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Review: Craft Recordings’ OJC Reissue of Wes Montgomery’s Boss Guitar Hits All the Right Notes

Craft’s OJC reissue of Wes Montgomery’s Boss Guitar delivers a clean, balanced AAA presentation with strong pacing, tight trio interplay, and excellent clarity.

West Montgomery Boss Guitar Original Jazz Classics Vinyl Album Reissue

Craft Recordings is closing out 2025 by emptying the clip on the Original Jazz Classics series—seven new AAA reissues hitting vinyl and hi-res digital between October 24 and December 5. It’s a lineup that covers serious ground: Hank Mobley’s Jazz Message #2, Wes Montgomery’s Boss Guitar, Art Pepper’s Surf Ride, Sonny Rollins’ Plus 4, Yusef Lateef’s Jazz Mood, and two Red Garland Quartet essentials, Soul Junction and After Hours, backed by Thad Jones, Frank Wess, Kenny Burrell, and Mal Waldron.

If your wallet wasn’t already bruised from this year’s avalanche of jazz reissues, Craft just gave it another reason to whimper.

This round also marks the first time Savoy titles from Yusef Lateef, Hank Mobley, and Art Pepper join the OJC family—a smart expansion for a series that has quietly become the most consistently reliable reissue program in the game.

Every release is cut AAA from the original tapes by Kevin Gray at Cohearent Audio, pressed at RTI, and wrapped in tip-on jackets that actually respect the originals. And yes, the 192/24 hi-res drops hit the same day as the vinyl—because someone at Craft still believes in doing things properly.

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And then there’s Wes. Only Montgomery—GRAMMY winner, melodic assassin, and the guitarist both Stevie Ray Vaughan and Jimi Hendrix openly worshipped—could title a 1963 album Boss Guitar and actually mean it.

Wes Montgomery (1923–1968) didn’t arrive in jazz the usual way. Born in Indianapolis, he taught himself guitar at 19 after hearing Charlie Christian at a dance and spent the next year woodshedding by copying Christian’s solos. He never learned to read music, but it didn’t matter—his thumb-picked attack and octave-heavy phrasing gave him a sound no one else had.

Before long he was playing local clubs at night while working day jobs, eventually catching the ear of Lionel Hampton, who hired him in 1948. Montgomery spent two years on the road with Hampton—driving himself between gigs because he hated flying—before returning home to raise his family and play the Indianapolis circuit. He worked with his brothers Buddy and Monk throughout the ’50s and early ’60s, forming a tight unit that moved between hard bop, soul jazz, and post-bop.

His Riverside years, including Boss Guitar and Portrait of Wes, captured him at his most agile and exploratory. When he left for Verve in 1964, producer Creed Taylor steered him toward more pop-leaning instrumental records that brought mainstream success, even if the shift divided purists. By the late ’60s his sound would quietly shape early jazz fusion and, later, smooth jazz.

Montgomery may have recorded Boss Guitar in 1963 for Riverside, but nothing about it feels like a relic. The original composition “The Trick Bag” still steals the entire session—a sharp, swaggering masterclass in cadence and control. His agile take on “Besame Mucho” reshapes a familiar Latin standard into something feather-light yet surgically precise, while “Dearly Beloved” and “Days of Wine and Roses” showcase his melodic phrasing without ever slipping into lounge-jazz autopilot. Even the more relaxed readings of “Canadian Sunset” and Ernesto Lecuona’s “The Breeze and I” carry a quiet authority that only Montgomery could get away with.

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The originals hit just as hard. “Fried Pies” remains one of Montgomery’s most infectious blues vehicles, pushed along by Jimmy Cobb’s unflappable swing and Melvin Rhyne’s understated but essential Hammond work.

Sonically, this reissue lands where it should: clear, clean, detailed, and full of rich tone. It is not the most spacious Riverside recording and everything stays relatively tight in the mix, but the pacing and interplay keep it engaging. It also avoids the modern trap of pushing the music into your lap. What you get instead is a natural, balanced presentation that lets the trio do the work.

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Montgomery’s career was short, but the blueprint he left—thumb, octaves, and unmistakable feel—remains one of the most influential in guitar.

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