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I'm surprised you call yourself a retro gamer but aren't aware of this website:

Completely 100% free & legal & run by the US Govt for the sake of archival and preservation of older games.

Hi there, you meant thank you.. I knew that page...

The Internet Archive is not run by the US Government.  It's run by a private non-profit organization, and paid for by donations.

Also, it's not actually 100% legal.  It's sharing a lot of software and media that's still covered by copyright, but nobody cares enough to do anything about it (generally called "abandonware").  For example, I just found "Burnout 3 - Takedown" for the original XBox, a game from 2004.  I can guarantee to you that that game is still covered by copyright.