Whether it be because it was difficult, fun or a combination of both.
Mine is definitely Dark Souls. After moving into a new SF apartment and having absolutely no money, internet, cable or new games, I finally managed to finish that monster.
My favorite legacy S-rank is probably Vice City because that was probably the most fun I've had playing a game to death. I especially liked how the 100% completion bonus was infinite ammo, being able to recruit 4 "homies" in the mansion (kinda teasing how that'd be feature in GTA: SA) and the fact they went so far to give you "all I got was a stupid t-shirt" wardrobe option. So worthwhile and so much fun between the really classic radio stations (between the 80s music and the crazy dated political commentary) and the overall awesome story, characters, and locale.
More recently I especially loved playing through Deus Ex: Human Revolution, since my first playthrough on that was actually my pacifist playthrough and that was definitely a change of pace in terms of how I played video games. I loved a bunch of elements of the game so much that I played it twice in a row in a span of a few days in the summer.
SUPER MEAT BOY!!!
Probably Super Meat Boy?
You sicken me you fucking sadists. =P
Hmm... I'd have to say Dragon Age Orgins? I've got all the trophies on the PS3 version for the main game and all the DLC. Its not that hard to do all of the achievements but god does it take FOREVER. And there are a few that are a pain in the ass especially in the Darkspawn Chronicles.
I don't have any good S Ranks, really. The three retail games I've got 100% on are Call of Duty 4, Modern Warfare 2 and Forza Horizon, but all of those games were supremely easy to S Rank. I wish I could say The Orange Box, but I'm just never going to get the 10 last TF2 achievements that I need. I've got all of the other achievements for it though, and probably about half of the TF2 achievements, but that only makes up for 89/99. Also had an S Rank in Beat Hazard for a little while, but I lost that when Ultra came out. I'd even gotten most of the Ultra achievements, but my save ended up corrupting in the Steam cloud at some point and then I stopped playing. Actually, come to think of it, Audiosurf is probably my favourite S Rank, even if it's not that difficult.
Edit: Mile High Club is easily the most overstated achievement. Without using any walkthroughs or the like, I was able to beat it within five tries, right after having completed Veteran. If you can beat the rest of the game on Veteran, it's really not that hard. Err, guess I should clarify that a bit though. It's mostly just that MW2's 69 star Spec Ops achievement was way more difficult than Mile High Club ever was.
The only game I have ever S-ranked (although I have 100% a couple games which didn't have achievements) was Final Fantasy XIII-2 earlier this year. And since I did in the first two weeks of release not much of the info was online (I bet doing the full bestiary would be quite easy now but then it was quite difficult - but I did enjoy running around and finding the secret glitch-portal enemies). I don't the achievements are that difficult and the game is shorter than many other JRPGs (so I was still enjoying it a lot when I had finished it and so did them just to keep playing) but I definitely enjoyed doing it (especially liking some of the write-ups that appear in the database when you collect different fragments).
@Demoskinos: I had an S-Rank in Dragon Age before the DLC and have to agree that it's in my top 10 list of all time favourites
@ShadowConqueror: I'm in the same boat I think... S-Ranking CoD 4 was a good feeling because of the Mile High Club achievement and Assassins Creed II just had all those feathers.
Motorstorm Pacific Rift.
It was also super fun to play. It's easily the best Motorstorm game and possibly the best racing game this generation, even better than Burnout Paradise.
I guess Call of Duty 2 because it seemed like the biggest achievement possible in the early 360 days (though I did CoD 4, too).
But I also feel proud of Doom and Contra since I think it validates some of my classic skills. Though Mass Effect 2 was super fun, as were both of the Infamous games.
The Walking Dead. From what people tell me, that's probably the hardest S-Rank ever.
But in a less sarcastic vein, I played Super Meat Boy in Steam and got all of the achievements that are in the 360 version, but as the Steam version has extra achievements that are COMPLETELY RIDICULOUS and I'm never going to get, I don't know if I can actually count it. So if not, probably getting 100% in Spyro back in the days of my youth.
Honestly, I'm most proud that I have never gotten one. I have started trying a couple times just to say I did one, but I have yet to see one that wasn't filled with at least 3-4 really fucking ball bustingly masochistic ones. I play games to have fun and it seems like all these trophies just seem to be about who can handle the masochism long enough to unlock it. That's just not for me. The closest I came was L4D 2. I was at a point where all I had to do was one or two more campaigns on the hardcore realistic mode but then they released a new map and they added in something like 10-15 more. Once I realized it would be something I would have to fight for every 6 months to a year when they put out a new map I just gave up.
J/K. ;) I'd probably say Castlevania: Lords of Shadow, even though it isn't listed on my profile. I don't have all of them because of the DLC, and fuck that stupid last boss. I have a Platinum Trophy, so that counts as an S-Rank to me. Either that or Assassin's Creed 1, because it was quite hard finding all of the flags back in the day.
The Orange Box - Getting gold medals with a 360 controller in Portal...FUUUUUUUUUUUUUU-
Super Meat Boy - Not that bad actually
F.E.A.R. Files - Fuck this game. I dont know why I did it, but I did it and fuck this game.
Final Fantasy XIII - Again, why did I do this?
Bioshock 2 - I hate all video games.
I suppose I'm most proud of Dead Space and Oblivion, because they exemplify what I like about the achievement system. The achievements pointed me in the right directions and make me feel like I've gotten the maximum value out of two games I really enjoyed to begin with.
Meanwhile, completing Call of Duty Classic on Veteran makes me feel like I slept with a skeezy whore. I don't even know why I did it. Looking back, nothing about it was a good idea.
Trials HD was a memorable one because I spent literally all day on the last extreme track and was elated when I finally finished it. Unfortunately it was after the patch that made it easier, so I can never brag about that.
Marvel 3, just because I'm not very good at fighting games and I loved this so I spent a good chunk of time learning how to play so I could actually be decent.
And 1 vs 100 because my friend is missing one achievement and he will never be able to get it.
Not because of difficulty or anything, but I'm most proud to have S-Ranked every Elder Scrolls and Fallout released on xbox360. That's a lot of DLC money :p
Halo ODST was fun to get because those firefight missions really brought out the best in teamwork.
Probably Tales of Vesperia. It wasn't all that hard (at least no where near the difficulty of super meat boy. you crazy motherfuckers who did that have my respect) but it did take a whole lot of time to complete. I ended up having to play through it multiple times. I don't think I've ever done that with any JRPG and I enjoyed all of it. I remember a lot of bombcast listening when I was grinding for grade.
Oblivion, i know the S-rank isn't hard to acquire though it is fairly time consuming. The reason it is the one I'm most proud of is because its my favorite game this generation and remains even to this day the only retail game i have got all 1000 and DLC achievements.
Use your keyboard!
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