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

@cincyjim - Jon Anderson from Yes is American music from the past 25 years?

Doesn't seem like many people on this thread like any American music from any artists who debuted in the past 25 years, just older artists who were/are still around.

I'm not sure that 'represents American music of the past 25 years', which the OP was looking for suggestions for, but good suggestions anyway. 

Sturgil Simpson

Emmylou Harris

But mostly the one everybody's seemingly forgotten -- John Stewart. I listened to the guy for years. Saw him live at the Troubadour, as well as other venues. I learned a bunch of his songs and sang them in a gruff John Stewart-esque folk singer bass-baritone. I was first introduced to him when I won his California Bloodlines LP when I rated the record on a Dick Clark dance TV show.

@cincyjim: Though two of your nominees fit the bill artistically, Roy Orbison died in 1988, Gram Parsons in 1973. Quite a bit longer than 25 years ago! 

@larsman

'Doesn't seem like many people on this thread like any American music from any artists who debuted in the past 25 years, just older artists who were/are still around.'

Which is why I mentioned Goose but most people don't want to know about groups they've never heard of, especially if the band is currently in their twenties.