We live in a world of high-stakes controversy over issues that, a few years ago, would have seemed nonsensical to debate. Giving tax cuts to banks? Reopening coal mines? I know it’s hard to remember, but we used to live in a world where things like this would have been considered beneath us as a nation. Those were the days.
Given our culture’s red-line status on internal conflict, and its recent track record in handling differences, you would be right to wonder what the hell I think I’m doing, claiming to have listed the greatest comedy films of all time.
More Great Movies
Comedy is, after all, perhaps the most controversial category in film. Don’t believe me? Next time you’re at a party, let it be known throughout the gathering what you consider a good comedy movie, or even just your favorite. Then position your back against the wall (for safety) and prepare to endure an onslaught of aggressive protestation of your choice. People are protective of their brand of humor, man.
And so now we get to the actual list, which I’m sure most of you will not like. But if you’re new here and nobody’s explained the rules yet, I’m counting on you to remember two things as you read:
- This is one writer’s opinion, and disagreement is welcomed. These are just movies we’re talking about. Save your strength.
- At the end of the day, delving into this controversy was your choice. Nobody held a gun to your head to read this article. (I hope.)
Here we go. In no particular order (because I’m not that brave), here are the best comedy films of all time.
A Night at the Opera
“When I invite a woman to dinner I expect her to look at my face. That’s the price she has to pay.”
Let’s kick things off with an undisputed icon of comedy. Three of them, actually. The Marx Brothers, a real-life family that rose to fame as a vaudeville troupe then took Hollywood by storm with their series of raucous comedy movies. A Night at the Opera is a contender for their very best, thick with rapid-fire wordplay, ingenious insults, and racy innuendo that they only got away with because the film production business hadn’t been regulated yet. In this film, Groucho Marx plays Otis B. Driftwood, the squirrelly business manager for a wealthy opera investor, while brothers Chico and Harpo Marx play the bumbling sidekicks of a humble background singer who is on the other side of a love triangle with a famous tenor. All of them end up on a steamer ship sailing from Italy to New York, where hijinks ensue. The three Marx Brothers end up coming together in a plot to sabotage the opera’s opening night so that the arrogant tenor will be replaced by the background singer. If you’re confused, don’t worry — the plot isn’t so much the point in this movie as the frenetic pacing that moves the brothers from one gut-busting situation to another. As amazing as the Marx Brothers are, their zany antics wouldn’t be half so hilarious without straight man … excuse me, woman … Margaret Dumont, who finds a hundred different ways to look aghast as the brothers run circles around her hand-wringing image of propriety, dealing out embarrassment, outrage, and general chaos.
Blues Brothers
“106 miles to Chicago, we got a full tank of gas, half a pack of cigarettes, it’s dark, and we’re wearing sunglasses. … Hit it.”
This is SNL founding legend John Belushi in his comedic prime, which is to say, before his untimely passing. As retired musician Jake Blues, Belushi says more with an eyebrow in this movie than most actors can muster in three acts. Pair him with Dan Aykroyd’s Elwood Blues, and you have cinematic and comedic gold. They got the band back together and they gave us a million laughs in the process, each with their own idiosyncratic take on goofball physical comedy and subtle-as-a-razor’s-edge delivery. As if that weren’t enough, The Blues Brothers is a roll call of celebrities from the late 70s, each cameo appearance clearly relishing their chance to get a piece of the action. And don’t get us started on the musical performances by the likes of Aretha Franklin, Ray Charles and Cab Calloway, with Jake and Elwood grooving hard in the background.
Monty Python and the Holy Grail
“Your mother was a hamster and your father smelled of elderberries!”
Another easy pick for the comedy “GOAT” list. The four lads from London trade off the numerous roles of King Arthur and his round table of knights, including well-known figures of legend such as Sir Lancelot and Sir Galahad, as well as lesser known heroes like Sir Robin the Not-Quite-So-Brave-as-Sir-Lancelot and Sir Not-Appearing-in-this-Film, as they caper around the English countryside in search of the Holy Grail. Along the way, they encounter villains such as the knights who say “Ni!”, a three-headed knight, a castle occupied by rude French soldiers, and a ferocious rabbit. But don’t get any ideas about a linear plot — the movie meanders down all sorts of absurdist sidetracks, with plenty of anachronisms, snide camera commentary, looks behind the scenes, and a musical number for no good reason at all. In other words, a lot easier to follow than the Monty Python TV show.
Tommy Boy
“No wait, it’s gotta be your bull.”
It wasn’t easy to pick which Chris Farley movie to put on this list … Oh, who am I kidding? It was super easy. The prize alumnus of ’90s-era SNL made a lot of great buddy comedies, but this one has to be the most endearing of them all. In it, new college graduate Tommy Callahan returns home to find he must save the family business by stepping into his father’s shoes, with a little guidance from snide secretary David Spade. A cross-country trip’s worth of hilarious shenanigans ensue, as well as severe damage to a 1967 Plymouth Belvedere GTX. Never has Farley and Spade’s frenemy rapport been sharper — like a late twentieth century Laurel and Hardy, the two were born to work together. We dare you to watch this movie for the first time and not die laughing.
Caddyshack
“I was born to rub you, but you were born to rub me first. What do you say we take this out on the patio?”
This movie has it all. Chevy Chase playing the dude we all wanted to be — a rich ladykiller with effortless sports prowess. Bill Murray playing a dogged and dimwitted slacker with a Zen master’s dedication to groundskeeping. Rodney Dangerfield playing himself. Like so many comedies, the actual plot is pretty well beside the point, as is the main protagonist — it’s all the so-called “side characters” that make this comedy gold.
Doctor Strangelove, Or: How I Learned to Stop Worrying and Love the Bomb
“Gentlemen, you can’t fight in here! This is the war room.”
Since the cinematic world considers this a comedy, it gets spot number 3 on our list. To call a Kubrick picture a comedy seems an injustice, despite the numerous absurd scenes that could only cause one to smile, if not outright laugh. Peter Sellers, Peter Sellers, Peter Sellers. An actual genius who plays three parts in one of the greatest performances in the history of cinema. We only wish the nuclear holocaust theme of this movie was more absurd in the year 2020.
The ‘Burbs
“In Southeast Asia, we’d call this kind of thing bad karma.”
There are Tom Hanks lovers out there who have never seen him in the funniest role of his career. To those people, allow us to present The ‘Burbs. Nothing too exciting happens at the end of a cul de sac on a normal summer weekend, right? Wrong. Bruce Dern as the longing veteran with the trophy wife delivers a legendary performance to support Hanks and Rick Ducommun as the other incompetent neighbor. You’ll laugh your ass off as sure as a femur is a human leg bone.
National Lampoon’s Vacation
“Ah, That’s the Mississippi. The mighty Mississip. The Ole Miss, the Old Man.”
In 1979, an apocalyptic blizzard trapped writer John Hughes in his house. To pass the time, Hughes wrote a short story about a Midwestern family taking an unfortunate trip to Disneyland, tracking his story along the highways on a Rand McNally road atlas. This, friends, is how the world got the Family Truckster, Aunt Edna, “We like to send out a mailer,” dog piss sandwiches, The Old Miss, The Old Man, directions, the greatest sex symbol of the 80s in a red Ferrari and naked in a pool, Eddie, a non-CGI actual eighties station wagon flying 80 feet through the air, dead aunt roof racks and a dog that tried to keep up for the first few miles. By the end, your stomach will be more worn out than that sad station wagon is by the end of the movie.
The Big Lebowski
“This is a very complicated case, Maude. You know, a lot of ins, a lot of outs, a lot of what-have-yous.”
Loosely based on the detective novels of Raymond Chandler, this Cohen Brothers comedy follows consummate slacker Jeffrey “The Dude” Lebowski, who is rudely interrupted mid-toke by a pair of thugs who have mistaken him for a wealthy philanthropist with the same last name. When they realize their error, one of them takes a contemptuous piss on The Dude’s rug, sending The Dude on a mission to get a replacement from the rich guy they mistook him for. But the Big Lebowski has a different mission for The Dude — to find his missing trophy wife, Bunny. Against orders, The Dude enlists the help of his bowling buddies, rageaholic Walter and dimwitted Donny. From there, the plot twists and coils in on itself like a riled-up rattlesnake. Aside from the richly bizarre characters and the labyrinth of red herrings, one of the best things about this comedy is how it demands multiple viewings to fully appreciate it. You’ll know you’ve watched it enough times when you can have an entire conversation just using quotes from the film.
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