Gotta go back to Creighton Prep to dig up some gems, Connnor Oberst and Alex Payne:
Saw this dude when he was wreaking havoc on an acoustic guitar in 1991, when I was an undergrad at CU, and he was 11 at Kilgores, famous Creighton bar:
and in H.S. lived 4 houses from this Greek-American wiseguy, one of the best filmakers of the post-millenium age (previously mentioned ELECTION scene at Georgetown):