Thanks for the invitation! I used a C64 as my only computer in the late 1990s long past its prime, because my mother got a really good deal on a whole set with printer and disk drives and plenty of disks with software (mostly games, from magazines). However, I was still a bit annoyed by the limitations of the system. I guess, if I had had a forth disk, I might have felt different.
In any case, for personal reasons I don't want to explore the C64 more.
But I never had a GameBoy Advance nor a Wonderswan.
Or the TurboGrafx-16 / PC Engine, Nintendo Entertainment System (alt), Commodore 64, Vic-20, Atari 2600, Atari 7800, Apple II/IIe, or Pet 2001 https://github.com/cc65/cc65
Or the ZX Spectrum, TRS-80, Apple II (alt), Gameboy (alt), Sega Master System (alt), and Game Gear (alt) https://github.com/z88dk/z88dk
Note: Some are slightly pre-1999 (all these, I have at least successfully made a "Hello World" with)
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If they're really wanting 1999, that's the 5th to 6th generation console range with Sega Saturn, PlayStation, Nintendo 64, and Dreamcast. (on these, only recommendations, no successful compiled software)
Or, the GameBoy Advance https://github.com/GValiente/butano