Bennink attended art school in the 1960s, and is also a successful visual artist in several media, often constructing sculpture from found objects, which may include broken drum heads and sticks. He has designed the covers for many LPs and CDs on which he appears. Bennink is represented by Amsterdam's Galerie Espace, and has been the subject of several one-man shows, including one at the Gemeente Museum in the Hague in 1995.
In 1966, Bennink played the US's Newport Jazz Festival with the Mengelberg quartet. From the late 1960s through the '70s Bennink collaborated frequently with Danish, German, English and Belgian musicians, notably saxophonists John Tchicai and Peter Brötzmann, guitarist Derek Bailey and pianist Fred van Hove. Bennink, Brötzmann and van Hove had a longstanding trio well documented on FMP Records. There Bennink also showcased his talents on clarinet, trombone, soprano saxophone and many other instruments, also featured in a series of solo albums he began in 1971.
Bennink's many recordings from the 1980s include sessions with Mengelberg's ICP Orchestra (where he remains), South African bassist Harry Miller, soprano saxophonist Steve Lacy, trombonists Roswell Rudd and George Lewis, and big-bandleaders Sean Bergin and Andy Sheppard.
From 1988 to '98 Bennink's main vehicle was Clusone 3, with saxophonist and clarinetist Michael Moore and cellist Ernst Reijseger, a band noted for its free-wheeling mix of swinging jazz standards, wide-open improvising, and tender ballads. Clusone played Europe and North America, West Africa, China, Vietnam and Australia, and recorded five CDs for Gramavision, hat Art and Ramboy.
These days he is frequently heard with tenor saxophonist Tobias Delius's quartet and in a trio with pianist/keyboardist Cor Fuhler and bassist Wilbert de Joode, and he still collaborates occasionally with jazz luminaries such as Johnny Griffin, Von Freeman and Ray Anderson.
A conspicuous feature of Bennink's musical life since the 1960s is the spontaneous duo concert with musicians of many nationalities and musical inclinations; in the '90s he recorded in duo with among others pianists Mengelberg, Irene Schweizer and Myra Melford, guitarist Eugene Chadbourne, trumpeter Dave Douglas and tenor saxophonist Ellery Eskelin.