Shipp moved to New York in 1984 and has been very active since the early 1990s, appearing on dozens of albums as a leader, sideman, or producer. Shipp, before making a living playing music, worked in a bookshop as an assistant manager. He got fired, he threw some books at his boss, and he decided he wouldn't look for a day job anymore. He was initially most active in free jazz but has since branched out, notably exploring music that touches on contemporary classical, hip hop, and electronica. At the beginning of his career Shipp was stylistically 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 and recognizable style"; and Larry Blumenfeld in Jazziz Magazine referring to Shipp as "stunning in originality." Jazziz Magazine also referred to Shipp's CD 4D as "further proof of his idiosyncratic genius." Shipp was a longtime member of saxophonist David S. Ware's quartet with bassist William Parker and alternating drummers. He has recorded or performed with many other musicians, including High Priest and Beans of Antipop Consortium, Michael Bisio, Guillermo E. Brown, Daniel Carter, Whit Dickey, Newman Taylor Baker, DJ Spooky, El-P, Susie Ibarra, Mat Maneri, Roscoe Mitchell, Joe Morris, Ivo Perelman, and Mat Walerian. In February 2011, Shipp released a double-disc album entitled Art of the Improviser. This release is "testament to Shipp's achievements, yet it is also a continuation of the discovery in his developmental musical language." The Chicago Tribune called the project "monumental" and "galvanic as ever." Shipp has been continuously improving his repertoire from touring the world, writing new compositions and, since 2011, has been collaborating with Barbara Januszkiewicz. Together they are exploring new territory through an avant-garde film called The Composer with Matthew Shipp / Barb Januszkiewicz. On September 24, 2013, Thirsty Ear Records released a solo piano CD by Shipp called Piano Sutras. Will Layman, writing for PopMatters, described it as:
the kind of record we talk about and play for each other decades later... This is 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.
