Difficult. But I don't think Hedwig's death upset him that much.

Did in the book.

And Dumbledor's

Hedwig kept this kid sane for years. Seeing her die was heartbreaking for Harry :(

I personally believe all of the deaths currently listed deeply upset Harry and the only reason I chose Sirius' death is because Sirius is the only one who's death is shown to affect Harry almost just as deeply months later. With the other losses he was able to move on fairly quickly whether due to circumstances of their death or the situation Harry is in at that point. That's my reasoning.

I agree with SUNThingy.

Prob Sirius but looking back Severus too for all the things he did for him and his mum.

I cried when Sirius died :( I was also very sad when Dumbledore died :(

The Twins were always my favourite. I cried and complained for days after I read the seventh book.