How about when you watch someone jump and fall into a bottomless pit 15 billion times. This is mainly with platformers. Its like, "Come on, jump when you get to the ledge. Not 20 feet before."
For me, the series that I've played religiously was Halo. I played the hell out of the first one and beat all three of the campaigns on Legendary. Also I played and beat all of the Call of Duty games (minus the shitty ones) on Veteran.
I absolutely HATE meaningless challenges/time trials in any game...it's hard for me being such an achievement whore. I hate saying "Ok...I'll give this challenge/time trial a try" and then ending up in the fetal position, having hit the retry button 30 billion times and still a point or a second off from getting that fucking gold metal!