Hmm So Buddy Holly is a dead Early Rock n Roll Musician known for his Nerdy Looks.
Kurt Kobain Was an Acid Bleach Grunge person with a Seattle sensibility. Known for wearing flannel. He would probably be a hipster today.
There is a fight.
Slash is in a Hair Metal band, but of the people in the band he isn't particularly hair metal. He looks like he wanted to be in some sort of Alice Cooper/Ozzy type band but ended up successful anyway. He's an original though. He is Slash-esque
So a Nerd, and a Grunge Hipster battle Slash.
The closest I have tonight is
Revenge of the Nerds?
Highlander?
Across the Universe?
Harry Potter and the Half Blood Prince?
Harry Potter and the Deathly Hallows pt 2?