Best American music of the last 25 years?

Not much comes to mind, not in the last 25 years..

Most Is garbage....most not all, before I'm crucified. 

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.

Rhiannon Giddens - Freedom Highway

Wow, now that is quite a question. I’ll really have to think about that. I am currently listening to Popsicle Toes by Michael Franks… definitely… oh, that is not in the last 25 years… wow, it is 46 years ago… how did that much time go by?

Three sets of two:

Hirth Martinez: Hirth from Earth and Big Bright Street.

Mary Chaplin Carpenter: Stones in the Road and Come On, Come On

Phil Ochs: Rehearsal for Retirement and Pleasures of the Harbor

These are older than 25 but that doesn’t matter. They cover the waterfront, I think.