Best American music of the last 25 years?

I’ll add to the artists already mentioned and will recommend the albums I prefer.

Patty Griffin - American Kid

Tom Petty - Wild Flowers

Uncle Tupelo - Anodyne

Son Volt - Trace

Roger Waters - Is This the Life We Really Want

Johnny Cash - American Recordings

Gary Clark Jr - Live

Conor Oberst - Upside Mountain

Better Oblivion Community Center - S/T

And a Whole lotta Wilco, too.

Chris Stapleton - Traveller, From A Room, Starting Over

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.