Wes Montgomery's Six-String Revolution

Montgomery's second session for Riverside documented a guitarist on the rise

Happy New Year, music lovers, and welcome to the first edition of ‘Listening Sessions’ of 2023.

I hope you have all had a restful and joyous holiday season, and are able to ease into the New Year as gently as possible.

Reflecting over the past year, I am filled with gratitude at how much this space has grown, including an eleven-fold increase in subscribers during 2022. To see an audience emerging for what I am trying to do here: highlight music of long ago that hasn’t often received critical, long-form treatment is incredibly motivating and fills me with thanks for everyone who has seen enough value in my work to allow it to appear in their inbox every 10 days or so. With a New Year upon us, I aim to keep moving, as Billy Strayhorn was known to say, “ever up and onward.”

This edition’s essay takes a look at jazz guitarist Wes Montgomery and his 1960 recording, The Incredible Jazz Guitar of Wes Montgomery, in particular. It is a landmark album for jazz in the early LP era and also advances an argument for Riverside’s—the label Montgomery recorded for between 1959 and 1963—importance as well as of its co-founder, Orrin Keepnews, in chronicling the music in the late fifties and early sixties. I hope you enjoy it.

Coming later this month will be some thoughts on the trailblazing singer-songwriter Ian Tyson, who passed away on December 29 of last year at age 89, focusing on the years of Ian & Sylvia.

Until next time, may good listening be with you all.

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If, in 1960, Blue Note was the golden child of independent jazz record labels, Riverside was its slightly scruffier counterpart. The covers had a more working-class aesthetic than the cool sheen of Francis Woolf and Reid Miles’ creations. The sound was more direct compared to the roomy ambience that was Rudy Van Gelder’s signature. Blue Note's cache has never really attached itself to Riverside, which was founded by Bill Grauer and Orrin Keepnews, an editor and writer, in 1953 and which, through a series of financial woes, went bankrupt in 1964.

Yet, even a cursory look at Riverside’s output up to 1960 makes an unimpeachable case for the label’s—and by extension, Keepnews’—centrality in documenting and nurturing jazz’s maturation. Wooing Thelonious Monk away from Prestige was arguably the catalyzing event that elevated the composer and pianist to his stature as the music’s most enduring mainstream eccentric. The legend of Bill Evans is built upon the foundation of the groundbreaking records he made with Keepnews: album-length statements of devastating lyricism and deep interplay. Other staples of the Riverside family of artists were trumpeters Blue Mitchell and Chet Baker, tenor saxophonists Johnny Griffin and Jimmy Heath as well as altoist Cannonball Adderley. It was primarily through Adderley that Keepnews was introduced to the guitarist from Indiana.

Even by today’s hustle-culture standards, Wes Montgomery maintained a punishing schedule. Ever since he heard a recording of Charlie Christian in the mid forties, who, along with Les Paul, took the guitar from the jazz shadows as a strictly rhythmic instrument to the front of the stage as a solo voice, Montgomery lived two working lives simultaneously: holding down a blue-collar job during the day (most often as a welder) to support his wife and seven children and also playing the clubs at night, usually with his brothers: vibraphonist Buddy and bassist Monk. An entirely self-taught musician, Montgomery spend the better part of 15 years burning the candle at both ends. His exhaustion level was often so extreme that he would suffer blackouts, and while he had a few breaks—a stint in Lionel Hampton’s band and a few record dates—he remained little known outside of his home state of Indiana.

During the fifties, several guitarists emerged as heirs to the innovations of Christian and Paul, including Barney Kessel, Tal Farlow, Jim Hall, Mundell Lowe and Herb Ellis and perhaps most importantly, Detroiter Kenny Burrell whose full-bodied tone and crisp, clear architecture to his lines solidified the guitar’s place as a solo instrument in small-group jazz. Montgomery would represent the next, big step forward.

After Adderley caught Montgomery live, he implored Keepnews to sign the guitarist to Riverside. Adding to the enthusiasm was a review Keepnews read of the guitarist by musical polyglot Gunther Schuller. Montgomery’s first session for the label, an organ trio date with Mel Rhyne and drummer Paul Parker recorded in October 1959, was a persuasive, if somewhat tentative, document of Montgomery’s prowess. A follow-up session, recorded three months later, removed any lingering doubt. It remains a touchstone of the early LP era in jazz and a manifesto of Montgomery’s six-string revolution.

Titled somewhat hyperbolically The Incredible Jazz Guitar of Wes Montgomery, the album is constructed with a level of care that makes clear its purpose to properly introduce the guitarist to his soon-to-be-adoring public. The first side’s sequence of an up-tempo groover followed by a mid-tempo Montgomery original then a ballad and then an up-tempo original is mirrored in reverse, except for one small exception, on the second side. There is also the matter of the musicians accompanying Montgomery.

Switching out the grits-and-gravy sound of an organ trio for the tried-and-true quartet format, the album features bassist Percy Heath and drummer Albert “Tootie” Heath—two-thirds of the fabled Heath brothers of Philadelphia—who bring a firm foundation to the music and a deep simpatico. Even more critical is who was chosen to play piano on the date.

Back in the days before Toronto’s CJRT was rebranded as JAZZ FM91, Ted O’Reilly, host of the station’s flagship program, The Jazz Scene, and one of the city’s most important jazz citizens, shared a shortcut for divining a record’s quality: if it had Tommy Flanagan on piano, odds are it was going to be good. While O’Reilly’s maxim overstates Flanagan’s ubiquity as a recorded musician—if anything, one wishes he had shown up on more sessions—it understates Flanagan’s importance as a pianist of almost otherworldly and uncompromising taste. Indeed, The Incredible Jazz Guitar of Wes Montgomery would not have been the resounding success it was if it didn't have Flanagan as Montgomery’s foil.

There’s a quality to Flanagan’s introductions to the album’s two ballads: ‘Polka Dots and Moonbeams’ and Dave Brubeck’s ‘In Your Own Sweet Way,’ that is romantic without being cloying, sentimental without the saccharine, an expression of deep ardour that unbinds the listener to receive Montgomery’s thematic statements. On the former, he gradually moves away from the melody—one of the prettiest in the Great American Songbook—so that by the bridge, he is unspooling delicate, deeply sensitive variations that culminate in a soaring skip across the fretboard in the return to the song’s A section. For the latter, Montgomery favours chords to state Brubeck’s melody—one of the most beautiful the pianist ever wrote. It is a sign of the astute acumen that is embedded into every note of the album that these two pieces were selected as its slow-tempo serenades. Both are wondrous vessels of lyricism, and Montgomery and Flanagan, each an intensely lyrical player, excel in plumbing their dreamy contours.

An appreciation of the collective force of the assembled quartet is to be found on the opening, brisk interpretation of Sonny Rollins’ ‘Airegin.’ True to form, technique is only summoned when the arc of a solo demands it: Montgomery runs off some fleet single lines while Flanagan dances around Rollins’ theme, each using space to shape their excursion through the song’s obstacle course. Percy Heath’s improvisation has him hewing to a walking gait, a reminder of the unshakable bottom he provides. Albert Heath trades fours with Montgomery, favouring the snare and an extraverted approach.

‘D-Natural Blues,’ which follows, is a funky, slinky exploration of the 12-bar form written by Montgomery and played using his signature octaves in which a note is doubled on two strings while muting the strings in between. It provides a bell-like sound that is the guitarist’s most well-known innovation for the jazz guitar. It would, as his career progressed until his too-early death in 1968 at age 45, increasingly define his playing. It’s not a stretch to suggest that from this single, stylistic tic sprang the pop jazz of the seventies (producer Creed Taylor, who helped propel this movement, worked with Montgomery for the remainder of his career after the demise of Riverside) which then begat the far more divisive offshoot of smooth jazz. Yet here, years before any of this was even remotely on the horizon, the only concern is listening to a blues that focuses on how it can elicit phrases of striking soul that studiously avoid cliché. Flanagan’s opening solo—two choruses in length—takes on its shades while never sacrificing his dedication to lyricism. His second chorus, in particular, begins with labyrinthine runs along the keyboard before stopping cold to fixate on a trill, an unexpected turn that illustrates his absolute originality. Montgomery’s improvisation, double the length of Flanagan’s statement, gets progressively bluesier, his line of thought culminating in a syncopated series of octaves in double time.

He adds an equally individualist take on the Afro-Cuban beat with ‘Mr. Walker.’ The rhythm is subtle and the sense of release in the composition’s bridge is the key to its contagious charm. Montgomery and Flanagan’s improvisations are invigorated by it as is Albert Heath whose cymbal blasts propel their melodic permutations.

Everything about Montgomery, by the time this album was recorded—two days in January 1960—is finely honed. It’s not a surprise as he had put in years upon years of work to build and refine his identity as a guitarist but it’s still startling to realize the extent to which Montgomery’s artistry was rooted in an almost profound sui generis.

Consider two of his most famous compositions: ‘Four on Six’ and ‘West Coast Blues,’ both of which receive benchmark recordings here. It’s found in Montgomery’s writing, chiefly the tip-toe progression of the former and the instantly hummable line of the latter. It’s also present in the lengthy solos he offers on both. ‘Four on Six’ has him spinning variation after variation, each building upon the previous one, the invention unflagging, the conclusion of the improvisation dictated more by the restrictions of the long-playing record than any evaporation of ideas.

‘West Coast Blues’ is the textbook example of how he often used the approaches available to him to create a fully-formed statement with a beginning, middle and end. Over the song’s looping waltz time, Montgomery starts with choruses of single-line runs before upping the intensity level by switching to octaves—fattening up his sound and bringing a more percussive bent. His statement climaxes with choruses of chords, enveloping his bandmates in a cocoon of sound. There’s a progression here that is premeditated but doesn’t feel forced, that overflows with technique but is not designed to simply be an empty exercise in it. It documents an artist on the rise. The closing standard, ‘Gone With the Wind,’ with its five-chorus solo by Montgomery follows the same movement of single lines to octaves to chords as on ‘West Coast Blues’ and if doesn’t reach that improvisation’s heights, the closing riff is the perfect summation to what has just been heard.

There are few albums that I can think of that more thoroughly demonstrate, and ecstatically at that, the promise and potential of an individual musician as The Incredible Jazz Guitar of Wes Montgomery does. Even as I would, if forced to choose, pick Jim Hall as my favourite jazz guitarist (more about him in a future essay), Montgomery would be a very close second. He was an absolute force of nature.