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As his alter ego Maxwell DeMille, Sheff has hosted and directed vintage-themed theatrical productions at the historic Orpheum Theatre in Los Angeles, drawing audiences of over 2,000.

His first feature, Sinister Flesh (1976), was a satirical black-and-white horror film that earned praise among genre and sci-fi fans for its homage to B-movie horror classics.

Stanley Sheff is the only filmmaker ever to share an uncredited co-directing credit with Orson Welles (under the pseudonym G.O. Spelvin), having collaborated, edited, and acted in The Orson Welles Show (1979), Welles' final completed work.

Created and co-hosted the KROQ-FM cult comedy radio show The Young Marquis and Stanley, blending Golden Age Hollywood satire with surrealist humor. Although it aired Sunday at midnight, the show received massive amounts of fan mail.

Directed Lobster Man from Mars (1989) - a title suggested by Orson Welles - a sci-fi comedy homage that starred Tony Curtis and premiered at the Sundance Film Festival. The film has since developed a cult following.

Edited Motown Returns to the Apollo (1985), a star-studded NBC television special that won an Emmy Award. The broadcast was edited in a single 57-hour session to meet an air date deadline.

A longtime advocate for merging classical filmmaking styles with modern technologies, Sheff is developing a true crime dramatic series set in the 1920s integrating AI-assisted workflows and virtual LED stage production.