My Little Pony: Friendship is Magic - Image #722,502

Honestly, I actually thought Trenderhoof had a pretty well-executed character. He hit the right balance of 'pretentious hipster' without tipping over into full-on 'scumbag.' It helped make it believable that Applejack wouldn't give him the time of day without making it seem weird that Rarity would like him.

I want to borrow his earpiece.