I don't much care for punishment, with notable exception being driving games. The most frustrating was probably Test Drive 4, in so many ways unfair game. For example there's series of 6 races where same CPU opponent is always fastest, so to tie in points you'll have to win 3 races and be second in the rest. Except... if you tie in points, player loses! You need to win 4 races and be at least second and third in the others - which in that game is a tall order.
That may not be the biggest driving game challenge I've met. That would be Ridge Racer Type 4 (PS1, I played on emulator). Mostly that's just a game of insane grinding - it took me some 3 years to gather all the 320(+1) cars, which is one of my greatest achievements itself. But in punishment department, the highest level 1-on-1 challenges are likely the most difficult thing I've done in racing, or possibly even in any gaming.
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