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I did play through one of those endurance races on the original PlayStation. I want to say it took me at least four hours. I was maybe a half dozen laps from the end, had a decent buffer in first place that was hard fought, and all of a sudden the screen went black. I looked at the console and THE CAT HAD SAT ON IT AND TURNED IT OFF! I'm pretty sure I literally cried and never played that game again. I'm sooo glad they moved the power button on later consoles.
Hahahaha, this reminds me of the one time my brother did an endurance race at the Laguna Seca raceway. I think it was like 70 laps or something, it was 2 or 3 hours long, the car he had was so fast that we lapped the entire field 5 or 6 times in the race... except for 1 on the cars he found out. On the last 3 laps he decided to do as many burnouts/slides/drifts as he could just screwing around, and at the start of the last lap he was passed by someone and position changed from 1st to 2nd. He never realized that there was one car that he never lapped and because he was messing around, his tires were essentially black on the UI meaning he had no grip at all and could not catch up fast enough to overtake that car. Finished 2nd for messing around.
We tag teamed to do a good half dozen of these in GT2, one being 8 hours. We did shifts to finish it, 2 hours a piece.
For racing games - GT2 is the pinnacle for me, but Forza 4 is next due to the Top Gear integration. Was huge into that show when it came out.
Back to the actual topic question - I can only think of a couple.
Baldurs Gate 2 - I was about 40 hours in and got myself locked into an area that I was way underleveled for and could not return, and back then I had never thought of making multiple saves. I tried restarting a few times but I just couldn't do it all again.
GTA San Andreas - Flight school I think. I failed so many times in the desert that I never finished the game. Only Rockstar game I never finished the campaign.