Tristano was born in Chicago on March 19, 1919. His mother, Rose Tristano (nee Malano), was also born in Chicago. His father, Michael Joseph Tristano, was born in Italy and moved to the United States as a child. Lennie was the second of four brothers.

Tristano's second album for Atlantic was recorded in 1961 and released the following year. The New Tristano, as was stressed on the album cover, consisted entirely of piano solos and no overdubbing or tape-speed manipulation was employed. The tracks contain left-hand bass lines that provide structure to each performance as well as counterpoint for the right-hand playing; block chords, unclear harmonies and contrasting rhythms also appear. Other solo piano recordings that Tristano made in 1961 were not released until the 1970s. Tristano and his wife formally divorced in 1962. Their son, Steve, who was born in 1952, met his father only once after their initial 1956 separation. Tristano married again in the early 1960s. His second wife was Carol Miller, one of his students. They had a son, Bud, and two daughters, Tania and Carol. The couple divorced in 1964, and Tristano later lost a custody battle with his ex-wife over the children. In 1964 the pianist reformed his quintet with Konitz and Marsh for a two-month engagement at the Half Note and more performances in Canada. The quartet, missing Konitz, played in Toronto again in the following year. Tristano played on occasion at the Half Note Club until the mid-1960s, and toured Europe in 1965. His European tour was mainly as a solo pianist, and the playing was in the style of his The New Tristano recordings. He performed with Ind and others in concerts in the UK in 1968; they were well received, and Tristano returned the following year. His last public performance in the US was in 1968. Tristano declined offers to perform in the 1970s; he explained that he did not like to travel, and that the requirement for a career-minded musician to play concerts was not something that he wanted to follow. He continued teaching, and helped to organize concerts for some of his students. Another album, Descent into the Maelstrom, was released in the 1970s; it consisted of recordings made between 1951 and 1966. Tristano had a series of illnesses in the 1970s, including eye pain and emphysema (he smoked for most of his life). On November 18, 1978 he died of a heart attack at home in Jamaica, New York. In Ind's view, Tristano "was always so gentle, so charming and so quietly spoken that his directness could be unnerving." This directness was noted by others, including bassist Chubby Jackson, who commented that Tristano had almost no tact and would not worry about being rude or making others feel incompetent. Some of his students described Tristano as domineering, but others indicated that this impression came from his demanding discipline in training and attitude to music. Writer Barry Ulanov commented in 1946 that Tristano "was not content merely to feel something, [...] he had to explore ideas, to experience them, to think them through carefully, thoroughly, logically until he could fully grasp them and then hold on to them." Tristano criticized the free jazz that began in the 1960s for its lack of musical logic as well as its expression of negative emotions. "If you feel angry with somebody you hit him on the nose - not try to play angry music", he commented; "Express all that is positive. Beauty is a positive thing." He expanded on this by distinguishing emotion from feeling, and suggested that playing a particular emotion was egotistical and lacking in feeling. Tristano also complained about the commercialization of jazz and what he perceived to be the requirement to abandon the artistic part of playing in order to earn a living from performing. Later commentators have suggested that these complaints ignored the freedom that he was given by Atlantic and blamed others for what in many cases were the outcomes of his own career decisions. Saxophonists Parker and Lester Young were important influences on Tristano's development. Another major figure was pianist Art Tatum: Tristano practiced solo Tatum pieces early in his career, before gradually moving away from this influence in search of his own style. Bebopper Bud Powell also affected Tristano's playing and teaching, as he admired the younger pianist's articulation and expression. Tristano's advanced grasp of harmony pushed his music beyond the complexities of the contemporary bebop movement: from his early recordings, he sought to develop the use of harmonies that were unusual for that period. His playing has been labeled "cool jazz", but this fails to capture the range of his playing. Biographer Eunmi Shim summarized the changes in Tristano's playing during his career: The trio recordings of 1946 show a novel approach in the linear interaction between piano and guitar, resulting in counterpoint, polyrhythm, and superimposed harmonies. The sextet recordings of 1949 are notable for coherent ensemble playing and soloing, and the free group improvisations based on spontaneous group interactions and the contrapuntal principle. In the 1950s Tristano employed an advanced concept in jazz improvisation called side-slipping, or outside playing, which creates a form of temporary bitonality when chromatic harmony is superimposed over the standard harmonic progressions. Tristano intensified his use of counterpoint, polyrhythm, and chromaticism in the 1960s[.] Grove Music commented on some aspects of Tristano's style that were different from most modern jazz: "Rather than the irregular accents of bop, Tristano preferred an even rhythmic background against which to concentrate on line and focus his complex changes of time signature. Typically, his solos consisted of extraordinarily long, angular strings of almost even quavers provided with subtle rhythmic deviations and abrasive polytonal effects. He was particularly adept in his use of different levels of double time and was a master of the block-chord style". Fellow piano player Ethan Iverson asserted that, "As a pianist, Tristano was in the top tier of technical accomplishment. He was born a prodigy and worked tirelessly to get better." Tristano "had seemingly small but extremely flexible hands, which could expand to a phenomenal degree", allowing him to reach large intervals.

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Another major figure was pianist Art Tatum: Tristano practiced solo Tatum pieces early in his career,