[6] He opted instead to live with his parents and focus on practicing, though he frequently traveled to Philadelphia to pick up gigs as a cocktail pianist and to study with Dennis Sandole, who Shipp has cited as playing an important role in his development.

[6] He later spent a year at the New England Conservatory of Music, where he studied with saxophonist and composer Joe Maneri, but again dropped out without completing a degree.

[8])He was initially most active in free jazz but has since branched out, particularly exploring music that touches on contemporary classical, hip hop, and electronica.

[9] Earlier in his career Shipp was compared to some of his predecessors in the jazz piano pantheon, but has since been recognized as a complete stylistic innovator on the piano, with AllMusic referring to his "unique, instantly recognizable style",[10] and Larry Blumenfeld in Jazziz magazine referring to Shipp as "stunning in originality" and to his album 4D as "further proof of his idiosyncratic genius".

[6] As a member of Ware's quartet, Shipp recorded albums for Homestead (Cryptology and DAO), Thirsty Ear (Threads, Live in the World, BalladWare), AUM Fidelity (the label's first release, Wisdom of Uncertainty, as well as Corridors & Parallels, Freedom Suite, and Renunciation), Silkheart (Great Bliss, Vol.

[14] After Ware's death, Shipp wrote, "Some have compared our unit to the classic Coltrane quartet, but the members of our group all brought something to the table that only someone playing now could bring—resulting in a gestalt that is of its time and does not look back.

The New York Times has noted Shipp's curatorial work for Thirsty Ear Records as "one of the label's chief consultants and most prolific artists".

[19] Thirsty Ear also released Shipp's 2013 solo record Piano Sutras, which PopMatters described as "the kind of record we talk about and play for each other decades later ... music that frames up a whole history: of an artist, of listeners, of the artists who formed the history of the art form, of the culture and time that allowed this art to flourish".

"[26] In 2022 a duo album by Shipp and Ivo Perelman, Fruition, was released by ESP, with NPR's Nate Chinen stating in his review, "The freeform alchemy between Brazilian saxophonist Ivo Perelman and American pianist Matthew Shipp is by now a proven fact: rarely do two musicians achieve a higher flow state in real time.