When we wrote our article highlighting some of the best Western Movies of all time recently, it didn’t feel like a terribly controversial list. We know we left off some favorites (Bone Tomahawk, etc.), but maybe the Western genre just doesn’t have quite the massive following or number of films released each year that would make the task too hard to complete. So, we thought we would take things up a notch and try to tackle creating a list of all-time great Comedy Movies. There’s no way we can create a list that would make everyone happy, but let’s see how our favorites stack up with yours.
Groundrules
For the sake of cutting down the list of movies to consider, we’re going to focus on comedies from 1970 through the present day. Still a huge span of over 50 years, so we feel pretty good about the time span. This is a list of movies and not series or stand-up comedy specials. So, don’t look for the latest Aziz Ansari special on Netflix. We’re also not listing these in any particular order. So, we’re not claiming any of them as the single best comedy on the list. That gives us a bit of flexibility.
We’re looking for comedies that stand the test of time. We’ve all seen a comedy that was hilarious the first time we saw it, but then a few years go by and in rewatching it, we wonder what was so funny. We think these movies all hold up across the years - or will hold up, for the newer movies on the list.
One last quick note. This was a very difficult list to create. First off, it was surprisingly hard to put the label of ‘all-time best’ or at least ‘best of the last 50 years’ onto more than a few obvious choices. After that it got very tricky. We know we left a bunch out that people love. But, let’s dive in.
The List
Caddyshack (1980)
A true comedy classic from the 1980s. Filled with talented actors and comedians like Bill Murray, Chevy Chase, Rodney Dangerfield, and Ted Knight this will make a lot of Gen-X lists of great comedies. When you learn more about how the movie was made, it just adds to it’s almost mythical standing. Filled with memorable quotes (So, I got that going for me, which is nice - You’ll get nothing and like it - He’s a Cinderella story…) and memorable scenes, this story of a few days on a country club golf course is ridiculous and utterly memorable. No question it belongs on the list.
The Hangover (2009)
When this somewhat under the radar movie hit theaters, expectations weren’t likely that it was going to be up for consideration among the funniest movies of all time. To be fair, the brand of comedy isn’t for everyone, but if it’s your cup of tea, it was an instant classic. Featuring a bunch of underrated actors, (Bradley Cooper, Ed Helms, Zach Galifianakis) the movie shows the aftermath of a memorable (or actually incredibly forgettable) bachelor party in Las Vegas. It remains one of the funnies movie theater experiences I have ever had. I and many people were quite literally crying, we were laughing so hard. It is a bit of a guy’s movie, as my wife enjoyed it, but not quite to the extent that I did.
The 40-Year-Old Virgin (2005)
Here’s another on that may appeal a bit more to guys, but it still easily makes our list. Starring Steve Carrel, Paul Rudd, Seth Rogan, Romany Malco, and Catherine Keener, it somehow manages to be incredibly over-the-top offensive and yet kind of heart-warming at the same time. It’s also the movie that took Carrel’s career to a whole new level, while also being a launching pad for Rudd and Rogen. Such a talented cast in a story of a middle-aged guy who has never been in a physical relationship before. It was another laugh-out-loud in the theater experience.
There’s Something About Mary (1998)
One of a number of hilarious movies from the Farelly brothers (the directors) this completely insane take on the romantic comedy featured Ben Stiller, Matt Dillon, Cameron Diaz, Chris Elliott, and a host of other supporting actors. The story of unrequited, long-term love and how every guy in the movie eventually falls for Diaz’s Mary is just fantastic. Stiller is steller as the poor everyman who experiences the most embarrassing and hilarious injury as a teenager taking Mary out on a first date and then spends the next couple of decades pining for her. Matt Dillon is also incredible, giving a memorable comedic performance. You’ll never look at hair gel the same way again.
Anchorman: The Legend of Ron Burgandy (2004)
You couldn’t have al ist of great comedies from this time period and not end up with at least one Will Ferrell gem in the mix. We had plenty to choose from, but landed on Anchorman. It also gets the boost from starring Christina Applegate, Steve Carell, Paul Rudd, and David Koechner as part of the news crew. Still, Ferrell is the heart and sould of this ridiculous comedy about San Diego anchorman in the 1970s. It’s over-the-top and not exactly family-friendly, but it is quintessential Ferrell and not to be missed. Stay classy San Diego!
Groundhog Day (1993)
Another Bill Murray classic, this one was filmed not far from where I grew up, so it has some added personal meaning for me. It’s also the sweetest movie on the list, telling the story of how a fairly awful person (main character, weatherman Phil Connors played by Murray) finds redemption by experiencing an untold number of years replaying the same day, over and over. The movie is really Murray’s spotlight, but he shares it with a solid cast, including Andie MacDowell, Chris Elliott, and Brian Doyle-Murray, among others. It absolutely gets some points for being heartwarming, but never loses sight of the comedy of the situation. This one is also pretty family-friendly, giving it a wider audience than a few of the movies on our list.
This is Spinal Tap (1984)
The mockumentary is a fairly established comedy sub-genre by now, but in 1984 it was still very novel and Spinal Tap stepped in and turned the volume up to 11. This Rob Reiner film follows the career of aging metal band Spinal Tap, with Michael McKean, Christopher Guest, and Harry Shearer taking on the key roles. It’s stupid, nonsensical, and completely hilarious in how it both skewers the music industry, while getting viewers to love this ridiculously awful band. In fact, fans took to it so much that the group actually performed live and recorded music as Spinal Tap over the years.
Monty Python and the Holy Grail (1975)
Monty Python has it’s own special place in comedy royalty, but this film is the one that stands out as the epitome of the comedy group’s talents and absurdist take on the Aurthurian legend. The Pythons (Graham Chapman, John Cleese, Terry Gilliam, and Terry Jones) give us a ludicrous take on the Middle Ages, complete with a Black Knight that thinks losing a limb is a flesh wound, a goup of knights in need of shrubbery, a murderous rabbit, and a castle full of rude Frenchmen. A comey classic in every sense of the word.
Ted (2012)
What to make of a romatic comedy that includes a foul-mouthed, pot-smoking, talking stuffed Teddy bear? A lot of laughter, that’s what. This Seth MacFarlane film stars Mark Whalberg and Mila Kunis, along with MacFarlane as the title character. It is irreverent, stupid, nonsensical, offensive, and so, so funny. It’s a rare one that doesn’t have many movies to compare with. It’s a coming of age story told amidst some of the most ridiculous scenes you can imagine.
What we do in the Shadows (2014)
One more mockumentary for this list, but a much more recent version, with this New Zealand sendup of both vampire movies and the whole Office-style documentary/comedy. It also launched the career of Taika Waititi (now of Marvel movie fame). Imagine what life would be like for vampires living in the modern world. That’s the simple premise that fuels this wonderfully funny flick, that has now been turned into an equally funny TV series.
