As labor strikes break out throughout the country, New York City is alive with a burgeoning cultural revolution. Nelson Rockefeller (John Cusack) commissions Mexican artist Diego Rivera (Ruben Blades) to paint the lobby of Rockefeller Center while Italian propagandist Margherita Sarfatti (Susan Sarandon) gives Da Vincis to millionaires who help fund the Mussolini war effort. An alcoholic ventriloquist (Bill Murray) tries to rid his vaudeville troupe of communists while a 22-year-old Orson Welles (Angus MacFadyen) directs his Federal Theater group in an infamous stage production of The Cradle Will Rock, which is closed down on the eve of its opening by soldiers of the US government.

Based on true events, The Cradle Will Rock re-lives an exciting and dangerous time in American history when individual courage stood in the face of censorship and artists risked their livelihood by performing in shows and painting their canvases.