In 1980, he first arrived in Leningrad. In 1981, after meeting Sergey Kuryokhin, he became a member of his first "KreziMusic Orchestra", later known as "Pop Mechanics". At the same time, he participated in the groups "Kino", "Aquarium", and "Sounds of Mu". In 1982, he joined Timur Novikov’s group "New Artists", with which he first exhibited in 1983.

In the 1990s, he gained recognition on the global art scene. His solo exhibitions took place in London, New York, Paris, Vienna, and Zurich. Several exhibitions were also held in Germany and Finland.

In Russia, the most significant exhibitions were: in 1993 — "Africa" (State Russian Museum, St. Petersburg), in 2001 — "The Dream of Jacobson (Big Rebus)" (Central House of Artists, Moscow), in 2005 — "The Unconscious: Don’t Trust Your Eyes" (State Tretyakov Gallery).

In 1999, he represented Russia at the 48th Venice Biennale (project MIR: Made in 20th century).

His works are held in museum collections in various countries and in private collections worldwide. Works from the series "Rebus", created on pieces of glass-epoxy, can be seen in New York, Paris, Vienna, and Brussels.

At the end of 2007, Sergey Bugayev founded the Free Arts Fund "Institute of the New Man", which supports young artists, promotes, and educates in the field of contemporary art.