Ranking The 10 Best 'Monty Python's Flying Circus' Sketches On The Show's 50th Anniversary

It's not hyperbole to note that the Monty Python comedy troupe changed the state of comedy. The six men who made up the group — Graham Chapman, John Cleese, Terry Gilliam, Eric Idle, Terry Jones, and Michael Palin — came together as an unstoppable force that reshaped what TV comedy could be, before they then upended expectations of what film comedy could be in the late 1970s. But it all started with the sketch TV series Monty Python's Flying Circus, which turns 50 this month. That's when the first episode aired on the BBC in 1969, providing a brief glimpse into what the future of sketch comedy, years before Saturday Night Live was a blip on anyone's mental radar. So now, let's look at the 10 best sketches in Python history. One important caveat: these are only sketches from the show, nothing from the many brilliant Python films. 

10. “Funniest Joke in the World,” Season 1 (1969)

The first episode of Monty Python's Flying Circus is, like the very concept of a sketch-comedy series would suggest, a bit hit or miss. Not every moment of the first half-hour is hilarious, but the climactic sketch is still incredibly funny. In the sketch, we watch a fairly unassuming man (Palin, naturally) writing in his room before he apparently lands upon the funniest joke in the world. How do we know it's the funniest joke in the world? Not just because the stentorian narrator tells us it's so, but Palin's character reads it to himself and then laughs himself to death. Within a couple minutes, the sketch has turned into a wartime story in which the Allies use the joke as a major weapon in the later days of World War II. The cascading goofiness of the sketch — plus its various settings and characters — is still a high watermark of Python comedy.

9. “Cheese Shop,” Season 3 (1972)

Not all of the sketches from Monty Python's Flying Circus followed the same setup of John Cleese being continually more and more frustrated at the straight-man calmness of Michael Palin, but two of the show's best-ever sketches have that similar DNA. Here, Cleese plays a man who walks into a cheese shop. All he wants is some cheese. And so, he asks for a specific kind, only to find that the shop has none of it. And then he runs down...a lot of different types of cheeses, none of which they have. What makes the sketch so funny, aside from its rapid-fire pacing as Cleese lists out — literally — 44 different kinds of cheese, are Cleese's fussy replies in between. 

8. “The Spanish Inquisition,” Season 2 (1970)

The notion of the fourth wall being broken sometimes went as deep as characters within a sketch being frustrated at the other characters in their sketch. Such was the case with the Spanish Inquisition sketch from Monty Python's Flying Circus's second season. We first watch a fairly dry bit of melodramatic acting in an English period setting before one of the actors (Chapman) says the key phrase: "I wasn't expecting the Spanish Inquisition!" In pops a group of extremists, led by Palin's mustachioed inquisitor, replying "Nobody expects the Spanish Inquisition!" From that point, he and his comrades lose the thread, continually adding onto the chief ingredients — fear, then fear and surprise, then fear, surprise, and so on. The absurdist sketch stands out because the other characters get more and more vexed each time the inquisitors appear.

7. “Mr. Hilter,” Season 1 (1970)

No, that's not a typo. This is a sketch about a perfectly nice man named Adolf Hilter. According to his friend Ron Vibbentrop, he's running in the Minehead by-election as part of the National Bocialist Party. OK, but seriously: this sketch is based on the premise of what would have happened in the early 1970s had a handful of the worst, most evil and odious Nazis hidden in plain sight and attempted to adopt the tenets of the Nazi Party in very small English elections. (What a crazy idea that has definitely no resonance in 2019 politics. Ahem.) What makes this sketch so funny and absurd is how painfully obvious it is who this...uh, Hilter person is, and how desperately Hilter (Cleese) and the others try to hide it. Perhaps the funniest part is near the end, as a young mother (Idle) tells a film crew, "I gave my baby to him to kiss, and he bit it on the head!" You can't hide your true colors, fake name or not.

6. “Ministry of Silly Walks,” Season 2 (1970)

If you know Monty Python's Flying Circus, you may well know it for the image of John Cleese, dressed to the nines, in the middle of a long-limbed gait down the streets of London. That, of course, is from this sketch, all about a man who works for the Ministry of Silly Walks. The dialogue in this sketch isn't that important at all — though it's once again Cleese and Palin on screen, the latter playing a man who wants to have his own purportedly silly walk given a government grant. The physical humor of it, as we watch how a simple walk around an office turns into a miniature performance of flailing limbs, spilled food, and knocked-over office supplies, makes this truly hilarious.

5. “Self-Defense Against Fresh Fruit,” Season 1 (1969)

John Cleese excelled at playing authority figures on Monty Python's Flying Circus, never more so than when he got to play such leaders who have a screw or two loose. In this sketch, he plays the militaristic teacher of a class meant to teach grown men self-defense when they're attacked by an assailant wielding...fresh fruit. As it turns out, we're not watching his first class with these students. They'd rather learn about fending people with real weapons, and they've been in enough sessions to list off the fruit they've already learned about, such as cherries ("Red and black?" "Yes."), plums, and mangoes in syrup. But the group hasn't learned about bananas, and so we get to watch the murderous farce (which involves gunplay, of course) play out. This show rarely blended wordplay with silliness so well.

4. “Nudge Nudge,” Season 1 (1969)

The "Nudge Nudge" sketch is building to what is perhaps an obvious punchline, but it's no less funny because of the zeal with which Eric Idle dives into his lecherous character. Two men — Idle and Jones — are at a bar, and the former asks seemingly lascivious questions of the latter and his unseen wife. The more Idle's character keeps making innuendos — "Well, she's been around, eh? Been around?" to "Your wife interested in, uh, photographs? Candid photographs?" — he eventually gets to the point, wanting to know what it's like to sleep with a woman, because he's clearly never had the pleasure. No better way to end that sketch than the episode in question does: by ending.

3. “Homicidal Barber/Lumberjack Song,” Season 1 (1969)

You likely already know about the Lumberjack Song, in which a young man (Palin) sings about how much he's always wanted to be a lumberjack, and how the song devolves into his reveal of his latent homosexuality. But the sketch leading into the song is just as funny, as the character played by Palin is seen as a barber with a specific problem: when he thinks about cutting hair, let alone holds a pair of scissors or a straight razor, all he thinks about is letting loose streams, rivers of blood by "cutting, cutting, cutting" into the bodies of the people whose hair he's supposed to cut. The sketch then transitions into the song, simply heightening the silliness to a new, even odder level with an earworm that climaxes with the singer talking about "pressing wildflowers".

2. “Upper Class Twit of the Year,” Season 1 (1970)

The era of Brexit has made it so this sketch feels even more timely. As narrated by an offscreen announcer voiced by Cleese, the Upper Class Twit of the Year is an annual competition in which five young men compete to be the biggest twit of all. Each of the main performers in Python (Terry Gilliam appeared in some sketches, but his work were the various animated interstitials in each show) plays a twit of a certain kind, gleefully stupid from top to bottom. The various activities in the competition, from jumping over a row of tiny matchboxes to waking someone up from their bed, are truly inane. It's all coupled with Cleese's intense shouting to make for a sly, satiric look at British men of the era. Or, British men of today.

1. “Dead Parrot,” Season 1 (1969)

Here is the brilliance of Monty Python boiled down into a nutshell. The premise of this sketch is maddeningly simple: a man enters a pet shop, angry because the parrot he bought from the shifty proprietor is dead, and the pet-shop owner refuses to acknowledge the obvious. The tetchy byplay and chemistry between Cleese, as the customer, and Palin, as the owner, is the kind of thing that you can see time and again in plenty of Python sketches (including a few others on this list). But it just does not get better than Cleese's apoplectic fury at Palin's pet-shop owner's excuses, getting more and more ridiculous throughout. The "ex-parrot" set the tone for Python's wordy sketches.