In 1989, Stillman made his first feature, "Metropolitan", a low-budgeted yet highly polished portrait of Manhattan's east-side debutante set. Deftly observed and gently satirical, the film was a hit on the festival circuit, earned Stillman a Best Original Screenplay Academy Award nomination, and grossed an impressive $3 million. It also attracted the attention of Hollywood in the form of Castle Rock Pictures. The top brass expressed interest in funding "Barcelona" (1994) while giving the neophyte filmmaker creative control and final cut. Castle Rock provided $4 million for "Barcelona", another droll, dialogue-driven character study. Inspired in part by Stillman's surprise over his Spanish friends' hostile reaction to "An Officer and A Gentleman" (1982), the film detailed the personal and political misadventures of a mismatched pair of American cousins in post-Franco Spain.