The Crimson Permanent Assurance is a short film that appears before the 1983 Monty Python movie The Meaning of Life.

Originally conceived as an animated sequence in 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 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 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 pirate ship, sailing within London's business district and attacking The Very Big Corporation of America's skyscraper using wooden file cabinets which have become either technologically or magically 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 accountancy" (as they sing in their heroic sea shanty), until unceremoniously meeting their (now-animated) end by falling off the edge of the world.

They do briefly appear within The Meaning of Life itself, where their raid is halted by another skyscraper "collapsing" onto the sailing Permanent Assurance Company building. Also, in what may be considered to be a "deleted scene" to the original short, the bosses are discussing the meaning of life (and the fact that people are not wearing enough hats) right before the raid.

According to the new Meaning of Life DVD, it was this short that immediately won the audience in the Cannes Film Festival.