Hotline Miami
I wouldn't say it didn't click for me the first time, but definitely its gameplay wasn't what I was expecting, I thought it would be purely fast paced just as if it was a Metal Slug with a different view, it turned out to be a fantastic game where you need to think before shooting lol.
I have two very different kinds of games I did this with.
The first was Undertale, didn't really get into it at first and stopped playing it around half way through. However after I watched someone else beat the game I got a lot more into it and finally beat all the main endings. Really liked the story and it quickly became one of my favorites after that.
The other is the Crusader Kings games. I got one of them when I was pretty young through a humble bundle and did not understand how it worked at all. Then near the end of highschool I finally tried them again along with playing Stellaris and thats when I was finally able to figure out how to play them and got super into a lot of Paradox's games.
Mount & Blade
There's a cheat that puts the game into slowmo, and it was the first game that pretty much let you dive into an army of soldiers and take them all down with melee combat. It was glorious.
Plus there was a cheat that would let you teleport, so sometimes your enemies would go rally an army against you, and you could literally teleport behind them and take them on the hills.
Glorious game.
Witcher 3
Was overwhelmed with most of the game mechanics.
Dota 2. First time I played it it was not for me, I only played it to hang out with my friends. Many years later I had an itch for it, so I started playing again. And I haven't stopped. It is an excellent game.
Dragon Age: Origins. Not sure why. I was a big fan of Mass Effect already, and of story heavy RPGs in general, but I stopped this one pretty early on and sat on it for several years. Needless to say, it stuck the second time and now I've played it and the other Dragon Age games multiple times.
Knights Field series. I never could get into them back in the day, but I've been on a retro kick with my Anbernic and got sucked into them. Ended up putting 20 hours so far into the English translation of the first Japanese KF.
Also, Vagrant Story. Pretty much same scenario where I rented it back in the day and bounced off the combat for not making any sense to me. Tried it recently and really dig it. The combat system is really quite clever once you understand it.
Tetrisphere
I'm currently playing through Shadowrun : Hong Kong and really enjoying it. I'm not sure why I bounced off the first time, I played and enjoyed Shadowrun: Dragonfall and Shadowrun Returns but Hong Kong just did not click with me the first two times I tried
Horizon Zero Dawn. The first time I played it I could not get into the tutorial, just felt so bland. Then years later I tried it again, pushed through the tutorial, and it's now my all time favorite video game series.
The Witcher 2. I died so many goddamn times in the intro scene, rage quit, came back years later and thoroughly enjoyed it.
Etrian Odyssey
I tried the demo for the fourth one and just didn't really like or get it. A couple years later Atlus announced Persona Q (which has mostly the same gameplay as Etrian Odyssey) so, I decided to give the demo another try and it just clicked this time. I have no idea why I didn't like it the first time around.
Pokémon Unite
I tried it early on but I felt it lacked the maturity and depth of playing a more serious and in-depth MOBA like League of Legends. I played a lot of Pokémon games throughout the years but it just paled compared to how fulfilling the long-form games and lore of Leagues went.
Turns out I’m a dad now and these shorter, punchier games are both perfect for me and somehow more fulfilling. On top of that they added complexity with Boost Medallions without breaking the game with them. It makes the setup more cerebral because you lose stats as well as gain.
Binding of Isaac
Shattered Pixel Dungeon
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