The famed British comedy troupe Monty Python starred in a total of five movies throughout their tenure, ranging from timeless classics to underappreciated gems. They made narrative films and sketch compilations; movies shot on location and concert films recorded live; some movies had lighthearted humor, some with shockingly twisted humor, and others with a mixture of both. When bringing their particular brand of surreal humor to the big screen, the troupe tackled bigger subjects like the Arthurian legend, the origins of Christianity, and the meaning of life. Not all of their movies are bona fide masterpieces like Monty Python’s Life of Brian, but there’s something special in each of them.
The Pythons’ influence can still be seen across the comedy landscape today. They’re often referred to as the “Beatles of comedy,” (via The Atlantic) because they marked a watershed moment in the history of the art form. The term “Pythonesque” has become synonymous with the most hilarious absurdist comedy shows, and that style has been adopted by everything from The Simpsons to South Park. The Pythons’ movies were an important factor in attracting a worldwide audience. Some of the troupe’s movies rank among the greatest comedies ever made (via BBC), like Monty Python and the Holy Grail, while others have been forgotten about, like Monty Python’s The Meaning of Life.
And Now For Something Completely Different (1971)
The title of the Pythons’ first feature-length release, And Now for Something Completely Different, feels disappointingly ironic. There’s nothing “completely different” about this movie; it’s a compilation of sketches that had already appeared in the best episodes of Monty Python’s Flying Circus. Some of the transitions between the sketches are different because the order has been changed, but the sketches themselves are the same. The movie was intended for American viewers who hadn’t yet seen the series. These days, with DVDs and YouTube and streaming, Python’s best sketches are readily available to audiences across the globe.
And Now for Something Completely Different features some of the most iconic sketches from the Pythons’ TV show – from “The Dead Parrot” to “The Lumberjack Song” to “The Funniest Joke in the World” – but it’s more of a “greatest hits” album than a movie. And Now for Something Completely Different would be effective as an introduction to Monty Python’s funniest sketches, but to anyone familiar with their work, it’ll feel like a rehash of old material. It’s as if The Simpsons Movie had just compiled all the best bits from the series into a feature-length clip show.
4Monty Python’s The Meaning Of Life (1983)
Of the three Python movies drawn from original material, Monty Python’s The Meaning of Life is the clear underdog. While Holy Grail and Life of Brian appear on many best comedy movie lists, The Meaning of Life is sadly almost never mentioned. Generally considered to be the outlier and not as flawless as their other films, The Meaning of Life is an underrated gem. It’s the darkest Python movie by far – in one sketch, a pair of paramedics remove the organs of card-carrying organ donors while they’re still alive – so Python fans with a pitch-black sense of humor are more likely to enjoy this one.
The Meaning of Life is a mixed bag of great sketches and unmemorable ones. It gets off to a slow start with The Crimson Permanent Assurance, a 16-minute swashbuckling spoof that wears out its welcome. But this movie features some of the all-time best Python sketches, like “Every Sperm is Sacred” and a sex ed class where the students watch their teacher having sex with his wife. But these are all in the first half. It takes a bizarre turn after the fourth-wall-breaking “Find the Fish” segment that marks the midpoint and ends on a morbid note with the Grim Reaper taking a group of ill-fated diners to the afterlife.
3Monty Python Live At The Hollywood Bowl (1982)
The only Python movie recorded live, Monty Python Live at the Hollywood Bowl, is one of the funnier movies in the concert film genre. Like And Now for Something Completely Different, Live at the Hollywood Bowl consists mostly of sketches that were already seen in the TV series. But unlike And Now for Something Completely Different, Live at the Hollywood Bowl puts a fresh spin on each sketch with different dialogue and recast roles. The huge crowds of diehard fans gathered at the legendary amphitheater give the sketches a lively energy that was missing with the limited studio audience of the original series.
2Monty Python And The Holy Grail (1975)
The troupe’s first original feature-length effort and, many would argue, Monty Python’s best film, Monty Python and the Holy Grail is a masterpiece from start to finish, frequently mentioned in the same breath as comedy greats Airplane!, Ghostbusters, and Blazing Saddles. Like any fantastic comedy, Monty Python and the Holy Grail doesn’t miss an opportunity for a joke; it even has gags in the opening credits. From the Trojan Rabbit to the Killer Rabbit of Caerbannog to the Black Knight who refuses to admit defeat, this surreal take on the Arthurian legend is full of unforgettable gags.
The meta-humor of Monty Python and the Holy Grail was way ahead of its time, as the film constantly points out the artifice of cinema. Instead of riding real horses, Monty Python parodies King Arthur and his knights, as they just trot their feet while their squire clacks coconut halves together. When a scene is dragging on, the characters from the other scenes tell them to “get on with it!” The whole thing culminates in a hysterically anticlimactic ending: just as Arthur and co. are charging into battle, contemporary cops arrive to break up the fight and arrest the knights. They shut off the camera and the movie just ends.
1Monty Python’s Life Of Brian (1979)
The Pythons’ second movie, Life of Brian, is the resounding hit that brought the troupe to a global audience. At the time of its release, Life of Brian generated plenty of controversy when its fair and balanced satire of the bureaucracy of religion was mistaken for blasphemy, but that just brought more attention to the film. Life of Brian has as many funny scenes as Holy Grail but with sharper satire and a more tangible story arc. Whereas Holy Grail is loosely built around the Arthurian legend with digs at the monarchy and the unreliability of historical accounts, Life of Brian is an incisive takedown of organized religion.
Life of Brian has much tighter plotting than its Monty Python predecessor. Holy Grail tags jokes and sight gags and non-sequiturs onto King Arthur’s quest to find the Grail; Life of Brian sets up its story with a specific joke engine as the wrong man is hailed as the Messiah and that mistaken identity follows him for the rest of his life. The ending of Holy Grail is hilariously anticlimactic, but Life of Brian ends on the perfect punchline: Brian being wrongfully crucified while his fellow cross-bearers sing “Always Look on the Bright Side of Life.”