Coming to prominence with the band of Count Basie, Young is remembered as one of the finest, most influential players on his instrument, playing with a cool tone and sophisticated harmonies. He also became a jazz legend, inventing or popularizing much of the hipster ethos which came to be associated with the music.
Young left the Basie band to replace Hawkins in Fletcher Henderson's orchestra, but, feeling pressure to play more like Hawkins, he soon left Henderson to join the Andy Kirk band (for six months) and, eventually, return to Basie.
While with Basie he made small-group recordings for Milt Gabler's Commodore Records, The Kansas City Sessions, which although they were in fact recorded in New York (in 1938, with a reunion in 1944), are named after the group, the Kansas City Seven, and comprised Buck Clayton, Dicky Wells, Basie, Young, Freddie Green, Rodney Richardson and Jo Jones. Young played clarinet as well as tenor on these sessions; he was a master of the clarinet, and there too, his style was entirely his own. As well as the Kansas City Sessions his clarinet work from 1938-39 is documented on recordings with Basie, Billie Holiday, Basie small groups, and the obscure organist Glenn Hardman. His clarinet was stolen in 1939, and he abandoned the instrument until about 1957, when Norman Granz gave him one and urged him to play it (with far different results at that stage in Young's life - see below).
Young was viewed as an eccentric by those he chose to exclude from his circle (those he did not trust). He did so by creating his own language that his friends could understand, that might baffle outsiders. Those on the outside viewed it as a rococo and often inscrutable personal slang, famously referring to a narcotics detective or policeman as a "Bob Crosby" (referring to Bob and Bing Crosby if multiple police officers were present), a rehearsal as a "molly trolley", and an instrumentalist's keys or fingers as his "people". He dressed distinctively, especially in his trademark pork pie hat. When he played saxophone, particularly in his younger days, he would sometimes hold the horn off to the right side at a near-horizontal angle, like a flute. Joop Visser believes that it was Lester's residence in the stuffy Reno Club with the Count Basie Band that caused this idiosyncrasy, as by holding it that way it was the only way Lester could keep his tenor sax from knocking into someone else's instrument. He is considered by many to be an early hipster, predating Slim Gaillard and Dizzy Gillespie.
During this period, Young accompanied Billie Holiday on a couple of great studio sessions in 1940 and 1941, and also made a small set of brilliant recordings with Nat "King" Cole (their first of several collaborations) in June 1942. It should be noted that his studio recordings are relatively sparse during the 1942 to 1943 period, largely due to the American Federation of Musicians' recording ban of that period that reflected the war effort.
In December 1943, Young returned to the Basie fold for what ended up being a 10-month stint, cut short by his army induction (see below). Recordings made during this and subsequent periods suggest Young was beginning to make much greater use of a plastic reed, which tended to give his playing a somewhat heavier, breathier tone (although still quite smooth compared to that of many other players). While he certainly never abandoned the wooden reed, he did utilize the plastic reed a significant share of the time from 1943 until the end of his life. Another cause for the thickening of his tone around this time was a change in saxophone mouthpiece from a metal Otto Link to an ebonite Brilhart. In August 1944, Young appeared alongside drummer Jo Jones, trumpeter Harry "Sweets" Edison, and fellow tenor saxophonist Illinois Jacquet in Gjon Mili's film short Jammin' the Blues.
Some jazz historians have argued that Young's playing power declined in the years following his traumatic army experience, though critics such as Scott Yanow disagree with this entirely. Recordings show that his playing began to change before he was drafted. Some argue that Young's playing had an increasingly emotional slant to it, and the post-war period featured some of his greatest renditions of ballads.
While the quality and consistency of his playing arguably ebbed gradually in the latter half of the 1940s and into the early 1950s, he did give some brilliant performances during this stretch. Particularly noteworthy are his performances with JATP in 1946, 1949, and 1950—his solo on "Lester Leaps In" at the 1949 JATP concert at Carnegie Hall stands as perhaps one of the greatest solos by any jazz musician ever. The line-up for that concert included Charlie Parker and Roy Eldridge.
He emerged from this treatment considerably improved, as evidenced by his January 1956 Granz-produced sessions with pianist Teddy Wilson (who had led the Billie Holiday recordings with Young in the 1930s). Another success that year was the Jazz Giants '56 session with Roy Eldridge, trombonist Vic Dickenson and other swing-era artists. In all 1956 was a relatively good year for Lester Young, including a tour of Europe with Miles Davis and the Modern Jazz Quartet and a successful stint at Olivia's Patio Lounge in Washington DC.
Throughout the 1940s and 50s Young had sat in on Count Basie Orchestra gigs from time to time. The best-known of these is their July 1957 appearance at the Newport Jazz Festival, the line-up including many of Lester's old buddies: Jo Jones, Roy Eldridge, Illinois Jacquet and Jimmy Rushing. His playing was in better shape than usual at this time, and he even managed to produce some of the old, smooth toned flow of the 1930s. Among other tunes he played a moving "Polkadots and Moonbeams", which was a favorite of his at that time.
Lester Young made his final studio recordings and live performances in Paris in March 1959 with drummer Kenny Clarke at the tail end of an abbreviated European tour during which he ate next to nothing and virtually drank himself to death. He died in the early morning hours of March 15, 1959, only hours after arriving back in New York, at the age of 49. According to renowned jazz critic Leonard Feather, who rode with Holiday in a taxi to Young's funeral, she told Feather on the ride over, "I'll be the next one to go." She died only four months later at the age of 44.
Young's playing style influenced many other tenor saxophonists. Perhaps the most famous and successful of these were Stan Getz and Dexter Gordon, but he also influenced many in the cool movement such as Zoot Sims, Al Cohn, and Gerry Mulligan. Paul Quinichette modeled his style so closely on Young's that he was sometimes referred to as the 'Vice Prez'. Sonny Stitt began to incorporate elements from Lester Young's approach when he made the transition to tenor saxophone. Lester Young also had a direct influence on young Charlie Parker ("Bird"), and thus the entire be-bop movement. Indeed, recordings of Parker on tenor sax are similar in style to that of Young. Lesser known saxophonists, such as Warne Marsh, were strongly influenced by Young.
Don Byron recorded the album Ivey-Divey in gratitude of what he learned from studying Lester Young's work, modeled after a 1956 trio date with Buddy Rich and Nat King Cole. "Ivey-Divey" was one of Lester Young's common eccentric phrases.
In the 1986 film Round Midnight, the fictional main character Dale Turner, played by Dexter Gordon, was partly based on Young - incorporating flashback references to his army experiences, and loosely depicting his time in Paris and his return to New York just before his death.
Acid Jazz/boogaloo band the Greyboy Allstars song "Tenor Man" is a tribute to Young. On their 1999 album "Live", saxophonist Karl Denson introduces the song by saying, "now some folks may have told you that Lester Young is out of style, but we're here to tell you that the Prez is happenin' right now."
Peter Straub's short story collection Magic Terror (2000) contains a story called "Pork Pie Hat", a fictional account of the life of Lester Young. Straub was inspired by Young's appearance on the 1957 CBS-TV show, The Sound of Jazz, which he watched repeatedly, wondering how such a genius could have ended up such a human wreck.