do I have found that it is ultimately the hard games that give the most accomplishment.
I recently played through Star Wars Jedi Knights II: Jedi Outcast
that game is cheap, it is frustrating, it is hard, and it is unforgiving.
but by Jolly-God I beat that SOB, I freakin' beat, and I felt more accomplishment beating that game from my childhood than I did from most modern-day games.
Donkey Kong Country, which I've also been playing through gradually is also surprisingly tough, but man I really do feel relief and accomplishment when I beat a level (most recently Tree-Top Rock, damn that level was hard >.<)
as for specific events? I don't know, Taking on a Rakk Hive with my friends in Borderlands maybe? Beating Too Human with a friend of mine, or playing through the entirety of Saint's Row 2 with that same friend (We 100% that whole game, took half my sophomore year of high school to do it too, we actually finished it the day 10th grade ended

)
but most of this was at least two years ago, I can't think of anything significant recently, though I don't play games as much lately.