Having originally conceived it as an animation sequence in Monty Python's The Meaning of Life, Terry Gilliam convinced the rest of Monty Python to allow him to produce and direct it as a live-action piece. According to Gilliam, its rhythm, length, and style of cinematography made it a poor fit as a scene in Monty Python's The Meaning of Life, so it became "Our Short Feature Presentation" and preceded the film.
In the film, a group of elderly office clerks who work for the Permanent Assurance Company, a staid British insurance accountancy firm which has been taken over by The Very Big Corporation of America, rebel against their corporate masters when one of them is sacked. Having locked the surviving supervisors in a safe and thrown their boss out of a window on a makeshift plank, they commandeer their building and turn it into a galleon, sailing through the City of London (London's business district) and attacking The Very Big Corporation of America's skyscraper using wooden file cabinets which have become transformed into carronades. With ropes, they then swing into a board room and engage their bosses in hand-to-hand combat, vanquishing them.
After their hard-earned victory, the clerks continue to "sail the wide accountant-sea" (as they sing in their heroic sea shanty), until unceremoniously meeting their (now-animated) end by falling off the Flat Earth.
They do briefly appear within Monty Python's The Meaning of Life itself, where their raid is halted by another skyscraper "collapsing" onto the sailing Permanent Assurance Company building, with a voice-over apologizing for the temporary interruption by the supporting feature. Also, in what may be considered to be a "deleted scene" to the original short, the bosses are shown discussing the meaning of life (and the fact that people are not wearing enough hats) right before the raid.
- According to the new Monty Python's Meaning of Life DVD, it was this short that immediately won the audience in the Cannes Film Festival.
- Terry Gilliam shot this feature with a different cast and crew of the main movie (although at least four of the Monty Python members can be seen within the short). Reportedly it went quite over budget, almost double. Terry Gilliam has defended himself by saying "nobody told me to stop". Initially planned as a 5 minute sketch, it eventually expanded to half an hour. In the movie, it is edited down to 16 minutes.
- At the beginning, the building used for shooting was the Lloyd's Register (of Shipping) No.71 office in Fenchurch Street, not to be confused with the Lloyd's of London Insurance Building.
- The film's score was based on the works of Erich Wolfgang Korngold, mainly his work The Sea Hawk (1940 film).
- The Pythons have claimed that the only reason The Meaning of Life went to the Cannes Film Festival was the short, because of its stylistic nature.
- The various subsidiaries of the Very Big Corporation Of America are displayed in the corporate briefing room, as an endlessly repeating list covering all of the walls. Some of the names contain intentional in-jokes which reference other events in The Meaning of Life (such as the Live Organ Transplants scene, which immediately cuts to a scene in the briefing room where the painter is inscribing "Liver Donors Inc."). Some on the companies that can be seen on the wall are:
|The Very Big Corporation of America|
|Money Factor Printers Ltd.|
|Super Big Ltd.|
|Dawking's Mining Co.|
|Horace Mann and Yure Ltd.|
|Vast Holdings (Europe) Ltd.|
|Star Bright Merchandise Org.|
|Black and White Picture Co. Ltd.|
|D.Odgey Enterprises Ltd.|
|Consolidated Steel Co.|
|Acme Construction Company|
|Universal Amalgamations Ltd.|
|Rubber Goods Incorporated|
|The All Enveloping Co. Ltd.|
|Walker, Walker and Jones Bros.|
|Better Plastics Corps.|
|Space Propulsion Lab|
|Lange and Sons (International)|
|R. Devious Inc.|
|Phil Thevich Consortium|
|X. Tortion World Wide Ltd.|
|Mirage Land Co.|
|E. Normons and Sons|
|Micro Computer Inc.|
|Payne, Bickers and Dogood Ltd.|
|World Wide Wine Corp.|
|A. Maze and Lee Huge|
|Dickinson Kincain Association|
|D. Crepid Holdings|
|Interstellar Travel Corp.|
|Wakefeld and Daughter|
|Fastness and Vast Co. Ltd|
|Arctic Geo. Lab. Co.|
|R. J. McArthur Parks Ltd.|
|Stn. Pendons Ltd.|
|V. Rich and Son|
|Liver Donors Inc.|
|Moonscape Products Ltd.|
|Data Travel and Experiments|
|O. Verpaid Associates Ltd.|
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