He played with leading bebop musicians and formed his own small bands, which soon displayed some of his early interests – contrapuntal interaction of instruments, harmonic flexibility, and rhythmic complexity.

His educational role over three decades meant that he exerted an influence on jazz through his students, including saxophonists Lee Konitz and Warne Marsh.

Some describe his playing as cold and suggest that his innovations had little impact; others state that he was a bridge between bebop and later, freer forms of jazz, and assert that he is less appreciated than he should be because commentators found him hard to categorize and because he chose not to commercialize.

[9] He first received press coverage for his piano playing in early 1944, appearing in Metronome's summary of music in Chicago from that year, and then in Down Beat from 1945.

[10] He recorded with some musicians from Woody Herman's band in 1945; Tristano's playing on these tracks "is characterized by his extended harmonies, fast single-line runs, and block chords.

[14] As a preliminary step to moving there, he stayed in Freeport, Long Island,[15] where he played in a restaurant with Arnold Fishkind (bass) and Billy Bauer (guitar).

[20] They played together in bands that included bebop musicians Dizzy Gillespie and Max Roach later that year for radio broadcasts.

[17][26] The sextet recorded original compositions, including his "Wow" and "Crosscurrent", that were based on familiar harmonies; reviewers commented on the linearity of the playing and its departure from bebop.

[32] Numerous other musicians of the time, however, thought Tristano's music too progressive and emotionally cold, and predicted that it would not be popular with the public.

[33] The sextet struggled to find enough work, but did play at Birdland's opening night "A Journey Through Jazz", a subsequent five-week engagement at that club, and at various other venues in the north-east of the US late in 1949.

[34] They performed free pieces in these concerts, as well as Bach fugues,[35] but found it difficult over time to continue to play with the freedom that they had initially felt.

[37] In the same year, the location for Tristano's lessons shifted from his home in Flushing, Queens to a Manhattan loft property,[38] part of which he had converted into a recording studio.

[42] The two tracks were from a trio session with bassist Peter Ind and drummer Roy Haynes,[43][44] and contained overdubbed second piano parts added later by Tristano.

[50] It was a musical portrayal of Edgar Allan Poe's story of the same title, and was an improvised solo piano piece that used multitracking and had no preconceived harmonic structure, being based instead on the development of motifs.

[54] The eponymous album included solo and trio tracks that contained further experiments with multitracking ("Requiem" and "Turkish Mambo")[17] and altered tape-speed ("Line Up" and "East 32nd").

[59] For "Line Up" and "East 32nd", Tristano's "use of chromatic harmony ... secures him a position of a pioneer in expanding the harmonic vocabulary of jazz improvisation", in biographer Eunmi Shim's words.

[68] The tracks contain left-hand bass lines that provide structure to each performance as well as counterpoint for the right-hand playing;[69] block chords, unclear harmonies and contrasting rhythms also appear.

[73] In 1964 the pianist reformed his quintet with Konitz and Marsh for a two-month engagement at the Half Note and performances at the Coq D'Or in Toronto.

[78] 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.

"[84] 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.

[86] 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.

[90] 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.

[95] Bebopper Bud Powell also affected Tristano's playing and teaching, as he admired the younger pianist's articulation and expression.

[100] 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.

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.

Typically, his solos consisted of extraordinarily long, angular strings of almost even quavers provided with subtle rhythmic deviations and abrasive polytonal effects.

[78] Fellow piano player Ethan Iverson asserted that, "As a pianist, Tristano was in the top tier of technical accomplishment.

"[101] Tristano "had seemingly small but extremely flexible hands, which could expand to a phenomenal degree", allowing him to reach large intervals.

[116] Max Harrison indicated that the pianist had limited influence outside his own group of affiliated musicians;[117] Robert Palmer, who pointed out that only one of Tristano's albums was in print at the time of his death,[83] suggested that he was pivotal in the change from 1940s modern jazz to the freer styles of subsequent decades; and Thomas Albright similarly believed that his improvising prepared and developed new ground in the history of the music.

"[125] Shim suggested that the common under-appreciation of Tristano is attributable in part to his style being unusual and too difficult for jazz commentators to categorize.