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I suppose mine would be pretty recent. In Banjo Kazooie: Nuts 'N' Bolts, there is a challenge where you are riding in a u.f.o., and are attempting to shoot a shit load of balloons, while travelling very fast. The weapon that you use is not very accurate, and it's somewhat difficult to control.
I spent six straight hours doing nothing but repeating this challenge over and over again, until I finally got both the jiggy and the trophy. The relief when it finally happened was unbelievable.
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I tried it and failed a few times, and won by a fluke.