If you’ve already read my Charles Mingus Top 10, I apologize for the redundancy in this paragraph! I am, for the third time, teaching a course on the music of Thelonious Monk and Charles Mingus for Wesleyan University’s Graduate Liberal Studies program, and as in the previous iterations, it gives me the impetus to listen to a LOT of their music, often falling back in love with things I already dug but haven’t listened to in a while. Inevitably there are some things that I keep listening to intensively well after the class is over, so I figured this time around I would make a couple Top 10 lists of some personal favorites.

There is so much Monk that has inspired me that I could have easily had a Top 10 for his Blue Note, Prestige, Riverside, and Columbia studio recordings, one for his live performances, one for his sideman work – you get the idea. Ultimately, as with the Mingus list, I chose ten tracks that I love and that covered enough ground that most of what I love about Monk is in there somewhere. So here they are, in chronological order.

1 ) “Introspection” from Genius of Modern Music, Vol. 1 (recorded 1947)

For the lone piece representing both the 1940s and Monk’s Blue Note tenure, I chose this way-ahead-of-its-time composition rendered authoritatively (no mean feat for this tune) in a trio with Gene Ramey on bass and his longtime friend and collaborator Art Blakey on drums, who navigates the twists and turns in a seemingly effortless manner. I actually became familiar with this tune from two non-Monk albums (gorgeous versions by Geri Allen and Steve Lacy) before digging into this one and the version from 1971 that provides an apt bookend to his recording career as a bandleader.

2 ) “Mohawk” from Bird and Diz by Charlie Parker and Dizzy Gillespie (recorded 1950)

There are numerous great examples of Monk playing as a sideman in others’ bands both before he emerged as a bandleader and after (this is where I shout out Clark Terry’s In Orbit record as a particular favorite). To my ear this track is the most dramatic early example of him going “full Monk” in a sideman context – his comping and especially soloing display little attempt to conform to bebop orthodoxy (and yes I realize that that’s a somewhat oxymoronic term).

3 ) “Little Rootie Tootie” from Thelonious Monk Trio (recorded 1952)

Here’s Art Blakey again, alongside the otherwise obscure bassist Gary Mapp, on Monk’s first session for Prestige Records. I nearly picked the ebullient original recording of “Bye Ya” from the same session, but this track (written for his son, who was two as of this recording) to me represents an opportunity to hear Monk’s piano playing at an unprecedented level of uninhibitedness. The Prestige sides are the last ones I began to seriously study, but his piano work is highly recommended throughout this period, especially if you are not squeamish about out-of-tune pianos.

4 ) “I Let A Song Go Out of My Heart” from Thelonious Monk Plays Duke Ellington (recorded 1955)

This album represents Monk’s move to Riverside Records and, famously, producer Orrin Keepnews’ strategy to soften listeners to him by presenting him playing familiar repertoire. The results were effective from a marketing standpoint, but this is also just gorgeous music, thanks to Monk’s sensitive and well-informed relationship with Ellington’s music and to the lovely contributions of bassist Oscar Pettiford and drummer Kenny Clarke. Several of the tracks here are among my favorite renditions of Ellingtonia, including this one (sorry Duke, but I actually go to this version of “I Let A Song Go Out of My Heart” first).

5 ) “Brilliant Corners” from Brilliant Corners (recorded 1956)

After two albums of others’ tunes, it was time to unveil unadulterated Monk, and what an incredible document of that this album is. This wonderful and highly challenging tune keeps listeners and musicians alike on their toes, and the solos by Sonny Rollins on tenor saxophone and Max Roach, switching from drum set to tympani for his solo, are among their respective highlights, as is the alto saxophone solo by the less-heralded Ernie Henry.

6 ) “Monk’s Mood” from Thelonious Himself (recorded 1957)

This is one of my favorite recorded tracks, period. The rest of the album is vintage solo piano Monk, including gorgeous renditions of standard ballads, a long, enjoyably meandering blues, and a landmark version of “Round Midnight” (which, when reissued on CD, also included a long track of the various in-progress takes that led to that final version). But then there is this one track also including bassist Wilbur Ware and tenor saxophonist John Coltrane, two and a half iterations of the “Monk’s Mood” melody (debuted on Blue Note ten years prior) with no solos to speak of, save for a few measures of Coltrane flourishes when he enters. There are other landmark recordings of these three alongside drummer Shadow Wilson (it seems like heresy not to include any of the three songs from their studio session or anything from the posthumously-unearthed Carnegie Hall concert) but the soulful purity of this track has been my balm on many occasions (including periods in college where I would put this track on repeat to ease anxiety so I could sleep).

7 ) “Blue Bolivar Blues” from Monk’s Dream (recorded 1962)

If I could just include every quartet track on the Monk’s Dream and Criss-Cross albums, I would, as the sheer amount of groove and joy emanated by the quartet of Monk, tenor saxophonist Charlie Rouse (who many, me included, have anointed as Monk’s most important band member), bassist John Ore, and drummer Frankie Dunlop. Ultimately I picked this tune as a) it exemplifies his groove, playfulness, and pursuit of thematic development in a particularly satisfying way, and b) I needed to have one example of Monk playing a twelve-bar blues tune in here, having omitted such important and brilliant examples as the Miles Davis recording of “Bags’ Groove” and Monk’s own “Raise Four,” “Blue Monk” (especially the Carnegie Hall version with Coltrane and the Johnny Griffin-bolstered version from Thelonious In Action), and “Monk’s Point” (the first Monk track I studied as a teenager), among others of course.

8 ) “Gallop’s Gallop” from Live at the It Club (recorded 1964)

I knew I needed at least one track in the “holy cow, this melody is really hard to play” category also populated by “Trinkle, Tinkle” and “Four In One.” This relatively-overlooked tune (debuted on a Gigi Gryce session nine years prior and not recorded in a studio session again by anyone until well after Monk’s retirement, though Steve Lacy subsequently made it his own with multiple lovely interpretations) is one of those chops-busters, and like the other two cited here is also a heck of a lot of fun. This posthumously-released album (which is delightful throughout) is also one of the first recorded documents of Monk’s most longstanding and prolific group, the quartet with Rouse, bassist Larry Gales, and drummer Ben Riley.

9 ) “Boo Boo’s Birthday” from Underground (recorded 1967)

Another ode from Monk the parent, this tune is a good embodiment of how a Monk tune could be catchy and tricky at the same time. The same quartet as on the previous track is heard here making it sound easy (since in their hands it so relaxed and effortless) but let me tell you, it isn’t! Someday maybe I’ll record my tribute tune for Ben Riley, written over this form/chord progression, but ultimately the real tribute is in listening to him anchoring this incredibly swinging performance.

10 ) “My Melancholy Baby” from The London Sessions (recorded 1971)

That Monk’s last years of playing are so sparsely documented is both unfortunate and telling about what the scene was for acoustic jazz in the United States in the 1970s. This makes the 1971 London sessions (solo and trio with his “Giants of Jazz” rhythm section-mates Art Blakey and Al McKibbon) all the more important. It also adds to his vast catalogue of solo piano renditions of standards, which is a vitally important part of his oeuvre and also just a wonderful way to hear these tunes. If you love Monk (as obviously I do) then hearing him interpret anything is a treat, but there’s an added layer to hearing him do so with songs that are already somewhat dark by nature, with the dissonance and his pregnant pauses adding an additional layer of pathos to “I Should Care,” “Darn That Dream,” “Everything Happens to Me,” and so on. And so it goes on his sensitive rendition of this song, which he’d played three decades prior with Joe Guy and “Hot Lips” Page at Minton’s (as documented on a Xanadu release of the bootlegs) and recorded with Bird and Diz in 1950.