Monty Python’s Flying Circus is a touchstone moment in the history of television comedy. From 1969 to 1974, Circus was broadcast by the BBC, and featured sketches, written and performed by the troupe (consisting of John Cleese, Eric Idle, Michael Palin, Terry Jones, and Graham Chapman), that pushed boundaries and peculiar, unique animated bits from Terry Gilliam. Monty Python turned their absurd style of comedy to the film world as well, with five true Monty Python productions between 1971 and 1983 (1982's The Secret Policeman's Other Ball doesn't count, despite including members of the group). How take a look back at these hilarious films and see how they rank against one another.

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5. Monty Python’s The Meaning of Life (1983)

monty python's the meaning of life
Image via Universal Pictures

The final Monty Python film involving the entire troupe is also the weakest of the lot, a blackly humorous venture full of sketches chronicling birth to death. The Meaning of Life simply doesn't have anything that keeps it in the public eye. There are remarkably few quips that Python fans quote ad nauseam, with "it's only wafer thin" that immediately comes to mind. The Penis Song and Every Sperm is Sacred are the only two songs with any legs, and the only sketch that most people can remember from the film is the cringe-worthy Mr. Creosote, about a ridiculously obese man who vomits everywhere and eventually blows up. Even for Python, it's out there.

4. Monty Python Live at the Hollywood Bowl (1982)

Monty Python Live at the hollywood bowl
Image via Columbia Pictures

A concert film recorded at the renowned Hollywood Bowl, hence the title. The Python’s perform sketches and songs in front of a live audience, a greatest hits, if you will. Full marks to the group for successfully transitioning their work for the stage. Highlights include The Argument Clinic, The Travel Agent Sketch, The Lumberjack Song, Bruces/Philosopher Song, and John Cleese entering the audience as a vendor, shouting "Albatross!" Bowl would lay the groundwork for Broadway hit Monty Python's Spamalot, proving there was an appetite for Python on stage.

3. And Now for Something Completely Different (1971)

and now for something completely diffent monty python
Image via Columbia-Warner Distributors

And Now For Something Completely Different consists of sketches from the first two seasons of Circus, all recreated specifically for the film. It's the perfect introduction of Monty Python to the uninitiated, a selection that covers the whole scope of their output, from the thinking man's The Funniest Joke in the World to the outright silliness of How Not To Be Seen. The sketches largely benefit from the recreations for the big screen, adding a quality unavailable (at the time) on television. Additionally, the format allows for an easier flow between sketches, such as the The Dead Parrot sketch moving into The Lumberjack Song, a more natural sequence.

2. Monty Python’s Life of Brian (1979)

Graham Chapman as Brian in Monty Python's Life of Brian
Image via Cinema International Corporation

How does one make a film that skewers Christianity without skewering Jesus? Monty Python's Life of Brian does exactly that. Famously renowned for specifically not targeting Jesus, Brian instead focuses on the tale of Brian of Nazareth (Graham Chapman), whose life runs concurrently with Jesus'. Through a series of events, Brian becomes heralded as a prophet, only to be hung on a cross at the end of the film (but don't be down: Always Look on the Bright Side of Life). From beginning to end, Life of Brian picks its targets and lampoons them to perfection. The absurdity of warring sects, whose differences are negligible at best, is dissected when the People's Front of Judea adamantly argues its superiority over the Judean People's Front, who they hate even more than the Romans. People who blindly follow leaders, blowing their actions and words completely out of proportion, are mocked through those that follow the Holy Gourd or the Lost Shoe ("Let us, like Him, hold up one shoe and let the other be upon our foot, for this is His sign, that all who follow Him shall do likewise"). Life of Brian is also eerily relevant to this day, with a discussion about how Stan, aka Loretta (Eric Idle), can have the right to have babies, even though he can't have babies because he doesn't have a womb (which is not even the fault of the Romans), that sounds like it could be taken directly from social media.

1. Monty Python and the Holy Grail (1975)

monty-python-and-the-holy-grail
Image via EMI

The best, hands down (quite literally, in the case of the Black Knight (John Cleese)). The plot is straightforward: God sends King Arthur (Graham Chapman) on a quest to find the Holy Grail. It's the events that transpire on this quest that truly makes Monty Python and the Holy Grail memorable, filled with images and wordplay that continue to seep into the public consciousness. Coconuts being banged together to make a horse-clopping sound. The argument about weight ratios and whether a swallow, African or European, could carry a coconut to England. The constitutional peasant (Eric Idle), arguing with Arthur about democracy over the oppression of a monarch who gained the throne by being handed a sword (certainly not a basis for leadership). French soldiers taunting Arthur and his Knights of the Round Table, with your mother was a hamster, and your father smelt of elderberries taunt the most celebrated. The Black Knight who will not allow Arthur to pass, despite losing all of his limbs. The Knights who say Ni. The killer rabbits of Caerbannog, taken out by the Holy Hand Grenade of Antioch. The list goes on, non-stop, right up to the abrupt, surreal ending of the film, where the police arrive and arrest King Arthur and Sir Bedevere the Wise (Terry Jones). Holy Grail is Python at the pinnacle of their silliness, making it slightly more accessible than the (somewhat) deeper Life of Brian. As a testament to its popularity, Monty Python and the Holy Grail would serve as the base storyline for Monty Python's Spamalot, which played on Broadway for 1,575 performances, earning 14 Tony Award nominations and winning three, including the Tony Award for Best Musical.