What games did you finish multiple times?

GTA San Andreas. almost 10 times B)

Fallout 1 and Fallout 2

PC

• Age of Mythology - 5 times
• Harry Potter and The Chamber of Secrets - 4 times
• Harry Potter and The Sorcerer's Stone - 3 times
• Portal 2 - 2 times
• The Lord of The Rings: War of The Ring - 2 times
• Hunted: The Demon's Forge - 2 times

PlayStation 2

• Gauntlet: Seven Sorrows - 3 times
• Devil May Cry 3 - 2 times

PlayStation Portable

• Crisis Core: Final Fantasy VII - 2 times
• The 3rd Birthday - 2 times

Game Boy (Advance)

• Pokemon Red/Blue - 4 times
• Fire Emblem - The Sacred Stones - 3 times
• Fire Emblem - 2 times
• Lady Sia - 2 times

Rune Factory 3, Katawa Shoujo.

NES:
Super Mario Bros 1, 2 and 3
Super C
Megaman 3

PC:
Prince of Persia (1989)
Another World (1991)
Flashback (1992)
GTA: San Andreas

Assassins Creed franchise (Apart from 1 and IV)
Civilization V(does it count?)
Star Wars Forced Unleashed 2
Lego Star Wars Trilogy and EP IV-VI (not the clone wars one)
BurnOut Paradise
Most of the Need For Speeds before Undercover
Borderlands 2
Saints Row 3rd
Flatout (All but Flatout 3)
Star Wars BattleFront 2

I've completed the first Darksiders multiple times on different systems. Still need to finish it on Steam now. I've also beat Eternal Darkness from the Gamecube many times. Then of course many classics like zelda, mario and many other games from my childhood.

very few... let's see
Rez
Half-Life 2
Portal 1 + 2
Fallout: New Vegas
most of the old Sonic games.. especially Sonic 3 & Knuckles
i think that might be it, if you don't count multiplayer (I've probably put 1000 or so hours into street fighter)

Super Robot Wars Original Generation 1 & 2

RE2, i can still play the game in a single sitting without a save. It's about the only game I can even come close to doing that to still.

GTA San Andreas
GTA IV
Gothic 2
Gothic 3
Risen
Darksiders
Dishonored
Fable
Age of Mythology
TES Oblivion
Skyrim
lot more.

I'm sure I'm forgetting a few, but here's everything I can remember beating start to finish more than one time.

9 Hours, 9 Persons, 9 Doors
Blast Corps (Multiple runs with all platinums)
Bomberman 64
Chrono Trigger
Deja Vu
Dragon Quest 4
EarthBound
Final Fantasy: 1 - 6
Final Fantasy Legend III (This isn't in with the FF games because it's really the SaGa series)
Grand Theft Auto: San Andreas
Illusion of Gaia
Legend of Zelda: Link to the Past, Link's Awakening, Ocarina of Time, and Majora's Mask
Lufia 2
Maniac Mansion
Mega Man: 1 - 8
Portal
Shadowgate
Shin Megami Tensei: Strange Journey
Solstice: The Quest for the Staff of Demnos
Sonic Generations
Super Mario: Bros 1-3, World, and RPG
Vampire the Masquerade: Bloodlines
VVVVVV

Like I said, there are probably a few more. And I didn't count games like FTL and Rogue Legacy where you're meant to play through a ton of times but never actually reset your save data.

1st one that popped into my head was

Humpty Dumpty in the Garden