Best American music of the last 25 years?


What songs and artists best represent American music over the past 25 years?

I am making a mega playlist for my friend immigrating to the States next month. She loves English music but it's heavily censored where she is from. What are the best songs to help her catch up to date on popular genres and show her the best songs of the last 25 years?

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

leon471

Tom Waits???

His music straddles the 25 year cutoff but whole albums are dedicated to his music by many of the artists listed below.

Townes Van Zandt didn't make the cutoff date but his music  is still  going strong as covers

Oops, right you are @larsman! And Leonard Cohen is Canadian, but at least that's "North" American. ;-)

Cadillac Black.

Ryan Bingham

Lyle Lovett

The Killers

Fugazi

Sublime

Black Pumas. 

Samantha Fish. 

 

 

 

I forgot to mention Ryan Adams, an artist that has incredibly strong songs, consistently that connect with people in one second....

Gregory Porter - Liquid Spirit

Chris Jones - Moonstruck

Jonny Lang - Wander This World

Michaela Anne - Desert Dove

+1 Lyle Lovett