In 1984, British filmmaker and artist Derek Jarman was visiting Moscow, along with Sally Potter and Peter Wollen, at the invitation of the Soviet Union. Jarman was allowed to show his feature film The Tempest there in exchange for a short film that would report on their travels. The trip included visits to the historic Bolshoi theatre, the State Circus, and the flat of filmmaker Sergei Eisenstein. Jarman later added footage shot in London.

Imagining October explores art and politics in the Cold War's final years, connecting pre-Perestroika Russia and Thatcher's United Kingdom. The title refers to the 1917 Bolshevik revolution and Eisenstein's 1928 propaganda film October: Ten Days That Shook the World.

Jarman died of AIDS in 1994. Imagining October is emblematic of much of his cinematic work: queer, politically tinged, activist, and dreamy.