Since he doesn't like pop, and he wants to be cool, I recommend you introduce him to the most extreme music out there. He'll hate it, but he'll be able to show up all his friends. Bands like:
Napalm Death
Merzbow
Zeni Geva
Godflesh
Arabs on Radar
KK Null
The Boredoms
Throbbing Gristle
etc.
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