Naughty Dog is so committed to the bit that, in Uncharted and The Last of Us, they made not only the characters but also the game design look older with each new episode. Snark!
This is an interesting topic. One good example that comes to mind is No More Heroes. (I think about it because NMH3 just got up on the eShop this week.) The characters age pretty much in real time, I believe? At least in relation to when the scripts where written, give or take real life development-related delays. Travis Touchdown was 27 years old in the first No More Heroes and is 37 years old in No More Heroes III. His behavior, concerns and relationship to Sylvia also reflect (or seem to reflect for NMH3) his aging. He is a thoughtless young loser in NMH, and more of a middle-age “what am I doing with my life” desillusioned thirtysomething in TSA and NMH3. He also seems to care much more about his city and the people around him, somehow, in the recent episodes. Which I think is typical of getting older? You start thinking less about yourself and more about “your world”, i.e. the community, city and people around you. Or at least, I feel I relate to that. Maybe I am projecting. Also, his kitten turned into a big fat cat. I am sure you cat lovers out there can relate?
Ryū Ga Gotoku / Yakuza also tried this a bit, I feel? Characters age through the episodes, although not as strictly as No More Heroes. It’s most visible with Haruka, obviously. She is 9 in the first RGG and 19 in RGG6. Kiryū is less obvious, closer to what Naughty Dog did with Nathan Drake for example, but still clearly ages throughout the game. So do several key characters and even some random NPCs. There are also many flashbacks (incl. an entire game, RGG0) that show younger versions of the characters. The most interesting part of RGG might be how Kamurocho itself ages and transforms itself as a reflection of how real life Shinjuku is evolving. Shinjuku’s gentrification, and how it affects marginal people like gangsters, is pretty much the core theme of the series!
Gyakuten Saiban / Ace Attorney also keeps track of the characters’ aging. It’s not as well done as in RGG and they almost killed the series with how poorly they handled Naruhodo / Phoenix in GS4 but they kinda found a rhythm and a better way of handling characters’ aging in GS5 and GS6. For instance, I was surprised how well they handled an “adult” Mayoi / Maya in GS6 and the evolution of her (necessary by convention) “platonic” romantic relationship with Naruhodo / Phoenix. Once again, the aging is more visible with the kids, namely Harumi / Pearl, both physically and psychologically.
There is also the special case of yearly sports games based on real athletes. Not as interesting to discuss as fictional characters but it’s a fascinating “record” of how some real life people have aged. There was that famous viral tweet about Vince Carter a few months ago. Can’t find it but here is a video showing him evolving through NBA2K games. The oldest console he appeared on is the N64 in 1999, and he retired in Summer 2020, just before the release of the PS5 and Xbox Series. However, if you (rightfully) consider the Switch as belonging in the most recent hardware generation, he has indeed appeared in this latest generation of consoles as an active player, until NBA2K20. That makes him one of the most recurring video game characters of the last two decades. Although he surprisingly never crossed paths with Ryu from Street Fighter II despite this long career in video games, he has appeared in a video game together with Mario.