A game you've played through the most times.

I'd say Kingdom Hearts and Deus Ex Human Revolution are the games I played through the most.

Many. Kingdom Hearts 1&2, Medal of Honor Vanguard, Golden Sun, Pokemon Diamond, Yugioh: Dark Dueling Stories, Sonic Heroes, Grand Theft Auto IV, Rogue Galaxy, and many others that I can not remember.

-Custom Robo's initial story mode. I've beaten it at least twice a year until 2 years ago.
-Mega Man 2 & 5. I'd beat them like once a month when I get bored of my other games.
-Freedom Fighters. Around 11 times.
-Zelda: Wind Waker. I just really liked the counter system.
-Starfox Adventures. Because apparently, I'm the only one that liked this game.
-Metal Gear Solid: The Twin Snakes. It literally takes me two hours to beat this game if I skip the cutscenes.
-Phoenix Wright 1. I always forget how to beat the game, so it helps keep me sharp about searching for evidence.
-Smash Bros. Brawl's story mode. I don't know why either.
-No More Heroes 1.

And Skies of Arcadia. I love this game.

I've only included games that I've beaten more than ten times after starting either a new game or a new game+.

Super Metroid, Link to the Past, Megaman and the X's, and the side scrolling Sonic's come to mind. Almost a yearly replay with some of these!

I would say the original Paper Mario. I've played through it at least 3 - 4 times. Although Thousand Year Door is the superior game in most respects I still enjoy the original the most mainly due to nostalgia. I grew up watching my brother play it and I have fond memories of it. I remember one time actually bringing it to my parent's sandwich shop and playing it on the tv there.

I've never gotten all the star pieces though, since I'm not that much of a stickler for 100% completion.

Also Earthbound. I don't have much nostalgia since I played it on an emulator so I just like it as a game in general.

Baldur's Gate 2 and ToB. I have Irenicus' entire dialogue memorized. Am I... old?

Any of the Saints Row games, Dragon Age II, Metal Gear Solid 3, Dynasty Warriors 4, something else I'm probably forgetting.

FFX international. That game really pushed me to dozens of hours grinding just to take on the dark aeons, the arena monsters and Penance. Also do some personal challenges. With FFX-HD out for the PS3, I'm back to grinding, rage quitting, and spending my free time on this game.

In terms of recent games, I'm pretty sure it's either Mass Effect 1 or 2. I've had multiple runs on both games for achievement hunting, Paragon/Renegade runs, and playing with each class at least once.

I'm currently on my 16th playthrough of Dark Souls 2 & completed Dark Souls 1 about 30 times across multiple characters...

I really like Dark Souls apparently
._.

Probably the entire Half-Life series. Ever since Half-Life 2 came, i have played all the games in one stroke when ever a new game came up, and after Half-Life 2: Episode 2 and Blackmesa, i have played them all like couple of times every year or so.

Half-Life 3 WHERE ARE YOUUUUUUUUUU!?

I've played through Final Fantasy 8 and 9 around 5-10 times each... and also many of the tales series' games; Symphonia and Vesperia being the most at around 5-10 times each as well. I've also played through the Disgaea series multiple times with the original Disgaea being the most played.

Pretty much older RPG games from the PS2 era and before are the ones I replay a bunch.

I will also agree w/ Disgaea 1 since I was trying to get all the endings.
Pokemon Leaf Green since I'm trying to clear the Pokemon League, then migrate the pokemon I used to Pokemon Diamond to win the Sinnoh League, in w/c I will migrate them to Pokemon White to clear the Unova League, in w/c I will migrate them to Pokemon Y to clear that region's league.

Countless times also for Super Robot Wars for the GBA for R, Original Generations 2, for the DS SRW of W, K and L.

Super Mario Bros 1, USA, 3 and World. Countless times for Super Mario Land 1, 2 and 3. Countless times for Kirby's Dream Land 2.

-DarkdaemonPK2