Montgomery was born in Indianapolis, Indiana. According to NPR Jazz Profiles "The Life and Music Of Wes Montgomery," the nickname "Wes" was a child's abbreviation of his middle name, Leslie. He came from a musical family; his brothers, Monk (string bass and electric bass) and Buddy (vibraphone and piano), were jazz performers. The brothers released a number of albums together as the Montgomery Brothers. Although he was not skilled at reading music, he could learn complex melodies and riffs by ear. Montgomery started learning the six string guitar at the relatively late age of 20 by listening to and learning the recordings of his idol, guitarist Charlie Christian, however he had played a four string tenor guitar since age twelve. He was known for his ability to play Christian's solos note for note and was hired by Lionel Hampton for this ability.
Many fellow jazz guitarists consider Montgomery the greatest influence among modern jazz guitarists. Pat Metheny has praised him greatly, saying "I learned to play listening to Wes Montgomery's Smokin' at the Half Note." In addition, Metheny stated to The New York Times in 2005 that the solo on "If You Could See Me Now," from this album is his favorite of all time. Joe Pass said, "To me, there have been only three real innovators on the guitar—Wes Montgomery, Charlie Christian, and Django Reinhardt," as cited in James Sallis's The Guitar Players and in his Hot Licks instructional video. Kenny Burrell states, "It was an honor that he called me as his second guitarist for a session." In addition, Stevie Ray Vaughan, Eric Johnson, Joe Satriani, Jimi Hendrix, David Becker, Joe Diorio, Steve Lukather and Pat Martino have pointed to him numerous times as a great influence. Lee Ritenour, who recorded the 1992 album Wes Bound named after him, cites him as his most notable influence; he also named his son Wesley.
Following the early work of swing/pre-bop guitarist Charlie Christian and gypsy-jazz guitarist Django Reinhardt, Wes joined Tal Farlow, Johnny Smith, Jimmy Raney, and Barney Kessell to put guitar on the map as a bebop / post-bop instrument. While these men generally curtailed their own output in the 1960s, Montgomery recorded prolifically during this period, lending guitar to the same tunes contemporaries like John Coltrane and Miles Davis were recording. While many jazz players are regarded as virtuosos, Montgomery had a very wide influence on other virtuosos who followed him, and in the respect he earned from his contemporaries. To many, Montgomery's playing defines jazz guitar and the sound that students try to emulate.
Dave Miele and Dan Bielowsky claim, "Wes Montgomery was certainly one of the most influential and most musical guitarists to ever pick up the instrument... He took the use of octaves and chord melodies to a greater level than any other guitarist, before or since... Montgomery is undoubtedly one of the most important voices in Jazz guitar that has ever lived-or most likely ever will live. A discussion of Jazz guitar is simply not thorough if it does not touch upon Wes Montgomery."
"Listening to [Wes Montgomery's] solos is like teetering at the edge of a brink," composer-conductor Gunther Schuller asserted, as quoted by Jazz & Pop critic Will Smith. "His playing at its peak becomes unbearably exciting, to the point where one feels unable to muster sufficient physical endurance to outlast it." Wes received many awards and accolades: Nominated for two Grammy Awards for Bumpin', 1965; received Grammy Award for Goin' Out of My Head as Best Instrumental Jazz Performance by Large Group or Soloist with Large Group, 1966; nominated for Grammy Awards for "Eleanor Rigby" and "Down Here on the Ground", 1968; nominated for Grammy Award for Willow, Weep for Me, 1969. Wes' second album, The Incredible Jazz Guitar of Wes Montgomery, earned him Down Beat magazine's "New Star" award in 1960. In addition, he won the Down Beat Critic's Poll award for best Jazz guitarist in 1960, '61, '62,'63, '66, and 1967.
Montgomery toured with Lionel Hampton early in his career, however the combined stress of touring and being away from family brought him back home to Indianapolis. To support his family of eight, Montgomery worked in a factory from 7:00 am to 3:00 pm, then performed in local clubs from 9:00 pm to 2:00 am. Cannonball Adderley heard Montgomery in an Indianapolis club and was floored. The next morning, he called record producer Orrin Keepnews, who signed Montgomery to a recording contract with Riverside Records. Adderley later recorded with Montgomery on his Pollwinners album. Montgomery recorded with his brothers and various other group members, including the Wynton Kelly Trio which previously backed up Miles Davis.
John Coltrane asked Montgomery to join his band after a jam session, but Montgomery continued to lead his own band. Boss Guitar seems to refer to his status as a guitar-playing bandleader. He also made contributions to recordings by Jimmy Smith. Jazz purists relish Montgomery's recordings up through 1965, and sometimes complain that he abandoned hard-bop for pop jazz towards the end of his career, although it is arguable that he gained a wider audience for his earlier work with his soft jazz from 1965–1968. During this late period he would occasionally turn out original material alongside jazzy orchestral arrangements of pop songs. In sum, this late period earned him considerable wealth and created a platform for a new audience to hear his earlier recordings.
He didn't have very long to enjoy his commercial success, however; on June 15, 1968, while at home in Indianapolis, Indiana, U.S., he woke one morning, remarked to his wife that he "Didn't feel very well," and minutes later collapsed, dying of a heart attack within minutes. Montgomery's home town of Indianapolis has named a park in his honor. He is the grandfather of actor Anthony Montgomery.