Top 10 Funniest Movies of All Time

Greetings, reader!

Tomorrow is the 40-year anniversary of Monty Python's The Meaning of Life (1983), the third and final Monty Python film, being released. In honor of this comedy classic, I'm taking a look at the very gems of the comedy genre, and ranking the 10 funniest films of all time (in my humble opinion). Just to be clear, this isn't the same as 'the greatest overall comedy films', but purely the ones that are the very funniest, no matter what tier of cinema they come from. I hope you enjoy!

Here are my honorable mentions: Deadpool (2016), Dr. Strangelove or: How I Learned to Stop Worrying and Love the Bomb (1964), Due Date (2010), Ferris Bueller's Day Off (1986), Home Alone (1990), In Bruges (2008).

10. 21 Jump Street (2012)

"One particle of unobtainium has a nuclear reaction with the flux capacitator - carry the '2' - changing its atomic isotoner into A RADIOACTIVE SPIDER. Fuck you, science!"

With this ultimate "watch it on a Sunday night or an airplane" flick, it's mainly about Jonah Hill and Channing Tatum's collective chemistry, individual comedic talent, and amusing reversal of expected roles. Also, Ice Cube being Ice Cube adds monumental comedy value. Having the scene that ousted Blues Brothers (1980) as the funniest car chase sequence in cinema doesn't hurt either. And then there's the undercover cop storyline's way of combining Brooklyn Nine-Nine (2013-2021) style police comedy shenanigans with American Pie (1999) style high school shenanigans. So, it's a whole lot of things, really. Even the soundtrack has great comedic timing.

9. Tag! (2018)

"What's the difference between Episcopalian and Lutheran?"

"Episcopalians don't eat fish"

"That's pescatarian, that's...not a religion"

"They're all fanatics, I don't know"

The interaction quoted above is justification enough for a top 10 slot. Besides that fantastic piece of dialogue, Tag! keeps one amused and entertained with its incredibly real-life-inspired premise (a group of friends who started an ongoing game of tag as kids, and have continued to play it and take it seriously way into adulthood) and its beyond-hilarious cast. Hannibal Buress' stoner humor, Jon Hamm's down-to-earth antics, Ed Helms' chaotic brand of comedy, Jeremy Renner's over-the-top action hero aesthetic and Jake Johnson's completely baffling, absurd and unique style of Jake Johnson comedy make for one hell of a combination - each of the main characters is very, very funny in their own way.

8. Scary Movie (2000)

"If you could have spoken to her before she died, what would your last words to her have been?"

"Run, bitch, run!"

The big difference between a "Top 10 best movies that happen to fall under the comedy genre" list and a "Top 10 comedies, based purely on how funny they are" list is that some truly dumb but inexplicably hilarious pseudo-cinema can make it onto the latter while having no business near the former. Chief among these gems is the cult-classic horror parody Scary Movie.

It says a lot that the film's chief source of parody is Wes Craven's Scream (1996), which in itself is not very serious and a semi-parody of the slasher genre on a meta level. And the level of humor in Scary Movie is exactly what you can expect from something that is essentially a parody of a parody. But dammit if the dumb jokes don't make me laugh out loud every time, as they tap into something primal in the human sense of basic comedy. Jokes like the "Amistad 2" trailer, the "WAZZUUUP" sequence and the film's unforgettable twist ending are as objectively funny as they are unapologetically stupid. I've talked a lot about "watch this on a Sunday night or an airplane" films, but this one falls more into the "watch this while high at 2 A.M. at a noisy house party" category.

7. The Hangover (2009)

"Counting cards is a foolproof system"

"It's also illegal"

"It's not illegal, it's just frowned upon, like masturbating on an airplane"

"I'm pretty sure that's illegal too"

Forbes once made a pseudo-scientific study on what the funniest movies of all time are, based on the average "laughs per minute" caused in different kinds of viewers. Out of all the movies tested, The Hangover came in second place, averaging at 2.4 laughs per minute. Just think about that for a moment - the average minute of The Hangover will make you laugh, out loud, multiple separate times. That's quite the achivement.

Yeah, The Hangover is pretty great - Justin Bartha is the comedic straight man, Bradley Cooper and Ed Helms deliver funny and memorable performances and Zach Galifianakis knocks it out of the park (not to mention Ken Jeong and Mike Tyson's delightful supporting performances).

6. Hot Shots! (1991)

"Admiral Benson!"

"Really? That's my name too!"

Ah, back to the dumb variety. The humor in Hot Shots! may be simple, but there's no limit to how effective it is. From the film's opening moments hilariously spoofing the iconic Top Gun (1986) opening, through unforgettable gags like "I have my father's eyes" and the tears-of-laughter-inducing culinary sex scene, all the way to the glorious ending, this top tier parody film is one for the ages. Charlie Sheen is fantastic in the lead role, and all of the hilariously stupid (or stupidly hilarious) humor just works like a charm while having multitudes of re-watch value.

5. Police Academy (1984)

"What's wrong with this man?"

"There was gunplay, Sir. And he missed it"

And so we arrive at the very essence of slapstick. A movie where the myriads of humor are matched only by the escalating cruddiness of the sequels, Police Academy is a silly classic where even the score and especially main theme are among the funniest of their kind.

But what really makes the movie into such a comedic tapestry is the cast of characters. From Mahoney's (Steve Guttenberg) bad-boy antics and Hightower's (Bubba Smith) over-the-top presence, through Jones' (Michael Winslow) hilarious sound effects and Hooks' (Marion Ramsey) vocal struggles, all the way to Fackler's (Bruce Mahler) bumbling antics and Tackleberry (David Graf) somehow being such a flawlessly executed 'gun nut' character that even I find it funny, the main group of characters is an unforgettable one, with each one's comedic hijinks playing off each other.

4. Clerks (1994)

"Thirty-seven! My girlfriend sucked thirty-seven dicks!"

"In a row?"

That exchange alone deserves Kevin Smith's masterpiece a spot on this list. But, yeah, in all its crudeness, Clerks is top tier comedy. Following a day in the life for two store clerks, the film finds its comedic voice through its chill atmosphere - much like the famous 'show about nothing' concept working in Seinfeld (1989-1998), Clerks bathes in the delight and amusement of life's little things.

The dialogue between the main characters, as they argue about movies and take roof-hockey breaks amidst their workday, is as sharply funny as it is authentically laid-back. The interactions with the side characters, such as Jay (Jason Mewes), Silent Bob (the man himself) and a vast array of customers, are the icing on the cake.

3. Monty Python's The Meaning of Life (1983)

"Hello, and welcome to the Middle of the Film, the moment where we take a break to invite you, the audience, to join us, the film-makers, in 'Find the fish'"

Ah, the movie of the hour! Turning fourty years old tomorrow, The Meaning of Life is one bizarre film, even by Monty Python standards. But my God, it's hilarious, in a way quite like no other. I mean, already the film's structure has some fantastic comedic genius to it - the semi-musical style with multiple original songs, while jumping from skit to skit as they tie together just enough to feel like a cohesive movie, made all the better by the wonderfully psychedelic fish tank interludes. Also, this is the one movie where an announcer welcomes the viewer to the middle of the film (and later to the end of the film), so there's that.

The absolute hilarity of the structure is completely matched by the substance of the various sequences. The Crimson Permanent Assurance buildings crashing into each other, the 'Every sperm is sacred' song, everything Eric Idle says and does, the list goes on. The film makes some majestic humor out of its deeper-than-previous-works -subject matter, while also going deeper into it than one might expect - and, once it has reached some quite philosophical ponderings, uses them to milk even more comedy gold out of this treasure trove of laughs.

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

"Crucifixion?"

"Yes"

"Good. Out of the door, line on the left, one cross each. Next! Crucifixion?"

"Yes"

"Good. Out of the door, line on the left, one cross each. Next! Crucifixion?"

"Eh, no, freedom"

"What?"

"Freedom for me. They said I haven't done anything and I could go free and live on an island somewhere"

"Oh! Oh well that's jolly good, well, off you go then"

"Nah, mate, I'm pulling your leg, it's crucifixion really!"

Laughing so hard that you cry from laughter is a rare and beautiful occurrence. And I have never laugh-cried as hard, in my life, as I did when I watched the final moments of Life of Brian unfold for the first time. The film had been hilarious enough leading up to it (the stoning sequence, the Judean Peoples' Front, the 'What have the Romans ever done for us' dialogue, you name it), but that ending just seals the deal. Is there anything in this world that's funnier than Eric Idle getting a bunch of crucifixion victims to gleefully sing 'Always look on the bright side of life' as they hang from the crosses?

Well, I can think of one funnier thing off the top of my head, but that'll come up in today's #1.

But, yeah, Life of Brian is as amusing with its individual skits as it is with the larger theme as the film makes light of events from the New Testament and religion in general. The film sure got its share of criticism back in the day, but I mean really, when considering how many have been killed in the name of religion, I can't see how anyone would see 'six British comedians not taking religion all that seriously' as a major problem after centuries of 'people taking religion, like, WAY too seriously'. I've been glad to hear that many modern Christians do enjoy the film as a light-hearted take on it all.

1. Monty Python and the Holy Grail (1975)

"What makes you think she's a witch?"

"She turned me into a newt!"

"A newt?"

"...I got better"

Is it a bit overkill to have the three Monty Python feature films as my picks for the literally three funniest movies of all time? No, it is not, and they deserve it. In my honest opinion, the least funny Python film really is funnier than any non-Python film I've seen, which speaks volumes of the comedic genius of this fantastic group. And the best of the bunch is 1975's Monty Python and the Holy Grail.

You know that feeling that you get when Nino Rota's music lays the atmosphere for the opening moments of The Godfather (1972) or when the yellow opening text blasts onto the screen in Star Wars (1977)? You know, the 'I'm about to watch Great Cinema' -goosebumps? I bring this up because this film starts with what can only be described as comedy's equivalent to this dramatic feeling. When I watched The Holy Grail for the first time with my brother, we hadn't seen any Monty Python skits and knew pretty much nothing about the group, just that these movies are among the highest-rated comedy classics so we should probably watch them. And just from the wonderfully escalating opening credits, it was pretty clear that we're watching something life-changingly funny, something on the next level.

There's just so much to love here. You've got insanely hilarious running jokes, like the low-budget take on cavalry scenes where everyone rides imaginary horses, and the random subplot where modern-day policemen are thrust into the medieval story. You've got mind-blowingly imaginative comedy that no one else could come up with, like the monster dying because 'the animator suffered a sudden heart attack' and the Holy Hand Grenade. You've got unforgettable and hysterical characters, like John Cleese's Black Knight, Terry Gilliam's Bridgekeeper and everyone Eric Idle plays. You've got uniquely Monty Python -style humor, such as the scene where the bridgekeeper ends his first set of riddles with a ridiculously difficult question, then twists the expectations by ending the next set with the amusingly easy "what is your favorite color?" - only for a laugh-out-loud double twist to occur, as Sir Galahad (Michael Palin) somehow fumbles his response ("Blue! NO, WAIT, YELLO...") and is thrown off the bridge.

And, yes, I mentioned in my Life of Brian description that there is one thing I could think of that is even funnier than the crucifixion sequence in that film; I believe Monty Python and the Holy Grail to contain the single funniest scene in all of cinema (or television, literature or theater, for that matter). The scene in question is the King of Swamp Castle (Michael Palin) ordering his guards (Eric Idle and John Cleese) to stay and guard Prince Herbert (Terry Jones), but they keep misunderstanding the order. I have yet to see a better comedic payoff than the guards, after getting the simple instructions wrong in every possible way, finally seeming to understand - until the King leaves the room and they start to leave with him, proving that they're still not getting it. Comedic genius at its highest level.

Thank you for reading! Tune in next week as I begin the second edition of a special music-themed month, kicking off with next Thursday's post where I rank the albums of The Beatles!