I can think of plenty, like Kyousuke from Little Busters and Bernkastel, Lambdadelta, Erika and Dlanor from Umineko... but let's go with someone else.
 Nagito Komaeda
Nagito Komaeda from Danganronpa 2: Goodbye Despair.
Danganronpa for the most part is simple entertainment for me. Going through the daily life phases and solving murder cases with incredibly hammy trials is just so much fun. Both the pinnacle of this and also the sole hint that Danganronpa could be something so much more comes in the form of Nagito Komaeda, your best friend and sidekick in Danganronpa 2.
Anyone who's played the first game will probably immediately notice the same thing about him. The look, the voice actor, the ultimate talent... it's obvious, really. But Danganronpa likes playing with your expectations, and this is where Nagito shines. A lot. He is what single-handedly made Danganronpa 2 into the enjoyable experience it was for me. He manages to be simultaneously an incredibly interesting character and also the kind of character who puts a smile on my face with literally every line of his. I think the best way I can think to describe him is like this: He's an Umineko character in Danganronpa.
And that's awesome.