John Leslie Montgomery came to the guitar late and by accident. He was born on March 6, 1923, in the Haughville neighborhood on the west side of Indianapolis, one of three brothers who all became professional musicians. Monk played bass, Buddy played vibraphone and piano, and Wes did not play anything at all until he was 19 years old. In 1943 he heard a Charlie Christian record at a dance, bought a guitar and an amplifier, and spent the following year learning Christian's solos off the records by ear, note for note, with some informal help from a local guitarist named Alex Stevens.

Two decisions from that first year defined everything he played afterward. He practiced at night, in a house he shared with his wife Serene and a family that eventually included seven children, and a plectrum made too much noise. He started using the fleshy side of his thumb instead. He found the tone warmer and softer than a pick gave him, and he kept the technique for the rest of his life. The octave playing came from the same period of self-teaching: he would state a melodic line and double it an octave above, a physically demanding move he admitted gave him headaches until he got used to the strain. Layered together, single-note lines first, then octaves, then block chords, those three devices became the most closely studied solo architecture in jazz guitar.

For most of the 1940s and 1950s he was a working local musician with a day job. He welded, he worked for a milk company, and he played Indianapolis clubs at night. Lionel Hampton heard him during a 1948 stop in the city and hired him on the spot, largely because he could reproduce Charlie Christian so convincingly, and Montgomery toured with the Hampton orchestra until around 1950 before returning home to his family. He recorded on the West Coast with his brothers in the late 1950s, in the Montgomery Brothers and around the Mastersounds, but he remained essentially a regional figure well into his thirties.

That changed in 1959. Cannonball Adderley heard him playing in Indianapolis and pushed the producer Orrin Keepnews to sign him to Riverside Records. Montgomery was 36 when he made his first album as a leader, A Dynamic New Sound: The Wes Montgomery Trio, with organist Melvin Rhyne. The record that made his reputation followed in January 1960: The Incredible Jazz Guitar of Wes Montgomery, cut at Reeves Sound Studios with Tommy Flanagan on piano and the brothers Percy and Albert Heath on bass and drums, containing his two most durable compositions, "West Coast Blues" and "Four on Six." He won the DownBeat Critics' Poll for best jazz guitarist in 1960, 1961, 1962 and 1963.

The Riverside years produced Movin' Along, So Much Guitar!, Boss Guitar, the live Full House recorded at Tsubo in Berkeley in June 1962 with Johnny Griffin and the Wynton Kelly Trio, and two summit meetings with vibraphonist Milt Jackson. They also produced Fusion! Wes Montgomery with Strings in 1963, which is worth noting because the string-backed commercial direction usually blamed on his later labels actually began at Riverside, on Keepnews's watch. Riverside then collapsed financially following the death of its co-founder Bill Grauer, and Montgomery moved to Verve.

At Verve he began working with producer Creed Taylor, and the partnership reshaped both what he sold and how he was written about. Movin' Wes (1964), arranged by Johnny Pate, moved more than 100,000 copies, a figure jazz guitar records did not reach. Bumpin' followed in 1965 with arrangements by Don Sebesky. Goin' Out of My Head, released in February 1966 with Oliver Nelson arranging, was built around a Little Anthony and the Imperials hit that Taylor selected; it approached a million copies and won Best Instrumental Jazz Performance, Group or Soloist with Group, at the 9th Grammy Awards on March 2, 1967. Tequila and California Dreaming extended the same formula.

The same stretch produced Smokin' at the Half Note, recorded live at the Half Note in New York in June 1965 with a Van Gelder session that September, backed by the Wynton Kelly Trio, the rhythm section Miles Davis had used from 1959 to 1963. It is routinely named by professional guitarists, Pat Metheny and Peter Bernstein among them, as the record that shaped them most. Its existence in the middle of the Verve period complicates the tidy narrative in which Montgomery abandoned jazz for the charts in 1964.

Taylor moved to A&M in 1967 and brought Montgomery with him, and the three albums that followed became the working template for CTI Records and, through it, for the commercial jazz of the next fifteen years. A Day in the Life was recorded in June 1967 at Rudy Van Gelder's studio in Englewood Cliffs, arranged by Don Sebesky, with Herbie Hancock on piano, Ron Carter on bass and Grady Tate on drums. It reached No. 1 on the Billboard jazz chart, No. 2 on the R&B chart, and No. 13 on the Billboard Top LPs. "Windy," his reading of the Association's single, reached No. 44 on the Hot 100 and was the biggest pop record of his career. Down Here on the Ground and Road Song followed in 1968.

Critics divided sharply over this work, and largely still do, filing the Verve and A&M records as a commercial capitulation against a Riverside "before." The voting record makes that harder to sustain: the same critical body gave him the DownBeat Critics' Poll again in 1966 and 1967, while the orchestral records were in shops, and Record World named him Jazz Man of the Year in 1967. He also continued playing the material live in small rooms without the orchestration, at full length.

On the morning of June 15, 1968, at home in Indianapolis, Montgomery told his wife he did not feel very well, collapsed a few minutes later, and passed away of a heart attack. He was 45 years old, and roughly 2,400 people attended his funeral. He had been a recording bandleader for nine years, made more than twenty albums under his own name in that time, and left behind more than sixty original compositions.

Before he passed away he told Herb Alpert that George Benson would be the next great jazz guitarist and that A&M should sign him. Benson signed with A&M and CTI in 1968, shortly after Montgomery's death, brought in explicitly as the replacement for the label's departed star, and went on to take the commercial model further than Montgomery had lived to. In 1978, ten years after his death, A&M released a Montgomery retrospective titled Roots of Crossover Vol. 1, which is as direct a statement of his position in this music as the industry ever made.

Charlie Christian is the origin point, absorbed off records rather than in person, and Montgomery never disguised the debt. What he built on top of it was his own. The thumb produced a rounder, darker attack than any pick, with almost no transient click, and that tone is identifiable within a bar. Above it sat the three-tier solo structure that became his signature: an opening chorus or two of single-note lines, a rise into parallel octaves, and a final ascent into block chords, each tier raising the density and volume without raising the tempo. Guitarists have been copying that shape for sixty years, and most of them announce it more obviously than he did.

His harmonic language was hard bop, rooted in the blues, and his time was exceptionally relaxed even at speed. The compositions he left behind, "West Coast Blues" in 6/8, "Four on Six" with its repeating bass figure, "Road Song," "Jingles," reward that combination of blues logic and rhythmic ease.

The later orchestral records changed the setting rather than the vocabulary. Working with arrangers Don Sebesky, Oliver Nelson, Johnny Pate and Claus Ogerman, Montgomery mostly stated familiar melodies in octaves over strings and woodwinds and improvised sparingly. That restraint is what critics objected to and what made the records sell, and it is the specific move that CTI Records went on to build an entire catalog around.