The 10 Funniest Movies of All Time

We cannot call ourselves film lovers without loving the art of comedy. Comedy is another medium that helps us escape our daily lives and gets us to enjoy life through laughter.

“A good laugh heals a lot of hurts.” –Madeleine L’Engle, Author of A Wrinkle in Time

I make it my mission in life to watch as much good comedy as possible. Thinking about the films I’ve watched over the years that have made me laugh the most, it was hard to narrow it down to only 10!

After much deliberation, here the funniest movies of all time! (in chronological order):

Duck Soup (1933)

The Marx Brothers deliver a comedic gem with this film. Coming off their run in silent cinema, they provide a movie with several scenes that wouldn’t be as funny without sound. Every scene results in gut-busting laughter, from its continuous play on words to their signature slapstick humor. One scene that always gets me going is when Groucho and Harpo match each other’s movements, with the latter trying to trick the former into thinking he is looking into a mirror.  This masterpiece paved the way for decades of comedic “talkies” to come.

Rufus T. Firefly: “…Take a card.” [fans out a deck of playing cards]

Mrs. Teasdale: [picks a card] “Card? What do I do with the card?”

Rufus T. Firefly: “Keep it! I got fifty-one left!”

Monty Python and the Holy Grail (1975)

This movie has amazing “quotability” (yes, I just made up a word…you know what I mean. Work with me). A group of fans could take turns quoting it and end up reciting the whole movie without much difficulty. It never gets old. The British troupe Monty Python, in their first departure from their T.V. show, take us into an utterly silly world where there are no rules (I almost heard John Cleese from Rat Race say that as I was writing it). After all, they make believe that there are such things as homicidal rabbits, clapboards, and a cartoon cave monster in 932 A.D. England. This is perhaps the silliest movie of all time, and easily one of the funniest!

Sir Bedevere: “…and that, my liege, is how we know the Earth to be banana-shaped.”

King Arthur: “This new learning amazes me, Sir Bedevere. Explain again how sheep’s bladders may be employed to prevent earthquakes.”

Animal House (1978)

This movie has influenced the comedies of today. The brilliant minds of Harold Ramis, Douglas Kenney, and Chris Miller come together to pen a story that is so hilarious that it made me want to be a part of a fraternity (in a different universe, that is). This movie revolves around a frat house of a bunch of college-aged delinquents (John Belushi, Peter Riegert, Tim Matheson, just to name a few) and their antics that drive the dean (John Vernon) up the wall. From a toga party that started a trend to the various pranks the Deltas pull, ending with the unforgettable climax of a town parade gone wrong, this comedy brings the laughs that continue to this day.

D-Day: “War’s over, man. Wormer dropped the big one.”

Bluto: “What? Over? Did you say ‘over’? Nothing is over until we decide it is! Was it over when the Germans bombed Pearl Harbor? Hell, no!”

Otter: [to Boon] “Germans?”

Boon: “Forget it, he’s rolling.”

Planes, Trains, & Automobiles (1987)

I will always appreciate this movie for so many reasons. For starters, this was the only time Steve Martin and John Candy got to be co-stars. I know, I know. They were both in Little Shop of Horrors (1986), but they had no scenes together. Secondly, while this film is hilarious, there were a lot of moments where drama prevails over the comedy and the writers made the transition seamlessly. One of the key moments is the scene where Candy explains himself to Martin in a way that makes us shift our empathy toward him: “I like me, my wife likes me, my customers like me.” I will always remember the nighttime highway portion of the film where their car flies between two semis and all the clever angles that show the horror they’re feeling but in a hilarious way. This is also one of my all-time favorite movies and I recommend it to all who want a good laugh with a heart-warming touch.

Del Griffith: “You want to take a shower?”

Neal Page: “No!”

Del Griffith: “…No, I meant, if you wanted to go first or not.”

A Fish Called Wanda (1988)

John Cleese and Michael Palin, both from the Monty Python troupe, reunite in this timeless movie about a jewel heist that results in one disaster after another. They are joined by Jamie Lee Curtis and Kevin Kline, in his Oscar-winning role. What I love about this movie is that every one of the main characters is funny, and there is never a dull moment when they intertwine. Cleese gets more credit, though, for he wrote the screenplay. I also love the peculiarities of every character, from Kline being an assassin with a love for philosophy to Palin having a serious stuttering problem, except when he’s talking to his fish…called Wanda (coincidentally, also the name of Curtis’s character). For those who love a movie about a comedy of errors, this one is worth watching!

Otto: “Don’t call me stupid.”

Wanda: “Oh, right! To call you stupid would be an insult to stupid people!”

Groundhog Day (1993)

Bill Murray bestows upon the world another comedic masterpiece in this film that is more funny than anything, but also has a lot of heart. He plays a weatherman stuck in a 24-hour time loop while in Punxsutawney, PA to cover the annual Groundhog Day festival. On top of not wanting to be there in the first place, he lives out each cold and miserable day over and over again, which drives him mad, but there is nothing he can do about it. Andie MacDowell plays the producer of the T.V. station that Murray works for, and the object of his affection. She is what keeps him going when he eventually decides to pursue her romantically. Director Harold Ramis balances out the film’s comedic and romantic aspects so well. Is it any wonder why my wife and I watch this movie every February 2nd?

Phil: [to the cop after being pulled over after some crazy driving] “Yeah, three cheeseburgers, two large fries, two chocolate shakes and one large Coke.”

Ralph: [to Phil] “And some flapjacks.”

Phil: [to Cop] “Too early for flapjacks?”

Dumb and Dumber (1994)

The combination of Jim Carrey and Jeff Daniels proves to be one of the best comedy duos of all time. Even though the pair plays a couple of guys whose collective brainpower couldn’t light a match, they deliver a comedy that I still watch religiously to this day. I was 11 years old when I saw Dumb and Dumber for the first time, and it made me laugh endlessly. Carrey and Daniels go on a cross-country trip to return a briefcase. While it’s a mystery how these two could even drive a car, the pitfalls and the people they come across proved to be hilarious. This is another comedic classic that I quote a lot, and I find that others do the same. I would start with the line, “You heard him, those were his last words,” and without fail, the other would finish with, “Not if you count the gurgling sound.”

Harry: “I can’t believe we drove around all day and there’s not a single job in this town. There’s nothing, nada, zip!”

Lloyd: “Yeah, unless you want to work 40 hours a week.”

The Big Lebowski (1998)

This is the ultimate comedy of our generation and is quite easily the funniest movie of all time (okay, so my wife disagrees with me…but this is my blog, not hers). The Coen brothers put their great minds together to add another great film to their impressive resume – definitely their best. It also impresses me how broad their storytelling range is: from the sheer seriousness of Miller’s Crossing (1990) to the dark comedy/thriller Fargo (1996). While this movie has the elements of a thriller, it spoofs the whole film noir genre.

Jeff Bridges plays The Dude, a middle-aged, pot-smoking slacker who takes charge in his life to get back his beloved rug that was sullied by one of the goons who broke into his place thinking he was a different Mr. Lebowski. That alone is a great tagline to sell a film. However, it’s not that easy for The Dude, as he gets in too deep when he gets wrapped up in a kidnapping scheme. With the help of his buddies, played by John Goodman and Steve Buscemi, The Dude tries to piece it all together, because that’s worth the price of a rug. From its numerous one-liners (not for the faint of heart, for there are a lot of F-bombs), hilarious scene outcomes, and performances, The Big Lebowski is the top of the line as far as comedies go.

Walter: “He lives in North Hollywood on Radford, near the In-N-Out Burger.”

The Dude: “No, the In-N-Out Burger is on Camrose.”

Walter: “Near the In-N-Out Burger.”

Donny: “Those are good burgers, Walter.”

Walter: “Shut the f*** up, Donny.”

Office Space (1999)

From being stuck at work watching the clock tick, to wanting to break away for lunch as early as possible, anyone who has ever had a job – particularly an office job – can relate to some aspect of Office Space. Mike Judge departs from the cartoon saga Beavis and Butt-Head to make his live-action debut – one that is worth watching repeatedly (again, my wife disagrees).

The story revolves around a small group of employees at a computer software company that grow tired of their jobs and the lack of respect they get from their superiors. They conspire to rip off the company by hacking into their database and embezzling funds. From a funny plot to oodles of memorable dialogue, this one is worth watching – you won’t be disappointed.

Peter: “So I was sitting in my cubicle today, and I realized, ever since I started working, every single day of my life has been worse than the day before it. So that means that every single day that you see me, that’s on the worst day of my life.”

Dr. Swanson: “What about today? Is today the worst day of your life?”

Peter: “Yeah.”

Dr. Swanson: “Wow, that’s messed up.”

American Movie (1999)

Lastly, we have American Movie, a documentary that chronicles the making of a low- budget (or no-budget) horror movie. I don’t normally go for documentaries, but this one is so funny and out there, it gets me laughing hysterically every time. The people in this movie are genuine and that’s what makes this so worth watching. Milwaukee native Mark Borchardt dreams of being a filmmaker, with horror being his genre of choice. He made a bunch of short horror films in “home movie” quality growing up. He has completed a feature-length screenplay and wants to put it into production, but he needs to complete his abandoned project, Coven, first. His childhood pal Mike Schank helps in any way he can, but numerous obstacles (like gambling and alcohol) get in their way. Other obstacles include issues with the editing machine, Mike’s uncle who can’t memorize his lines and having to pick up the producer from jail. Despite it all, good fun and laughs abound. American Movie just may inspire us all to make a movie of our everyday lives, but who’s to say that it will be as funny as this one.

Mark Borchardt: “Do you think this is a little bit cathartic for you?”

Mike Schank: “Uh, very cathartic, Mark.”

Mark Borchardt: “Do you know what cathartic means?”

Mike Schank: “No.”

Happy watching!