Your most replayed video games?

Mass Effect series, Gothic 1 and 2, Mafia: The City of Lost Heaven, Vietcong, Return to Castle Wolfenstein, GTA Vice City, Red Alert 2

Mass Effect 2

Ratched & Clank 2 on the ol' PlayStation 2

Resident Evil 3

FF X :3

I was gonna say Final Fantasy X, since I think it's the one I've played more times from scratch, but counting new game+ it's probably Tales of Symphonia :)

Captain Tsubasa (NES)
Mafia 1

I like to replay Fallout and Fallout 2 every year.

Diablo series

Hype - The Time Quest
Tomb Raider I to Chronicles (all Core Design titles besides AoD (it doesn't suck that much as everybody says, but the horrible controls make it not replay worthy))
Nox
Deperados - Wanted Dead or Alive

Borderlands 1 & 2
Bioshock

Deus Ex: GOTY and Deus Ex: Human Revolution. 12 times GOTY and 8 times HR

Street Rod 1 and 2. :D

I've played through Deadly Premonition more times than I can count

The first three Sly Cooper games (wow, who'd have guessed?) and the PS2 Ace Combat games. I've completely lost count how many times I've replayed them all.

There are quite a few that I have replayed numerous times. But the one I've replayed the most is

Resident Evil 2

I've beaten it around 8 times I suppose.

I don't always replay videogames because I generally lose interest in things very fast so after I finish a game it takes a looong time to pick it up again, but for achievements I did play some games more than once and there are only a few I can think of right now.
CoD Modern Warfare, Gears of War 1 - 3 and Dead Space

Fallout 2. Finished the story(killed the final boss)more than 50 times.

I think I haven't played any game more than twice, but there are a few which I played twice.

(Mostly) in order of most played:

Chrono Trigger - So glad to see this on so many lists. I've long lost count, at least played it over 20 times.
Earthbound - who doesnt love this game? Played at least a dozen times.
A Link to the Past - probably 9-10 times.
Toejam & Earl - maybe a bit cheaty since its kind of an example of an early roguelite at this point.
Sonic 1/2 - more classics, obs.
Katamari Damacy/We ♥ Katamari - so zen, much rollup.
Dark Forces/Jedi Knight/Tie Fighter - the best games I had as a kid, played them over and over.
C&C: Red Alert 2 - Hitler iz.... out of ze way.
Fallout New Vegas - 7 times, I kept restarting due to modding more and more. Also I literally had every weapon and armour in the game in one storage place by the end.
Goldeneye 007/Perfect Dark - gotta unlock All Guns man.
Seiken Densetsu 3 (Secret of Mana) - I think maybe 6 times?
Myst/Riven/3/4 - I got to replay these all years later since I had forgotten most of the puzzles.

Dont really replay many games these days outside of mutltiplayers/roguelikes. Even if they are really good, we're all so spoiled for choice and have large backlogs thanks to steam. Helps explain why so many of these are games from my youth.

By far Super Mario Bros Deluxe Edition for GBC.

View attached image.

Stalker

Mafia CoLH, Diablo 2, NFS Underground 2, AoE2, Commandos.

Castlevania Symphony of the Night. I once was off from work for a week so I cleared the game 3 times, each time getting a higher percentage.
That and FF6. The greatest one EVER!