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If you want to understand, and I mean REALLY understand, what modern jazz piano sounded like, and SHOULD sound like, when it changed the direction of jazz, you need to listen to, imbibe and meditate on the music presented here by the two main artists that pioneered modern jazz piano, namely Bud Powell and Thelonious Monk.
Powell and Monk freed up jazz from stride and swing, still holding 
on to these two tenets, but adding a harmonic sophistication, rhythmic brilliance and soloing expertise that took jazz into lands that it had never gone before. Every pianist that you hear today, from Mehldau to Jarrett to Hancock to whoever, has been influenced and weaned by these two artists. Here are the albums you need to start with to get the essence of what modern jazz is composed of.
The double disc from 1944-62 includes some the earliest and most essential bebop recordings. His trio sessions from the 40s with Max Roach/dr and either bassists Curly Russell or Ray Brown are still jazz dropping, featuring “Tempus Fugit”, “Ornithology” and “Cherokee”, with 1951’s “Hallucinations” and “Un Poco Loco” still sounding futuristic. There are tons of songs that have since become standards, all debuted here, such as “Bean and the Boys”, “Bouncing With Bud” “Dance of the Infidels, and “The Scene Changes” and only Powell being the pianist that could properly deliver the proper interpretation of “Donna Lee”, “Cheryl” and “Wee”. Besides being a torrential soloist, Powell also was a master of the lyrical ballads, well exemplified on “All The Things You Are” and “It Never Entered My Mind”. Bebop starts here.
The four disc, eight album box set has a tiny bit of overlap, but not enough to make you want to avoid getting both. He recorded prolifically in 1957, mostly in trio format, with gorgeous renditions with bassist George Duvivier and drummer Max Roach of “I Remember April”, “Somebody Loves Me”, “Everything Happens To Me” and “Stella By Starlight”. He digs in deep on “Salt Peanuts”, “Shaw ‘Nuff” and “Woody N You” and shows his adept charms at the blues on “Bags Groove”. In a quartet setting with Art Taylor/dr, Paul Chambers/b and Curtis Fuller/tb, he swings on “Moose The Mooche” and waxes eloquence on “Don’t Blame Me” while displaying the link between bop and baroque on “Bud On Bach”.
Bud did a series of albums on Blue Note during this time, in 1958, with Sam Jones/b and Philly Joe Jones/dr his writing skills are evident on “Monopoly”, “Time Waits” and “John’s Abbey”, and with Taylor/ b and Chambers/b is still in strong form on “Cleopatra’s Dream” and “Danceland”. His last album here is from 1959, with Art Taylor-Kenny Clarke/dr and Percy Heath-Paul Chambers, still sounding strong on “Star Eyes” and “Confirmation”. A tragic figure, his music was a mix of absolute genius holding back absolute agony. Riveting joy.
The other pioneer who is just as influential today, if not more so, is Thelonious Monk. Artists are either influenced by his composing skills, which are revelatory, or his playing, which was revolutionary in their quirky simplicity.
This pair of box sets contains essentially everything you absolutely need to have of Monk, although it stops during his later Columbia years. That is not a biggie, as he started to repeat himself towards the end of his career. His arc of creativity can essentially be divided into 1) early bop/(mostly) trio 2) hitting stride with a variety of small bands and guests 3) settling into his comfort zone.
His pair of Genius of Modern Music albums on Blue Note from 1952 are his ground breaking sessions from the 194s-50s with the original versions of “Well, You Needn’t”, “In Walked Bud” and the eternally covered “Round Midnight”. Ensemble members include Max Roach, Art Blakey, Kenny Dorham, Sahib Shihab and Al McKibbon, with everyone needing to hear the debut versions of “Straight, No Chaser”, “Let’s Cool One” and “Criss Cross”.
From there, Monk moved to Prestige and then to Riverside Records for a series of wonderful trio sessions, featuring a lithe “Bemsha Swing”, a creative collection of Ellington covers such as “Black and Tan Fantasy”, and one of clever reads of standards like “Tea For Two”. Like minded Sonny Rollins comes in for a wonderful album including “I Want To BE Happy” and “Nutty”, while his love affair with tenor players continues here and all the way throughout his career with an album with Coleman Hawkins and John Coltrane, featuring a definitive “Well You Needn’t” and classic quartets with Coltrane as on “Ruby, My Dear” and “Trinkle, Tinkle”. The same year, 1957, Monk meets with Gerry Mulligan for a surprisingly successful summit that includes a brooding “’Round Midnight”.
At his peak in the late 50s, Monk strips down his work to the marrow on a pair riveting solo album sandwiching his joining up with Art Blakey’s Jazz Messengers for a kindred spirit collection that includes “In Walk Bud” and a wondrously angular “Evidence”. Monk brings in a new tenor in Johnny Griffin, who fits in well on “Nutty” and tears apart a gig in 1960 at the Blackhawk with Harold Land on a wild “Epistrophy”. A one off with a jazz orchestra including Phil Woods is a wild train ride of “Little Rootie Tootie” and “Monk’s Mood” . The last tenor of Monk’s quartet, Charlie Rouse, debuts on the 1961 In France album, with a a rich form of “Off Minor” and Monk in a cute solo take of “Just A Gigolo”. Music that will get under your skin and in your head.