System32 Roulette is a drinking game where you get a fresh install of Windows 98 on some crappy Pentium 2 in your friend's mom's basement. Each player takes a turn deleting a random file out of System32 (we disabled protections, I forget how), then reboots and tries to play a game of minesweeper. If you can, everyone else takes a drink. If you can't, you finish your drink and the game starts over with a clean install.
I really ought to formalize it and make a container based version of the game. But it's far more fun to do on a real computer from the era.