Not exactly difficult to master/beat but mine are Heroes of might and magic 3 and Diablo 2.

I still play them a few times a year.

It was tilty at times. I had so many -35 games because I messed up one key shot, etc.. I mostly played during season 2 so Kaz wasn't around.

At 30, gaming steadily for 25 years, I've gone through a lot of obsessive phases.

I have played FF7 a huge amount of times (I still think it holds up quite well, despite what people say about being unable to play it due to graphics). Definitely have 15+ days on that one. Probably my top played single player game...

Then FF11 (350+ days played), WoW (140+), TF2 (80+). Played tons of CS beta x.x back in the day up til about 1.6, a game called myth 2 (one of the best RTS ever, in terms of game formats), TFC, Warcraft 3...

FF11 is the one game that consumed me for years. Super grindy, and I couldn't put it down. The only thing that came close to that sense of adventure/achievement was my first 6 months in WoW, which I played obsessively.

MMOs are just a different animal. I'm currently enjoying FFXIV pretty casually.

I can think of three:

1) Getting less than 1:00 on Super Mario Kart, whatever the first map is. Finally did it, which looking at records is actually a pretty damn impressive feet.

2) Speed running Super Mario Brothers. I had no idea what speed running was at the time, but I did it. I thought I was pretty fast, but looking at records (even non-TAS), I wasn't that fast.

3) Beating Adventure Island for NES. This whale got away. I NEVER beat the sucker. Only video game I think of that I owned that I was never able to beat (that I tried to beat). It was just SOOO hard to do. No continues, finite number of lives. What made it really frustrating is I could always get to the same spot, and it took forever, but could never get past it.

The video game challenge that hurt the most to elude me was Project Gotham Racing 2 All Platinum. An acquaintance and I had duelled over who was best at PGR1, with him generally having the edge both head to head and on records. When the sequel came out we bet $50 - the price of the game and an amount that meant something to me - to see who would be the first to clear it.

I was able to take a strong lead, and even hold it as we got to the end stages of the game where medals became days or weeks apart. Unfortunately I got stuck on a speed camera and just couldn't figure out how to pass it, and when he got that medal I knew I was probably done for. Sadly I don't think I have the kind of free time it takes to remaster that game just to try again.

This story may be familiar to some of you; I've told it before.

In the spring of 2001, I played a short season of the original NBA 2K for the Dreamcast. I played it in my college dorm room, generally in the afternoons while my suitemates were at class. The season was 20-something games, probably 2-3 minute quarters (perhaps up to 5 minutes). As the Knicks my record was fine, and I got through the playoffs to the Finals without anything notable happening that I recall.

In the Finals we were up against the mighty Lakers. I was in a lot of trouble after 2-3 games, having lost at least 1 game already and being clearly outmatched.

In many NBA games of that era, it was trivially easy to flagrantly foul somebody (usually the "turbo" button plus the "foul" or "hand check" button or something along those lines). In NBA 2K and in other games as well, if a player is flagrantly fouled he is automatically injured for a minimum of one quarter. Often the injury lasted the full game, and in 2K it was sometimes for multiple games.

At some point in Game 3 or 4, I flagrantly fouled Shaq. He went down and wound up being injured for the rest of the series. I'm not sure whether or not I did it on purpose. My best guess is that I did it semi-intentionally, maybe fouling just a little bit too recklessly in the hopes of making something happen.

In any event, even without Shaq the series went 7 games and my Knicks barely pulled out the victory. So it was a somewhat hollow win, and I still feel guilty about it. Was the flagrant foul debatably a good "strategy" that fits within the rules of the game? Sure. But it feels wrong, clearly, and it's been hanging over my head for 13 years now.

What I need to do to get redemption is obvious, and yet it only occurred to me within the last few years. I have to play a season of NBA 2K1, on the Dreamcast, with the Knicks. The Lakers deserve another shot at me. Perhaps we'll meet again in the Finals and perhaps we won't, but the important thing is that it has to be done.

If I was told I had one year to live, playing the season of NBA 2K1 would be one of the things I'd have to do before I died. I am not being facetious.

That's a white whale.

The 'flee from town' section of Call of Cthulhu. Just couldn't get past it on PC. Didn't even get to see any of the real antagonists like Dagon or Cthulhu or whatever else eldritch horrors you get to see.

I'm generally able to complete challenges. Either that or I just forget them. Probably the two things that have obsessed me the most were finishing every level on N+ and beating everything in Super Hexagon. I shudder to think how many times I would must attempted the most difficult level in Super Hexagon.

Another one was back in 2006 I spent a few months trying to get into the top 10 rankings for Battlefield 1942 on bftracks.net

My dad and uncles have a pretty good one. It involves Strat-o-matic, a super-realistic dice and card baseball game that was invented in the 60s and is still popular today. They started playing the 1968 season in 1969, and played pretty obsessively until my dad left for college in 1974. For every game they played they kept the scorebook by hand. And every week (on the schedule) they would add up all the statistics for the whole league by hand and calculate the batting averages, slugging percentages, ERAs, etc. for the entire league without even the aid of a calculator (my dad got a 36 on the ACT).

They put in a week long marathon session right before my dad left to finish the regular season. They played the playoffs when my dad was home for winter break (they split the leagues in ahistorical 1969 divisions and played the 1969 schedule because they couldn't find a 1968 schedule). And then, somehow, they never got around to playing the World Series. They all went to college, had kids, and moved away from their lol Iowa home. It was looking like the season, on which they had spent literally thousands of hours, would never have closure.

The Giants and the Tigers waited to play each other for 13 years until 1987 family Christmas, when the game was broken out and the season finally finished 18 years after it was started. The Giants won in 6. This series was witnessed by me at age 5. With so much importance being attached to the game, obviously I wanted to be a part. My dad taught me how to play and played with me regularly, leading me to understand concepts like division and probability before I entered second grade.

Note: The Christmas World Series was the subject of one of those cheesey human-interest stories that I was able to find on google! That's how I know so much detail.

Another of mine was the Amiga version (I know it's unpopular to rag on the NES, but the NES had such god-awful sound and graphics compared to the Amiga) of Bubble Bobble. You had a limited number of lives and continues, and I never did beat the damn thing.

Watching the longplay now twenty years later I'm intimately familiar with most of the levels. I made it into the 90s (of a 100 level game) and never realized how close I was to the end.

That music literally haunts my dreams to this day.

Mike Tyson's Punch Out

I never beat Tyson back in the day. I used an emulator to practise against him and a few of the others late in the game. Then, finally, I legitimately played the game from start to finish going undefeated.


Guitar Hero 3 - Through the fire and flames Expert

The only song where I actually practised individual parts, usually I just played the songs over and over. The intro tapping I even practised with the wiitar only. Finally, one day, managed a 3 star finish. Then I discovered Guitar Hero drums and haven't played a single song on plastic guitar since.

I thought Jordan was the bigger Guitar Hero conquest. Although a lot of that has to do with how much better GH2 was than GH3, and how much more difficult the engine was. TtFaF on GH2 engine would be borderline impossible for all but a very very small percentage of competitive players.

Probably my biggest white whale was 5-starring everything in GH2. I can't even remember the last song that I got - was probably either Jordan, Six, or Psychobilly. I really miss those days, Rock Band was fun and everything and a really well-put-together game, but GH2 was the pinnacle of the plastic instrument games and it was all downhill from there.

When I was a little kid who didn't own any gaming systems, it was finishing every exit of Super Mario World. I went over to my friend's house all the time just to play that game.

You should try rock smith.

I guess mine would be wizardry 5? I don't think I ever actually beat it, because I couldn't figure one thing out to get to the end or something. I think this was on the apple 2. That's the only game I recall not finishing and kind of caring about not finishing. I mean I don't think I unlocked everything in Mario kart wii 1 edition, but I never really obsessed about it. I think I made maps on graph paper for that damn umm pah pah room in wizardry 5 (I think it was 5).

You're probably right but my white whale is TTFAF for sure. I remember it being a big thing in the GH community when someone FCed TTFAF for the first time.

Yeah it was. Mostly due to the "snake" which was once theorized as impossible.

Honestly though, the HellAshes days of scorehero and GH2, when everyone still used Ustream, that FC was the bigger deal because that was the first time people had figured out the "tapping" technique to nail Jordan's insane HOPOs. The first tapping video that went up where a guy got like 95% on Jordan was revolutionary on an enormous scale within the community.

Was TtFaF harder? Yeah, it was. And such a perfect song for being the insane conquest song for the game.

After beating Jordan, TTFAF wasn't that hard to pass, except for that damn intro. Was stuck on that damn intro for months. Beat the song first try after that never using star power. I think the 3 biggest conquests for me were Jordan, TTFAF, and...Don't Fear the Reaper on drums. Dear god that cowbell song was insane on drums.

Looked it up because I was curious. Jordan was my second to last 5* on GH2. Six was my last, almost a year later.

I think I should clarify...TtFaF is easier to pass provided you just put in a few hours to learn the intro (which I never did). Jordan is the easier FC

Ultima series was a white whale for me but it's slowly swimming off into the horizon and I'm caring less and less (though there's always a chance it comes back). I played Ultima "0" (Akalabeth), Ultima I and got to the final battle of Ultima II. I need to grind a little bit to be able to finish it, and the entire game plus save (tiny files) has been attached to an email in my Gmail account for over 7 years.

What I really want to play is U7 but I'm not going to play it out of sequence. I don't know if I'll ever get there.

qft

I only really played ultimate 3 and 4, and completed both back in high school. I recall U4 being a very satisfying complete experience at the time. U3 was really enjoyable, too, but U4 really seemed to be just a huge leap forward in a lot of ways. These memories are all pretty fuzzy now though.

Baldur's Gate 2

I didn't read the instructions and rolled a ****ty character. I got as far as the last fight with the big boss but kept dying. The save has followed me across two PC's but I'm not sure the final fight is winnable with the wimpy sweet talking thief I rolled.

Perhaps I'll start again someday.

i never did finish blackthorne.

Yea U4 was considered revolutionary for rewarding "virtue" as opposed to just going around killing/stealing.

Baldur's Gate 1/2 is another one that appeals to me in theory and for a time was a whale, or at least a significant entry on my backlog.

+1 for both of these. Gradius III is a great game, played it multiple times over 20 years but I can't get past that fast scrolling level (level 7?) and I never will.

Descent

Played this game as a kid on a horrifically large Dell desktop in the mid 90's. Absolutely loved it. Anyone here ever play it?

You basically fly around underground metallic tunnels on some foreign planet (very claustrophobic feel to the game) shooting ships and rescuing hostages, and collecting keys. A flight sim FPS with an insane amount of num-pad keys needed for movement ... pretty much forcing you to buy a joystick.