My top six list of worst video games I've ever played (all PC):
1. Robots: the video game - Based on the Disney movie Robots. Couldn't even get past the 2nd level, it was so utterly broken! Textures did not render at all and so you just had a bunch of light blue walls.
2. NHRA Drag Racing - An obvious budget title. Horribly broken.
3. Mall Tycoon 2 - Bad graphics and not much else to do.
4. Deep Sea Tycoon - Not much to do, very boring.
5. School Tycoon - Lots of illogical things in this game, for example: The biggest bathroom only accommodates 4 students, 2 male, 2 female.
6. Tycoon City NY - Yep, an Atari PC game makes the list. Three major problems: First, some textures render horribly. Second, in the "Build NY mode" you can't expand outside the first section due to a glitch that causes the game to crash. Third, you can't lose money, AT ALL. Wouldn't you love to run a business like that? The first two problems were supposedly fixed with a patch, although I never could make it work.
I only still play a few games today, and they are the best in the simulation genre IMO: Zoo Tycoon (1 and 2), as well as Rollercoaster tycoon 3 and Simcity 4. I don't play modern PC games at all, I despise the "pay to win" and microtransaction attitudes most developers have taken up. I always call modern video games "The land of the fee".
I still have a pile of old PC game discs somewhere, just gathering dust. There's probably some more junky titles in there, but I don't feel like sorting through them right now.
There is one old PC game I've been looking for at thrift stores though. I collect CDs and music, and I've been looking for a game called Britney's Dance Beat for the PC. They also made a PS2 and GBA version, but I've been looking for the one for the PC. I know I'll come across it sooner or later, I've seen plenty of cheap looking games and software there!