NOTE: Shaun and Jason have already had their takes on this issue. You should check them out if you haven’t yet.
Shaun started a list that focuses on the replayability of games. It’s now my task to go through something similar and see what makes the cut. Sorry, awesome game that I never had the chance to finish (looking at you, Final Fantasy IX) or have only played once (looking at you, Fire Emblem Awakening) — you don’t get to be on this list.
While I’m a bit of a sucker for nostalgia, I don’t frequently have the time to go back and play things that I’ve already beaten. The new release list takes precedence sometimes. That said, there are a handful of titles that I’ve poured time into in my life for a variety of reasons. I’m going to stick with games that I’ve beaten three times or more, similar to Shaun’s list.
A “playthrough” is a little tough to quantify sometimes. How does one beat Mario Kart Double Dash? By winning any cup mode, any CC? By winning 150 cc mirror all-cup mode? What about an MMO, where the game carries on in perpetuity? I’m going to have to clarify a couple things as we go, I guess.

Super Mario 64
Times played through: 3
I’m surprised that I haven’t beaten this game more times than this, but this is all I’ve got. I played the original way back when it as first released on a rented Nintendo 64 in Colorado. I played it again when it was released on the Virtual Console, and then one more time for nostalgia’s sake. Even though the graphics don’t necessarily hold up that well, the play experience absolutely does — and that’s probably why SM64 is one of the most influential games of all-time.

Pokemon Gold/Silver
Times played through: 3
There’s some minor cheating in this one — I’m counting HeartGold on top of the original Gold. I beat the Game Boy Color game while on vacation in Buffalo when I was still in middle school (take that, you stupid red Gyarados!) Then, having caught virtually nothing, I decided to wipe my completed save file and play through the game a second time. HeartGold was a fun update, but it seemed to be lacking some of the heart of the original for some reason. The battle against Red was still epic, though.

Super Mario Kart
Times played through: 4
This is one of those gray area ones I was talking about. Technically, my dad and I played this about 100,000 times. But we usually played Mushroom Cup on 100 or 150 cc for a moderate, but not ridiculous, challenge. It’s tough for me to classify beating Mushroom Cup as beating the game, so instead I’m going with the number of times we beat 150 cc Special Cup, where the AI is ruthless. This number would probably be higher if I didn’t main Koopa Troopa, because maybe then I wouldn’t have gotten knocked off the track on Rainbow Road EVERY SINGLE TIME I GOT TOUCHED.

Super Dodge Ball
Times played through: 6
It’s hard to argue with the formula of Super Dodge Ball — stand on opposite sides, give everyone a special throwing power and some hit points, and go to town. I’m listing the original NES game, although I also poured a lot of hours into the Game Boy Advance release about a decade ago. The NES game had a familiar River City Ransom feel to the characters, and after you traveled the world and beat all the appropriate teams, you had to face off against the shadow version of your own USA team. Take that, shadow Sam!

Tales of Symphonia
Times played through: 7
This is actually quite the accomplishment when you consider that Symphonia takes around 60-80 hours to complete, depending on how many side quests you do, how much of the optional coliseum you beat and what difficulty you’re tackling on a New Game +. This was my first experience with the Tales series and its frentic, active battle system. We stayed up way later than we should have one summer beating the game for the first time, getting tricked by a false ending toward the end and pushing forward to beat the game until like 5:30 in the morning.

Star Fox 64
Times played through: 8
There’s a reason why I can recite half of the lines in this game from memory, and it’s from sheer repetition. Sometimes it was fun to just boot up the game and play the first couple levels, but this number represents the number of times I showed Andross that he didn’t have the power to rule over Lylat.

Link to the Past
Times played through: 11
It’s the best Zelda game in the series and easily in the conversation for the best game ever, but I can respect that other people have other opinions. Here’s something you can’t debate: This is one of the easiest Zelda games to replay. I can probably tackle this game in four or five hours thanks to knowing most of the item locations and boss strategies by heart. Even I tried that approach in, say, Skyward Sword (which I’ve only beaten once), there’s simply too much story and other stuff jammed into today’s games to make quick playthroughs viable. While the evolution of graphics and plot and characterization are almost always a good thing, this is one example of why it’s not.

Chrono Trigger
Times played through: 19
I’ve achieved each and every one of the endings, including the new stuff introduced by the DS remake (which makes a sad attempt to try to fill in the blanks between Trigger and Cross as though I’m ever going to acknowledge Cross as a sequel). It’s my pick for the best game ever, so I can’t imagine this number surprises you. I still prefer the SNES version for a few reasons, such as the original English translation and all of its quirks. Let me put it this way: if my number is 19 more times than you’ve beaten the game, you’ve screwed up something in your life.

Left 4 Dead
Times played through: 26
This is a guesstimate that is sort of similar to the Super Mario Kart rule — “playing through” this game could technically count for any completed mission (yes, even Crash Course), but I’m limiting it to escaping alive on Expert. As always, I’m a sucker for co-op, and the well-constructed experience of Left 4 Dead keeps me coming back for more even after years (and a sequel) have passed.

Final Fight 2
Times played through: 174
…And now for the shocking number. My dad and I played this game for hundreds or thousands of hours when I was younger. I don’t even know where we originally got the game, but it quickly became one of our favorites. Co-op play was obviously a bonus, as were limitless amounts of spinning piledrivers. It got to the point where we probably knew exactly which group of enemies was coming next, and we introduced mini-games such as “Andore Tennis,” where we could stand on opposite sides of the screen and slap poor Andore back and forth between us until he died. Final Fight 3 was a superior game (except for the slowdown with two players), but I never actually owned a copy — I was stuck with rentals or pirating other means. So Final Fight 2 takes the cake.
I’m looking to purchase the DS version of Chrono Trigger soon. Aside from you, my friend and cousin have endorsed the hell out of this game and have urged me to play it. The only issue I will have is finding the time to get all the endings in this game. It’s a shame when I can’t replay games because my time is limited or I want to play a newer game that got released.