Getting the "Walk Free" achievement in Grand Theft Auto 4 by accident. That was weirdly hilarious. I smashed my motorcycle, flew into a construction site and was trying desperately to sprint back to the road to get a new car when suddenly my wanted level dropped and i got the achievement. Games quit presenting a challenge for me in 2006 so comedic moments are the only ones i really remember.
But if you want the most impressive, i did once complete the final mission of Saint's Row 2 on the maximum difficulty without any damage being done to my chopper beyond damage i inflicted on it gunning down the pilot before i stole it.
But if you want the most impressive, i did once complete the final mission of Saint's Row 2 on the maximum difficulty without any damage being done to my chopper beyond damage i inflicted on it gunning down the pilot before i stole it.