An old game for the Nintendo Entertainment System comes to mind, Gauntlet. This game was based off an Atari game from what I understand, but I only ever played the NES version. The game itself was not particularly hard, but it had 100 levels. Used to play this with my siblings and cousins a lot, but I think the highest I ever got was level 67, after many many hours of gameplay.
If you are a real fan of punishment, give Halo 2 a try. On legendary. Again, not particularly hard but there are several areas in a couple earlier levels where Jackal snipers armed with beam rifles continuously spawn and can kill you with one shot, whether its a body or head shot. If you are in a moving vehicle it takes 2, but even at full speed they can track you and hit you no problem. It basically comes down to memorization and timing, which I could never master on one level. So I eventually gave up. Not sure if it is like this on PC, I've only played it on Xbox. I've beaten every other Halo game on Legendary (except for the RTS Halo Wars), but I could never get the patience enough to do so on Halo 2.