Ishtar (1987)

In Hollywood, Elaine May’s Middle-Eastern Cold War farce Ishtar has become synonymous with failure. The film had a notoriously catastrophic production; discord abounded, tempers flared, and friendships shattered. Production went so far over budget that Ishtar became the biggest-budget comedy in history up to that point. May found herself fighting against everyone as well as her own health. Ishtar earned only about 26% of what it cost. Critics called it every name in the book. What started as star Warren Beatty vouchsafing a career opportunity to his friend May ended in a dramatic falling-out between the two and later a breakup between Beatty and his then-girlfriend, co-star Isabelle Adjani, because of this film. May found her directing career destroyed and her Hollywood career in general reduced to a tiny trickle. Only in the last few years has the film become even possible to procure legally in America.

So infamous has its reputation become that to this day, critics use it as a standard by which they judge modern-day box office failures. For instance, Waterworld’s box office failure induced critics to derisively nickname it “Fishtar.”

Road to Morocco (1942)

In their heyday, Bing Crosby and Bob Hope teamed up to make seven Road to… films. Road to Morocco, the third one, made history as the first feature film to have characters break the fourth wall. It serves as a typical example of contemporaneous Hollywood comedies, of the chemistry common in comedy teams in the days of vaudeville, and most annoyingly, of how film portrayed Arabs at the time.