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

@bdp24 - do you think the people who played with Zappa actually liked the music, or were they just jazzed by the status of being selected to play with someone with such impossible musical standards?  

@chayro - FZ would have preferred to not have to deal with other musicians at all, and could do all of the music himself, but they didn't quite have the technology he'd have needed in Frank's day... He did like using the Synclavier, though... Your question could be applied equally to Captain Beefheart.... 

I might have missed it here, but gotta add Gil Scott Heron. The revolution will not be televised, Johannesburg, H2O gate blues, winter in America, lady day and John Coltrane … what’s old is new again.

2022 - 25 = 1997 as the cutoff date. Hmmm. Gillian Welch for sure. Tiff Merritt. Chris Thile with Punch Brothers and with Nickel Creek. I’ve attended an Americana music fest since the 1980s and have been fortunate to see a lot of good music and "acts".

Love jam bands too. Umphrey’s McGee, Goose, many would say Phish hit their stride around ’97, others say prior was their better work.

Goose is good, but are like eating all dessert. Spafford is more like meat and potatoes. Nice to hear both. I’m trying to remember when Widespread Panic was in their heyday. Might have been before ’97.

Love all the bands represented here plus jazz like Medeski, Martin, and Wood.

Paul Williams is a musical genius. At 95 years old, he's still writing songs from his basement.