Chrono Trigger
Golden Eye
Super Mario 64
Eternal Darkness (it has 3 different "stories" and I played it 10 times easily)
F-Zero GX (awesomest racing game ever)
Perfect Dark
Metroid Prime (yes, I finished it more times than I can actually remember)
Ocarina of Time
Majora's Mask
Wind Waker
Metal Gear Solid (PS1 in 2 different languages with at least 10 playthroughs each and Twin Snakes with 10 pt's at least)
Devil May Cry
Onimusha 2
Doom 1 & 2 (too many playthroughs on too many different platforms to count and that game still doesn't bore me)
Oblivion (too many playthroughs to count through so many years in 2 different platforms, bought 3 times)
Fallout 3
Fallout New Vegas
Skyrim... pretty soon.
and some other I can't think of right now.
Golden Eye
Super Mario 64
Eternal Darkness (it has 3 different "stories" and I played it 10 times easily)
F-Zero GX (awesomest racing game ever)
Perfect Dark
Metroid Prime (yes, I finished it more times than I can actually remember)
Ocarina of Time
Majora's Mask
Wind Waker
Metal Gear Solid (PS1 in 2 different languages with at least 10 playthroughs each and Twin Snakes with 10 pt's at least)
Devil May Cry
Onimusha 2
Doom 1 & 2 (too many playthroughs on too many different platforms to count and that game still doesn't bore me)
Oblivion (too many playthroughs to count through so many years in 2 different platforms, bought 3 times)
Fallout 3
Fallout New Vegas
Skyrim... pretty soon.
and some other I can't think of right now.