Good headphones

Hey everyone, little brother wants headphones for Christmas and I am kind of curious of the options out there. I don't know the first thing about audio, so I thought this would be a good starting point. Can anyone give me a few options for good headphones at a 25, 50, and 75 dollar price point? Is the gain in performance comparative to the price? Like if I spend 50, will it be twice as good as a pair of 25 dollar headphones?

Any suggestions welcome at the 25ish to 75ish range. And if you could tell me why they are good I owuld appreciate that as well. I would love to learn a little about it!
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