Best American music of the last 25 years?

Note that Frank Zappa and Steely Dan have zero in common. Frank simply didn’t care about any opinions regarding his complex and often unlistenable compositions, where Becker and Fagan were obsessing over every semitone to come up with funky yet cerebral pop songs that others may actually like. Their stuff still holds up, although for many it’s simply too complex...or something (my wife hates Fagan, but that could be related to some historic personal trauma or something). It’s the alleged modern "Americana" thing that often seems "lame and simple" which is not to say some talented players aren’t utilized like the aforementioned Nels Cline. I’ve worked as a live sound mixer/recording engineer with some astonishing people in the "singer-songwriter" or "folkie" world...Julian Lage (well, maybe Jazz), Anais Mitchell (stunning solo act as well as Broadway musical genius), etc., and recommend these people frequently. That said, when alone I listen to jazz pretty much exclusively, with other stuff sprinkled in. When I heard a "local boy" I’ve worked with for years was touring with Bonnie Raitt (Duke Levine) I had to hear her new album...and it’s great, although Duke ain’t on it. Tres Hombres and Little Feat get some gear pile exposure here and there as hey, they’re just worth it.

currently, my favs are
CHRIS STAPLETON 
NATHANIEL RATELIFF & The Night Sweats
EVA CASSIDY

When I feel like listening to more complex music, it’s often baroque era Classical for me. Try following the musical lines of the four harpsichord’s in J.S. Bach’s concerto for they and orchestra. Bach’s chord progressions (with modulations and use of inversion) have more in common with what you hear in, for instance, Brian Wilson’s "God Only Knows", than are the often pedestrian chord progressions in many modern Jazz songs. Of course Bach was not American, and his music is far older than 25 years. ;-)

A major musical love of mine is vocal harmonies, very rare in jazz music, which is predominantly instrumental. But see, in the playing of many musicians, when they are providing accompaniment for a vocalist, I hear them just itching to get to their solo section of the song. The musicians I love are not thinking about their upcoming solo, but rather about the song, and how their playing can add to the music.

Danny Gatton was a guitarist (R.I.P.) greatly respected by Jazz, Blues, Rockabilly, and Hillbilly musicians. Vince Gill made a compilation tape of Danny’s playing, and when he felt his road band was getting a little too cocky/self-satisfied, he would put the tape on the tour bus sound system. He named the tape "The Humbler". ;-) If you like the guitar playing of Jeff Beck, you should hear Danny Gatton.

Another band I should have included is NRBQ, a true American treasure. Their music contains elements drawn from 1950’s Rock ’n’ Roll and Rockabilly (they made an album with Carl Perkins), Country & Western, Blues, Avantgarde Jazz (keyboardist Terry Adams is a big fan of Thelonius Monk and Sun Ra), Pop, Show Tunes, and everything else you can name. When David Sanborn had them on his TV show, he introduced them as "The best Rock ’n’ Roll Band in the world." They were that, but much more.

     what?     .No Billie Eilish?

A little outside of the time frame but they’re still making music- pixies and early Frank black. Band of horses, beach house, interpol, Luna, metric, Pete yorn, the strokes, QOTSA.