Ishtar

If you think this looks rough, you should see the box office receipts.

Ishtar was a comedy movie about a pair of talentless and incredibly stupid lounge singers, Lyle Rogers and Chuck Clarke, who can only get booked in the Middle East, where war rages and religious fanatics claim of a prophecy involving two men who will bring down the country's brutal leader. Since the CIA has major fundings in this country's current government, they first train Chuck as a spy, while Lyle falls in line with the rebels. Then when the government of Ishtar learns that these two "smucks" might be confused with the prophets, the CIA sends the two of them out into the desert to get lost, and then try to kill Rogers and Clarke when they accidentally manage to navigate through the desert and not die. Due to all the various political conflicts brought up by these events, the United States makes a deal with the lounge singers, which involves giving the people of Ishtar more freedom and Rogers and Clarke a recording countract.

The production of Ishtar was set into motion by way of the fact that writer/director Elaine May had cowritten one Warren Beatty hit (Heaven Can Wait) and did a major rewrite on another Beatty hit (Reds), and Beatty wanted to work with her on something that she wrote and directed. May came up with an idea inspired by the Bob Hope and Bing Crosby Road To series and got another bankable, respected actor, Dustin Hoffman, to costar. A big studio, Columbia Pictures, put a lot of money into this movie. What could possibly go wrong?

This movie had a lot of production problems. Firstly, the Coca-Cola Corporation, which owned Columbia at the time, insisted that due to other business deals Coca-Cola was involved with, the movie had to be shot in the real Sahara Desert, even though it would have been cheaper to shoot it in the Southwest United States. There were high political tensions in North Africa that made the movie dangerous to shoot (there were worries that Palestinian terrorists might try to kidnap Hoffman), and Executive Meddling, combined with a conflict between producer/star Beatty and May (both strong perfectionists with differing ideas on how the film should have been shot), brought the costs up further.

The film was completed, and it was Actually Pretty Funny. New York Times film critic Vincent Canby listed it as one of the best films of the year, and multiple film directors have cited it as one of their favorite movies, including Martin Scorsese, Quentin Tarantino and Edgar Wright. Beatty and Hoffman were also happy with the final film.

However, the studio changed heads during release, and the new executive, David Puttnam (who had previously competed against Beatty for a Best Picture Academy Award with their films, Chariots of Fire and Reds, respectively), sabotaged the movie by slamming it and its actors, setting off a whirlwind of bad promotion. A majority of film critics, riled by the expense of the film, slammed it, without giving it too much of a chance, and this film was so much of a loss for Columbia that the studio was sold to Sony, who folded it into TriStar Pictures following a similar box office failure for Terry Gilliam's The Adventures of Baron Munchausen. However, despite its reputation as a "flop", Ishtar actually beat out some good competition, and could have done financially well if it had not been so expensive to produce. Still, its massive financial failure caused significant damage to its reputation.

Despite the poor reception it received at the time, Ishtar is not received nearly as badly as it once was, and even though it is one of a handful of films that are synonymous with the phrase "Box Office Bomb", most viewers find it relatively entertaining. In fact, Gary Larson apologized for a Far Side cartoon he did in which this film was the only one in Hell's Video Store, because he had only done the comic on the basis of its reputation and had not actually seen the film until it was played on an airplane, and he found himself enjoying it.

Tropes used in Ishtar include:

Actually Pretty Funny: Most viewers admit that in spite of its reputation, Ishtar actually is a funny movie.
Dueling Stars Movie
Executive Meddling: The production costs are substantially higher than they should have been, due to this. In addition to the location costs, Beatty and May had a conflict during the shoot over the way May was directing the film, and Columbia executive Fay Vincent insisted that each scene be shot twice according to how both saw each scene.
Hollywood Tone Deaf: Clarke and Rogers.
Playing Against Type: Hoffman is known for playing nerdy outcasts, and Beatty is known for playing good looking womanizers. Here, Beatty plays a shy dope who's terrible with women, and Hoffman plays the womanizing character. Many fans of the movie see this as an intentional joke, and part of the film's humor style, but May claims that it wasn't a joke, and that the actors are not playing against type because Beatty really is from the South and Hoffman really is from New York.