Might not be the saddest, but it is the first one to come to mind upon reading the title:
I don't know about the absolute saddest but the first thing that popped into my mind was the Ori and the Blind Forest Spirit Tree theme, literally every time I hear it since playing Ori I get a bit emotional. Dang I love those games.
"We were supposed to take care of each other...and we did"
Pokémon mystery dungeon and mass effect also had some good ones too
Hearing this cover in the end credits and just thinking back on the entire game made me bawl.. again
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For me it's this - because what happens to these characters and how somber and sad the cast of the game look when the game is starting up. Until you get to that point in the game, you don't understand why they look that way and it's devastating when you get there and realise that they're all sad for one reason and Tidus has another reason for sounding the way he does.
I don't think there was a better game I could have played as a 12 year old.
Here we go. Fucking devastating.The Last of Us 2 - Ellie "Take on Me" Cover Song
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It chokes me up immediately. Don't even try and reflect on the words and her journey. So emotional.