Personally there are a few games which left me very dissappointed, after hyping myself up for years in certain cases.
Divinity Original Sin: turns out I prefer more streamlined, less packed games (love Pillars of Eternity) and that coop play in a CRPG stresses me out.
Wasteland 2: I actually managed to finish this one but secretly I admit I was hoping for a better Fallout which I didn’t really get. New Vegas did the cowboy theme much better.
INSIDE: while the design was cool, it was just a ton of boring, easy puzzles in comparison to LIMBO, its predecessor.
I only played S2 after S1 of walking dead.
I remember the best moment of S2 was a flashback to S1. It was just a simple dialogue dialogue between Lee and Clementine, but just that was way more impactful than any other moment in S2. It was a very human moment. That was when I realized how much better written S1 was.
Some of the writers of S1 left telltale to make Firewatch, so that probably explains why S2 and the other seasons didn’t live up to S1.