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

@tomaswv 

Hirth Martinez: Hirth from Earth and Big Bright Street. (released 1977)

Mary Chaplin Carpenter: Stones in the Road and Come On, Come On  (released 1994)

Phil Ochs: Rehearsal for Retirement and Pleasures of the Harbor (released 1969)

I believe the OP said the "best American music in the past 25 years.

@rpeluso: Your reminder of Merle Haggard compels me to admit I failed to keep up with this major American artist in his later years. And to admit that I had forgotten---but was reminded by other posters in this thread---of the last series of albums Johnny Cash recorded, perhaps the best of his life.

But how on Earth did I neglect to include Bob Dylan?! I fully understand those who can’t tolerate his current "craggy" voice, but that doesn’t in the least bother me. His 2000’s albums are amongst my favorites of his, and that’s saying a lot.

His early-2000 show at the Pantages Theater in Hollywood was one of my lifetime favorites, and I’ve attended many. I had last seen Dylan ten years earlier, and he was dreadful (so was his 3-pc. band), amongst the worst of my life. Oh that Bob! ;-)

Not expert in any of the following but have heard decent work from them:

Rival Sons, Black Label Society, Kenny Wayne Shepard and the best living blues guitarist, John Mayer.

 

Definitely Buddy and Julie Miller and I'll add Sarah Jarosz. Her albums really sound beautiful.