The one that will forever haunt me, is the race in Grand theft Auto Vice City, to get the getaway driver. His car is better than yours, and the cops leave him alone. To make it worse, I've replayed Vice city several times.
Also, the carrier landing missions in FSX. I only got it right once.
Several levels in littlebigplanet.
There are many more, but I can't think of them at the moment.
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