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

Oh that’s easy. She’s the best singer no one has heard of. Eva Cassidy. Died in the middle 90’s, yet left a singing legacy that lives on, still  

Check out her Autumn Leaves, and Somewhere Over The Rainbow on YouTube. Thank me later  

 

Well, I scanned and did not see Brandi Carlile mentioned anywhere.  I fell in love with her when she was getting big from her album The Story.  Now about 10 years later I own every record on vinyl and have seen her live 5 times.  She is the most sincere artist on stage I have seen from 100s of concerts over 30 years.  She simply blows my mind!  Many have never heard of her so if you are one, here is a nice video introduction to Brandi:

 

+1 Brandi

Caroline Spence

Mary Gauthier

M.C. Taylor

Tift Merritt

Bonnie Raitt

Lucinda Williams

Hall & Oates

John Fogerty

Gov’t Mule

Drive-by Truckers

Jason Isbell

Tom Petty

The Black Keys

Rhiannon Giddens

Son Volt

Bill Callahan

John Mayer

Emmy Lou Harris

Steve Earle

Shawn Colvin

Joan Osborne 

Amy Helm  

Ryan Adams 

M.C. Ward 

Sturgill Simpson