What a winter of centennials – Bags, then Dexter, now a happy 100^th birth anniversary to the extraordinary guitarist Wes Montgomery.

Back when I was a teenager, I used to read guitar magazines and as limited as my own chops on that instrument were (and indeed maxed out at being), I was nonetheless fascinated by “impressive” guitar playing, whatever that means. I would constantly hear people refer to Wes, so eventually I went to Cutler’s records and picked up a copy of the A Day in the Life LP, probably because that’s what they had and because I recognized a lot of the pop songs. I enjoyed his mostly-octaves renderings of simple melodies amidst thick arrangements well enough, but mostly didn’t understand the hype. Then a couple years later (while still in high school and having caught the jazz bug in the meantime) my friend Todd Grunder played me the Incredible Jazz Guitar album and I was absolutely floored by everything about it, ultimately getting it on cassette and wearing it out. So began my subsequent 30+ years as a Wes devotee, which is sadly quite a bit longer than his own career, given his premature departure at age 45.

As with many jazz-adjacent guitarists, I started off identifying him as “they guy who plays octaves,” but the deeper I got into him (and as I more or less ditched the guitar to focus on piano) the more I heard the exceptional and instrument-transcending depth of his musicianship. In chronological order, here is a small sampling of Wes Montgomery music that has particularly knocked me out.

1 ) “Moonglow” by Lionel Hampton (single from Decca Records, reissued on various compilations) (1949)

The days before Wes was a bandleader aren’t particularly well-documented, so this Hamp ballad is a gem – Wes’s wonderful melodic lines around the melody are a bit low in the mix, but listen and you’ll hear the seeds of melodic ingenuity that are so central to his musicianship.

2 ) “Montgomeryland Funk” from Montgomeryland (1958)

This hard-swinging, blues-infused track represents both Wes’s tenure with the Pacific Jazz label and his wonderful musical synergy with his brothers Monk (on bass) and Buddy (on piano here, though also a great vibraphonist). In addition to his burning solo, Wes engages in a lively musical dialogue with tenor saxophone giant Harold Land, not unlike some of the recorded exchanges Harold had with Clifford Brown a few years before this.

3 ) “West Coast Blues” from Incredible Jazz Guitar (1960)

This track from his breakthrough (though not first) album on Riverside Records is perhaps THE go-to example people use to demonstrate the generic Wes Montgomery solo arc, from thumb-plucked single-note lines to octaves to full block chords. That sentence makes it sound ho-hum and the relative popularity of the track suggests that it would be hipper for me to suggest some alternative, of which there are of course plenty. BUT HOLY COW is this extraordinary music, and hundreds (at least) of times listening to it hasn’t diminished its potency at all. It’s elevated further by the wonderfully flowing solo that follows his, courtesy of pianist Tommy Flanagan, a solo that my teacher Ted Dunbar, a friend and disciple of Wes’s, made me learn note-for-note vocally (that’s right, I wasn’t allowed to play it until I could sing the whole thing).  

4 ) “Bock to Bock” from Groove Yard by the Montgomery Brothers (1961)

Previously recorded with a larger ensemble, this gorgeous performance is the definitive recording of one of the definitive songs in the Montgomery lexicon, providing a sort of soul-leaning vision of the sort of chamber jazz intricacy associated with the Modern Jazz Quartet. Wes is the only soloist here, but the groove is expertly tended by Buddy (the composer of this song) and Monk, along with the great Bobby Thomas (another former teacher of mine) on drums.

5 ) “One for My Baby (and One More for the Road)” from So Much Guitar (1961)

I could certainly do an entire top 10 of ballad performances by Wes, and this one is a particular favorite for the way he stretches out and for how subtly yet distinctly he brings the blues into his melodic rendering. Hank Jones, Ron Carter, and Lex Humphries provide wonderfully sensitive accompaniment and Hank gets a short solo of his own.

6 ) “S.O.S.” from Full House (1962)

As an educator, one of the things I find particularly interesting is the way certain musicians, by dint of unorthodox technique or what instrument they play, have less capacity than others to play a million notes per second over sustained periods and yet sound completely assured on up-tempo tunes. The people I most often cite in that regard are Miles Davis, Thelonious Monk, J.J. Johnson, and Wes. I won’t get deep into the woods of the technical aspects of this with Wes’s thumb-plucking technique, but I love hearing him hold court on fast tunes. I nearly picked the live version of “Four on Six” from the record that’s at #8 on this list, but chose this one partly because the reissued version has two takes (which demonstrates even more variety in his lines) and partly because hearing him follow tenor saxophonist Johnny Griffin (one of the great shred-meisters of the era) underscores his command.  

7 ) “Fried Pies” from Boss Guitar (1963)

Wes. Deep, stanky blues. Organ trio with the great, underrated Mel Rhyne. All that stuff needs to be on the list somewhere, and on this performance it all comes together perfectly, with Jimmy Cobb swinging hard on drums, as he does on the previous and following tracks on the list. Aside from the groove and texture, another great thing about listening to Wes playing in an organ trio (particularly with Rhyne, with whom he recorded three Riverside albums) is the opportunity to hear his swinging and tasteful comping with particular clarity.

8 ) “No Blues” from Smokin’ at the Half Note (1965)

In a sense this track (which also sees Wes now on Verve Records) pulls together a lot of what can be heard elsewhere on the list. It’s a blues tune, features great single note lines, octaves, and block chords, feels strikingly relaxed and flowing given the briskness of the tempo, and features the same rhythm section as on #6 on the list, with Wynton Kelly on piano, Paul Chambers on bass, and Jimmy Cobb on drums. In addition to all that (and here’s where I momentarily put my educator/ensemble director hat again), this is an absolute clinic in how a pianist and a guitarist can sympathetically coexist, assertively supporting one another without ever getting in the way. If there is a Venn diagram with people who enjoy straight-ahead jazz and people who like the guitar, I truly can’t imagine anyone in its center not loving this album.

9 ) “Mellow Mood” from Further Adventures of Jimmy and Wes by Jimmy Smith and Wes Montgomery (1966)

Wes and the king of the jazz organ, Jimmy Smith, had a wonderful sonic connection alongside drummer Grady Tate, documented in an exciting big band album and then a trio/quartet (with percussionist Ray Barretto) session from a week later. This driving performance from the latter session also demonstrates Wes’s affection for and command of Latin rhythms – don’t let the song title fool you!  

10 ) “Up and At It” from Down Here On the Ground (1968)

I first heard this tune in a solo performance by guitarist Tuck Andress, one of Wes’s unabashed devotees. The original version has, like much of Wes’s oft-maligned later work, grown on me as I take it for what it is rather than wondering why it isn’t “More Incredible Jazz Guitar Volume 14” or whatever. We hear Grady Tate and Ron Carter again, playing a gnarly funk groove along with Herbie Hancock and some slick orchestral textures arranged and conducted by Don Sebesky. The melodic and rhythmic command that so typified Wes’s style is totally evident here, even in a shorter and more rhythmically boxed-in setting.