Because I'm me, I just have to name a handful.
Bloodborne is the big one. I like to say I've beaten it due to the amount of times I've watched others beat it but have never made it to the end myself. I've played it probably 5 times, getting further every time. I first killed the Cleric Beast on March 6th 2018, first beat Micolash July 6th 2020. Couldn't say why I put the game down again after that other than I did.
Disco Elysium is another. Love the music, the writing, the vibe, how variable your character is...but around the 3rd, 4th or 5th day I feel like the game loses a bit of momentum, or at least it always has for me. I say always have because I've played those first three days with five different characters and still think just as highly of it.
XCOM: Enemy Unknown also stands out in my memory. I've played the first few hours many times, but whether it's losing a high value soldier or just feeling a little overwhelmed in general by one particular challenge or another, I wind up discouraged at some point and just want to start over.
I'll also raise my hand for Final Fantasy VII. For a long time I held a grudge against the game for being so much more popular than Final Fantasy VIII, but one summer in college I gave it one more shot and got absolutely hooked. Unfortunately, one of my common traits with Abby Russell is a tendency to keep a single save file which bit me in the ass when I wound up saved just before the JENOVA fight in the canyon without enough health items to either survive the fight or, more importantly, fight my way back out of the canyon to go grind some XP or hit up a shop. Sucked.
Lastly I'd like to mention Hotline Miami, which is cool as all hell and I still jump back to play the first two or three levels every couple years but that game just feels real impossible to play on a Playstation controller real quick.
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