Reddit reviews The Complete Hot Five & Hot Seven Recordings

Duke Ellington - Money Jungle Trio album with Max Roach and Charles Mingus. The interaction between the three is stunning.

Dizzy Gillespie - Sonny Side Up Sonny Rollins was notorious for half-assing his way as a sideman, so Gillespie called Sonny Stitt for the gig too and had Rollins take the first solo on the rhythm changes Eternal Triangle. Epic tenor battle ensues. By the end they're copping each other's licks while they're trading fours.

Lester Young with the Oscar Peterson Trio No one plays like Prez. I Can't Get Started is a standout.

Ella and Louis Two of jazz's greatest icons making definitive versions of standards. There's so much humor and music throughout these recordings. It's worth noting it's the Oscar Peterson Trio with Buddy Rich backing them up.

...And His Mother Called Him Bill Recorded by Ellington's big band in 1967 for the death of Billy Strayhorn, longtime writer and arranger for the band and Ellington's musical other-half. All star ensemble featuring Johnny Hodges, Paul Gonsalves, Cootie Williams, Clark Terry, and Sam Woodyard, to name only a few.

Louis Armstrong - Complete Hot Fives and Sevens About as close to the beginning as you'll need to know for an introduction. This is a good reference point to have as you explore jazz.

This list is already too big. Make sure you hit some Miles Davis too, as has been suggested. Kind of Blue is the sort of album you could listen to all throughout your life and you'd learn something new from it each time you put it on. Art Blakey had some of the best bands throughout his career, as he was always bringing up the young guys. There's just too much!