I realize that my Monk album reviews can be a lot for the newcomer to slog through, so here are some subjective points of entry:
Monk’s Dream (Columbia): This quartet album has a friendly vibe, good tunes, and a host of easily appreciable piano stylings, particularly in “Bright Mississippi” and “Bolivar Blues”.
Alone in San Francisco (Riverside): In my opinion, this is the best of Monk’s solo recordings, not too forbidding, not too bathed in stride. In places, he shows a relatively lyrical side.
Thelonious Monk with John Coltrane (Jazzland/Riverside): Not only do you get a couple of Monk’s best tunes in “Ruby My Dear” and “Trinkle Tinkle”, you also get some fine Coltrane tenor sax, along with a taste of the Monk’s Music all star session.
Live at the It Club (Columbia): This two-disc set samples the live quartet sound Monk cultivated in the 1960s. Well recorded, and stocked with several classic tunes, it provides an earful of tenor Charlie Rouse, Monk’s right-hand man during this phase.
Genius of Modern Music, Vol. 2 (Blue Note): The older recorded sound might take some getting used to, but you’re not going to find a more arresting example of how creative Monk was in his early days. With such gems as “Four In One”, “Criss Cross”, “Ask Me Now”, and “Skippy”, this is pretty essential, and you hear some good Milt Jackson vibes to boot.
Brilliant Corners (Riverside): Despite some rough edges, this is an ultimately rewarding alternative to the bop and standards of the time.
Plays Duke Ellington (Riverside): Particularly if you’re a Duke fan, this record is quite easy to enjoy, and it offers a different perspective on Monk’s piano playing.
Monk (Prestige): Once you’re into Monk, I really recommend the complete Prestige box, warts and all, but failing that, this single disc contains one of the best sessions Monk recorded for the label. “We See”, “Locomotive”, “Smoke Gets in Your Eyes”, and “Hackensack” are all played with zest by a band that includes Art Blakey and Frank Foster. The CD also includes some lesser tracks with Sonny Rollins.
Genius of Modern Music, Vol. 1 (Blue Note): Yeah, go for it. Early versions of “Ruby My Dear”, “Round Midnight”, “Well You Needn’t”, and some numbers you won’t find anywhere else, like “Humph” and “Who Knows”.
Straight No Chaser (Columbia): Another of the ‘60s quartet’s finer works, with great versions of “Locomotive”, Duke’s “I Didn’t Know About You”, and the title track.
After those, feel free to roam the catalog, based on tune choice, preferred sidemen, and so on. Monk converts reading this page are probably already barking about this or that omission, and I agree with them, because many other discs might make a great first listen to Monk. I’ve always felt that he never made a perfect album, and he never made a dud, so to some degree, you really can’t go wrong. I think the above choices represent some of Monk’s best work, and they’re all very likeable, so there you go.