I would be interested to know which computer or video game you think is the saddest. For me it's Minecraft, because when everything gets too much for me in everyday life I withdraw and cry out.
Heavenly Sword had a few very touching moments.
Side fact: Gothic has been patched and the Steam version now runs on Windows 10. That's one less reason to cry.
I had to cry at the end of Telltale's The Walking Dead Season 1.
Undertale
Minecraft though you can't really call that howl.
When I sometimes see these nostalgia videos on YT, I sometimes wish everything was as it was before.