He became known for his extremely prolific output in a wide range of styles and media, superfiction, as well as his provocative, jocular and hard-drinking public persona.

[1] Leaving Berlin, originally for a long visit to Paris, Kippenberger spent the early 1980s as an active member of the Cologne art scene.

The Vienna gallerist Peter Pakesch thinks Kippenberger did an enormous amount for the Hetzler Gallery's success in his double role "as clown and strategist... Max without Martin's strategy would have been unimaginable in the early years."

[2] He stayed in Sankt Georgen im Schwarzwald as a guest of the Grässlin family of art collectors from 1980 to 1981, and later on and off from 1991 to 1994, in order to work but also to recover from his excessive life.

[8] Kippenberger’s refusal to adopt a specific style and medium in which to disseminate his images resulted in an extremely prolific and varied oeuvre which includes an amalgam of sculpture, paintings, works on paper, photographs, installations, prints and ephemera.

[11] Kippenberger also felt that he was working in the face of a 'perceived death of painting' and his art reflects his struggle with the concept that, at the turn of the millennium, it was impossible to produce anything original or authentic.

Restaging a well-known photograph by David Douglas Duncan of Picasso standing in a 'puffed-up' state of undress on the steps of Château of Vauvenargues in 1962 Kippenberger was parodying his famous antecedent, playfully subverting the machismo associated with the genre of self-portraiture.

First adopted as a motif in his 1988 series of self-portraits undertaken in Carmona, Spain, Kippenberger depicted himself with white briefs pulled up high over his exaggerated belly, as he turned to examine himself in a mirror.

The installation consists of a diverse assortment of objects and furniture, assembled to suggest a playing field for conducting mass interviews.

[23][24] Originally undertaken as ad hoc preparatory diagrams for the three-dimensional Peter sculptures, he later used the myriad letterheads of innumerable hotels to capture other subjects and inspirations.

[28] In 2011, Kippenberger's When It Starts Dripping From the Ceiling was accidentally destroyed by a janitor in a Dortmund museum who believed she was cleaning stains off of the work.

[29] In 1985, Kippenberger exhibited "Buying America and Selling El Salvador" at Metro Pictures Ltd in New York, a large installation comprising numerous sculptural works.

[31] Kippenberger collected and commissioned work by many of his peers: some of his exhibition posters were designed by such prominent artists as Jeff Koons, Christopher Wool, Rosemarie Trockel and Mike Kelley.

[33][34] On 12 May 2014, a Kippenberger’s untitled self-portrait, from 1988, restaging a photograph of the 81-year-old Picasso in his white underwear taken by David Douglas Duncan, fetched $18,645,000, at Christie's New York.

In 2008, during an exhibition at the Museion in Bozen, Italy,[40] a sculpture by Kippenberger depicting a toad being crucified called Zuerst die Füsse ("First the Feet") was condemned by Pope Benedict as blasphemous, despite the museum's explanation that it was a "self-portrait illustrating human angst".