Streets of Rage Remake is good but I find it harder than the originals, hehe.
There's a ton of old PC games that are interesting, I still have to go through them but the most unique one I found was Missing: Since January. The game connected to the internet, and you had to receive mails and visit sites to progress. A fan managed to reverse engineer and recreate the server, but that project has been inactive for a while now.
GOG has great choices too, like point and click adventure games. I highly recommend playing The Longest Journey, which is one of the best games ever made.
The Last Express is pretty cool too, it was made by Jordan Mechner who created Prince of Persia. The defining feature of TLE are the rotoscoped visuals and the fact that you can turn back time.
Itch.io has interesting content, but I don't know much about it.
However, I downloaded games from it a while back that I want to try in the future.
They are more artsy and experimental, not sure if that's up to your taste.
The names are:
- Discover My Body
- 0_abyssal somewhere
- Don't Make Love (also on Steam)
- Fugue In Void
- Water Womb World
I also have 'You Must Be 18 or Older to Enter', but that one is super short and barely interactive.
I like the ASCII graphics.
If you're interested in the history of the internet, try Digital: A Love Story.