it for more than an hour at a time.

2. Warcraft III - Started playing it when it first came out. (yes, at six years old) Still playing it on a regular basis.

3. Kirby's Dream Land - Precisely sixty minutes. But I let the game sit at the title screen for a quarter-hour.

4. Neverwinter Nights - Five years. I did abandon the game for four and a half years before coming back and finishing it, but it was still the same save file and still my first playthrough. (The game I've actually spent the most time playing on my first run is probably Twilight Princess)