Murakami was dissatisfied with the state of contemporary art in Japan, believing it to be "a deep appropriation of Western trends." Thus, much of his early work was done in the spirit of social criticism and satire. On an article naming and explaining all of Murakami's pieces lies the infamous My Lonesome Cowboy, a companion to his earlier Hiropon. The sculpture is that of a naked anime character with blond spiky hair with a spiral trail of semen circling him. This piece is Murakami's most expensive piece to date selling for $13,500,000 at Sothbye's New York auction in 2008. Efforts from this period include performance art (Osaka Mixer Project, 1992), parodies of the "message" art popular in Japan in the early '90s, (Dobozite Dobozite Oshamanbe, 1993), and conceptual works (e.g. Randoseru Project, 1991). He also began developing his own pop icon, "Mr. DOB," which would later develop into a form of self-portraiture, the first of several endlessly morphing and recurring motifs seen throughout his work. Though he garnered attention, many of his early pieces were not initially well received in Japan.
In 2008, Murakami was named one of Time magazine's "100 Most Influential People", the only visual artist included.
In 2008, Kaikai Kiki converted the basement space beneath its Tokyo office into an art gallery. Kaikai Kiki Gallery has held exhibitions not only for the artists under its management but also international names such as Mark Grotjahn and Friedrich Kunath. All exhibitions are curated by Murakami.