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.