The best of Wes Montgomery: Five essential albums by the eternally influential guitarist

Like Charlie Christian before him and George Benson to follow, Wes Montgomery reinvented jazz guitar. Each of them dominated the field in their respective eras.

Born in Indianapolis in 1923, Montgomery stumbled upon Christian’s music with Benny Goodman’s band and discovered the world of possibilities of the guitar. While not a hub of jazz, the thriving hometown scene allowed Montgomery’s talent to flourish. Coming up with a style of invention based on necessity, he woodshedded at home, playing quietly without a plectrum into the wee hours so as not to disturb his sleeping family.

It was exactly the result of these circumstances that made Montgomery so unique. His technique sans pick gave his tone a distinctive warmth, while his use of octaves and block chords made his single guitar sound like an orchestra. When it was time to play single-note runs, his fluidity showed mighty jazz chops with a bluesy feel.

Montgomery rose to world prominence and unprecedented success performing and recording with so many other greats, including Cannonball Adderley, Charles Mingus, Quincy Jones, Percy Heath, Jimmy Smith and John Coltrane. He even crossed over into pop and found his way onto the Top 40 charts. Throughout his relatively short career, the man never stopped developing musically, from his early years with organ trios and smaller combos to the lush arrangements created by Claus Oogerman in the 1960’s.

Wes Montgomery’s legacy continues to be felt today. Next time your favourite jazz guitarist plays with octaves, you can smile knowing you’re hearing his enduring influence. If you want to dive into the music of Wes Montgomery, these five albums are a great way to start.

The Montgomery Brothers in Canada (1961)

Wes was part of a musical family. From 1957 to 1961, he and his brothers — pianist and vibraphonist Buddy and bassist Monk — played and recorded as the Montgomery Brothers (and, for a period, the Mastersounds). It’s fascinating to hear the brothers in Canada on this LP, recorded at the Cellar in Vancouver. It’s also a chance to hear Wes with his siblings before all the hits came along.

Movin’ Wes (1964)

This is classic middle-period Montgomery. The varied material is well-chosen: In and Out and West Coast Blues are originals, but any track will get you there. Theodora is a blues ballad of the highest order, and Caravan will blow your socks off. Hearing an electric guitar in a big-band context is especially thrilling, with call and response between Wes and the band.

Tequila (1966)

With producer Creed Taylor, Montgomery takes the titular quirky hit by the Champs into the realm of jazz and bop. Tequila won high praise from critics of the day thanks to Wes’s original compositions like Bumpin’ on Sunset and his masterful handling of ballads. Here, Wes also upped the octave ante by utilizing doubles: the same note played in three octaves.

A Day in the Life (1967)

Oftentimes a jazz musician’s success brings critique that perhaps they had sold out and gone commercial. At this stage of his career, Wes Montgomery outwardly shrugged it off and continued to make beautiful music. On the title track, we hear a Beatles opus reimagined with lush orchestral jazz backing, arranged by Claus Oogerman.

Wes and Friends (1973)

This double-album co-led with Milt Jackson and George Shearing is pure jazz in a combo setting. Stairway to the Stars is heavenly. The sound here is wry and dry with only the musicians and their dialogue. Here, Wes Montgomery’s sound is noticeably brighter than many jazz guitarists, thanks to his exclusive use of the top-of-the-line Gibson L-5CES with its solid spruce top that gave more highs. The album cover shows the artist and his axe in all their glory.

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