Best American music of the last 25 years?

@tomaswv 

Hirth Martinez: Hirth from Earth and Big Bright Street. (released 1977)

Mary Chaplin Carpenter: Stones in the Road and Come On, Come On  (released 1994)

Phil Ochs: Rehearsal for Retirement and Pleasures of the Harbor (released 1969)

I believe the OP said the "best American music in the past 25 years.

Unfortunately, but in my opinion, most of the best American music came out in the last century.

With that in mind, I will give you my $0.02.

Green Day "American Idiot"

The Black Keys "El Camino"

Eminem "The Marshall Mathers LP"

Johnny Cash "Hurt"

Tool "Aenima"

Tool "Fear Inoculum"

LP "Lost on You"

LP "Heart to Mouth"

Moby "Reprise"

As to "Bonus points for songs that cover the plight of generations or relevant sociopolitical situations at the time."

I may be off base, but most modern music seems to be just a copy of whatever they think will make them rich and famous.

Soulless, vapid and formulaic are words that come to mind.