- All-Star Cast: Graham Chapman in the title role, and a colorful lineup of comic and character actors supporting him: in alphabetical order, Peter Boyle, Cheech & Chong, John Cleese, Peter Cook, Marty Feldman, Michael Hordern, Eric Idle, Madeline Kahn, Kenneth Mars, James Mason, Spike Milligan, Beryl Reid, and Susannah York. And an unbilled cameo by David Bowie! It definitely qualifies.
- Awesome, Dear Boy: David Bowie agreed to be in the film purely to work with the Pythons.
- California Doubling: A whole section of the harbor at the Mexican resort town of Acapulco was made over to look like the English sea village of Portsmouth in the 17th Century.
- Career Killer: Martin Hewitt never recovered from being the lead of the film, after having a promising start to his career.
- Channel Hop: Graham Chapman unsuccessfully tried to get the film made at Hand Made Films. It was later picked up by Orion Pictures.
- Creator Backlash: John Cleese and Eric Idle have called this one of the worst films ever made. Cleese did it purely as a favour to Graham Chapman, while Idle later said "the best times can be on the worst movies and vice versa, e.g., Yellowbeard, which I wouldn't have missed for the world".
- Dawson Casting: Dan is supposed to be 15, but is played by a 25 year old Martin Hewitt.
- Died During Production: Marty Feldman, who played Gilbert, died of a heart attack before filming was to be wrapped. A stunt double was brought in to film his death scene.
- Executive Meddling: Not only was the original script rewritten, Graham Chapman was not allowed to assist with the editing, and his editing comments on the first cut were ignored. His comments included shortening the credits so that audience expectation was not too far raised, and making the jokes less obvious.
- Prop Recycling: Three ships in the film were portrayed by Metro-Goldwyn-Mayer's Bounty II, built for the 1962 version of Mutiny on the Bounty.
- Saved from Development Hell: The picture spent a very long time in development hell taking a considerable amount of time to secure financing.
- Uncredited Role: David Bowie as the shark.
- What Could Have Been:
- Adam Ant was originally cast as Dan but quit after losing patience with delays in production. Sting was then approached and wanted the role, but the producers insisted on an American actor. Martin Hewitt was finally cast. Hollywood executives thought the picture was becoming too English and mandated an American actor be cast and in the end this was Martin Hewitt who once said, "Sting should have had my part. For crying out loud, I would have hired Sting over me any day."
- Graham Chapman devised the project with his friend Keith Moon, who would have played the lead role were it not for his death. And they wanted mutual friend Sam Peckinpah directing.
- Terry Jones turned down the role of Dr. Gilpin and Michael Palin turned down the role of Dan, thus denying us a (nearly) full Monty Python reunion.
- Harry Nilsson was originally asked to compose the soundtrack, including a song for the main cast to sing.
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