The Plan

War In The Pacific Admiral edition, Arcanum, Baldur's Gate, Falout Tactics, Commandos 1, War In The East, Revolution Under Siege, Ageod Civil War 1, close combat normandy, shogun total war 1, panzer campaigns smolensk 41, hps Jena-Auerstadt, hps campaign peninsula, master of orion 3, age of empires 2... too much to count.

Need for Speed Carbon (x2).
Pokemon Yellow (x3).
That's it. For a casual gamer, quite an accomplishment :D

GTA San Andreas, MGS3 snake eater, mass effect, borderlands, DARK SOULS and alot more

The Longest Journey ( 7 or 9 times)
Dreamfall: The Longest Journey ( 4 times)
Syberia 2 (3 times)
Diablo 2 LOD (In multi... i don't know..)
Fallout 2 (2 times)
Arcanum : (3 times)

I don't remember other games.. :)

Minesweeper ! Finished that b^^^h so many times :))

Red Alert 2. Age of Empires games. Just Cause 2. Borderlands 1. FTL: Faster Than Light. Fable - TLC. Driver San Fran. Skyrim.

I'm also going to finish Far Cry 3 and Ref Faction Guerilla again (only played them through once each.)

Batman Arkham Asylum,
Bioshock 2,
Fallout New Vegas,
Alan Wake,
GTA IV

Borderlands
Dead Island
Mafia
Mafia II
Portal
Portal 2
The Walking Dead
BioShock
Limbo
Street Rod 1 & 2
Machinarium
. . .

Fallout 3 - Skyrim - Darksouls - Mass Effect 2

HL3

Portal.

Overlord
Overlord 2
Dragon Age: Origins
Dragon Age 2
Evil Genius
The Witcher
Psychonauts
GTA IV
Skyrim

Alpha Protocol.

I see so many ppl say they beat at least one of the GTA games :D

All the games in the Sly Cooper series

I have done this with like hundreds of games throughout my lifetime. But just for more recent games:
Far Cry 3
Saints Row 3
Skyrim
Borderlands 2

And the one game that I've played through more times than any other would probably be either Mega Man 2 or Super Castlevania IV

STALKER.

What games did you finish multiple times?

My wife

Serious Sam Classic (2001).
Finished it like 50 times, I never get bored of it.

I've finished Legend of Zelda: Ocarina of time, N64 at 100% so much times....best game ever :)

A lot of games. Deus Ex Human Revolution is the most latest one.

Deus Ex, Deus Ex Human Revolution, Return to Castle Wolfenstein, Metro last Light, Bioshock, Bioshock Infinite, F.E.A.R., F.E.A.R 3, Half Life 2, Painkiller, Bulletstorm, Red Alert 2, Red Alert 2 Yuri's Revenge, Max Payne 2, Assassin's Creed 1 and 2, The Witcher, Neverwinter Nights, The Suffering, The Suffering: Ties That Bind, S.T.A.L.K.E.R. - Shadow of Chernobyl, Lord of the Rings Return of the King, Far Cry, Jedi Knight: Jedi Academy, Dead Space...quite a lot, actually, almost all the games that I really liked over the years. Oh, also the three GOOD Prince of Persia games(the Sands of Time trilogy, not those two shit-fests that came after which I didn't even finish once).