Jordan Peele once remarked that both horror and comedy find a bond in grounding absurdity. The more real your world is with your absurd notion, the scarier it is. Groundhog Day is a good example of this. Take the comedy out and your are left with a nightmare scenario- being stuck in a time loop. Dr. Strangelove is simultaneously one of the bleakest films on this list and one of the funniest. When researching/preparing for the film, Kubrick noted that the only direction to take a notion so absurd- nuclear oblivion- is the comedy route.
Horror and comedy make for the two genres hardest to master. Everyone thinks they can make them, leading to a glut of shit in both genres. Even less succesful formulas have been concocted for horror comedies.
This leads to how I, or anyone of you, construct their lists of favorite comedies. Taking a cue from Bennett Media, these are strictly made for laughs.
1. The Big Lebowski (1998)
Rewatchability is one of the key factors in any movie that makes this list. The thing about Lebowski is that it only gets funnier the more I watch it. Every actor from lead to minor role is on point here.
2. Beetlejuice (1988)
It fit like a glove when I first saw it. I had seen Batman before it and Tim's style was something I was way into.
3. Midnight Run (1988)
A film that jumps higher and higher on my list of favorites each time I watch it. It's now secure in my top 100.
There's not a single character or side character that doesn't have a memorable line or hilarious comic timing.
4. Sherlock Jr. (1924)
Are you a Chaplin guy or a Buster guy? The Tramp or Stoneface? I've always had a soft spot for Keaton. This, his 1924 effort is bursting with ideas and inventiveness. I still scratch my head in disbelief in how he accomplished the stunts in this movie.
5. Dr. Strangelove (1964)
When faced with the question, who do you think gave the funniest performance in a film?" my answer would be Peter Sellers' three performances here.
6. Female Trouble (1974)
My heart belongs to John Waters. His early stuff will always outshine his later stuff. Divine is a major reason why. The Dreamlanders are all here in top form.
7. The Burbs (1989)
It was a family tradition that on vacations, The Burbs and Jaws were always taken to watch. The van had a TV between the driver and passenger seats for me and my brother to watch stuff while on long trips. As such, this movie has been instilled into my DNA.
A dream cast (Tom Hanks, Carrie Fisher, Rick Ducommon, Bruce Dern, Corey Feldman, Henry Gibson, Dick Miller), one of my favorite Goldsmith scores, and a script that lets everyone shine.
8. Fear and Loathing In Las Vegas (1998)
Reading the book recently made this sneak into my Top 100. Thompson's voice is channeled through Gilliam's visuals and Depp's performance. And Del Toro gives a comedic performance for the ages.
9. Ed Wood (1994)
Burton's best directed effort. There's only a handful of biopics that are as good as this one. Beyond the camerawork, Depp and Murray give two of their funniest performances. I only see this movie going higher on the list.
10. A Serious Man (2009)
Receive with simplicity everything that happens to you.
After the dire seriousness of No Country, the Coens wisely pulled a one-two punch of comedy. This one, imbued with an autobiographical nature, manages to be their best comedy since Lebowski. Whereas Burn After Reading was littered with big names, A Serious Man introduced us to fresh faces: Michael Stuhlbarg, Richard Kind and Fred Melamed.
11. This Is Spinal Tap (1984)
Shit sandwich this is not. The 80s can be summed up in a word: excess. 80s hair metal in particular. Spinal Tap managed to send up the scene so accurately that several bands have asked the makers if it was based on them.
12. After Hours (1985)
Scorsese does Kafka. The absurdist comedy here is delivered by a director having genuine fun.
13. Ferris Buller's Day Off (1986)
My cousin introduced me to this as his favorite movie. Being set in Chicago and giving full breadth to the city is a major plus.
John Hughes movies became a touchstone after this. The way he depicted teenagers, with all their flaws and all. One of my favorite commentaries is from Hughes on the DVD release.
14. Dazed and Confused (1993)
Everytime I watch it I feel like I'm hanging out with old friends. The mark of any great hang out movie.
15. Young Frankenstein (1974)
Of the Brooks movies, Franky is the one I saw first. Blazing Saddles followed. When considering which is better, it's simply down to personal taste. Both are laugh out loud funny. But I will take Cloris Leachman over Madeline Kahn and Peter Boyle over Cleavon Little.
16. Monty Python and the Holy Grail (1975)
Stands toe to toe with Flying Circus. Top 3 Gilliam.
17. His Girl Friday (1940)
In the 40's, two genres reigned supreme- film noir and screwball comedies. The latter had Ernst Lubitsch and Preston Sturges firing on all cylinders. Howard Hawks, never one to be shy from tipping his toe in just about every genre out there, crafted a movie faster than any of them.
18. Play It Again, Sam (1972)
My favorite Woody. What about Friday night?
19. Some Like It Hot (1959)
You won't find another director more at the top of his game than Wilder between 1950 and 1960. He began the decade with the haunting Sunset Boulevard and closed it out with Some Like It Hot. Talk about range!
20. Modern Romance (1981)
I could have went with Defending Your Life or Lost In America, Modern Romance just sticks with me longer than the other two have. Comedy and heartbreak go hand in hand with sly visual gags.
21. Airplane! (1980)
A film so packed with gags that it's nearly impossible for all of them to land on the first run. Airplane gave us two actors from the Golden Age of Hollywood stretching their comedic chops- Lloyd Bridges and Leslie Neilsen.
22. Groundhog Day (1993)
Another movie nearly memorized word for word. Groundhog Day has been a tradition in my house in the same way The Burbs and Jaws were. Phil Conners might be my favorite Murray performance.
23. Rushmore (1998)
Barely edges out Tenenbaums as my favorite of Wes. He's found a style and stuck with it throughout his whole career. This isn't exactly a bad thing. You know it's an Anderson picture just by the way he frames shots. Is he going out of his comfort zone? No. Which is why he'll always be a director I like but not a director I love. Having said that, he managed to craft a handful of films that hit the funny bone in just the right places.
24. Napoleon Dynamite (2004)
The comedy is here is so specifically tailored to a character type that when it came out, people either found it brilliant or annoying. I am happily of the former camp.
25. Raising Arizona (1987)
There's a short, short list of actors who have an ability to go from a character like H.I. McDunnough to Ben Sanderson to Charlie/Donald Kaufman to Terence McDonagh to, most recently, Chef Robin Fell. H.I. might be my favorite character he's portrayed.
Besides Gremlins 2, it's the only live action movie that channels the zany anarchy of Looney Tunes.
26. The General (1927)
The first Keaton I saw. Clever, innovative and incredibly athletic, Keaton turns cause and effect physics into poetry. As with Sherlock Jr., this film just does not slow down for a break.
27. Hot Fuzz (2007)
It's always rotating between this and Shaun of the Dead as to what I find the funniest.
28. Bad Santa (2003)
As endlessly quotable this movie can be, the scene between John Ritter and Bernie Mac catapults this into a classic for comedic timing.
29. The Money Pit (1986)
You can draw a straight line from Tom Hanks to Buster Keaton in the 'chain reaction of destruction' scene.
Seriously, go watch this movie or...I'll not like you anymore.
30. Love and Death (1975)
Like John Waters, Allen surrounds himself with what he loves- Bergman, Russian literature, and enough neurosis to make Larry David look normal.
31. Wet Hot American Summer (2001)
Given that it's directed by David Wain, a handful of actors from the State (Michael Ian Black, Michael Showalter, Ken Marino, Joe Lo Truglio) make their appearance. Along with the likes of Paul Rudd, Will Forte, Amy Poehler and Elizabeth Banks. Though for my money, Christopher Meloni, an actor who was in the grim prison drama Oz at the time, nearly steals the show from all of them.
32. Ghostbusters (1984)
I watched it at just the right moment in my life. I was in a huge Burton phase and sought out stuff that used some of the same ingredients. What is so striking here is the casting: Murray, Aykroyd, Ramis, Weaver, Moranis, Hudson, Atherton. Each actor would take on a role in a movie or TV show (Oz in Hudson's case) that I would come to love. They are all here, playing brilliantly off of one another.
33. Popstar: Never Stop Never Stopping (2016)
It's the funniest movie to come out of the 10's. And I can say that with full confidence. It's our generation's answer to Spinal Tap.
34. Serial Mom (1994)
Waters always filled his movies with the stuff that interests him. And what stuff that is! Herschell Gordon Lewis, Chesty Morgan, and a homicidal mother played to perfection by Kathleen Turner.
35. In the Loop (2009)
Politics has been a bought and paid game since the 70s. Any commentary worth anything should approach the subject with sharpened knives. The satires that make this list all have to do with communication breaking down between people. Thus leading to dire consequences for all involved.
The insults here are top tier.
36. Addams Family Values (1993)
A sequel better than the original for several reasons. The bizarro summer camp, the hi jinks with the new baby. For my money though, the greatest addition is a simply better villain in Joan Cusack, who delivers a knock out performance as Debbie Jelinski. Graceful, delicate.
37. Sullivan's Travels (1941)
There's an umbilical cord connection from Preston Sturges to the Coen Brothers. I came to Sturges after trying to get my hands on every interview the Coens made. I kept seeing his name pop up as a main influence. Like the Coens, Sturges' dialogue pops off the page. It was witty yet had unique literacy. There's a playfulness with language that I immediately respond to. Sullivan's Travels is a key example of this.
38. The Naked Gun (1988)
I'm a fan of all three movies. Though if I were to make a list of funniest scenes from all three, the bulk of them would be found in the first one.
39. Mystery Science Theater 3000: The Movie (1996)
MST3K never really had a bad season. It was always about the movies they were riffing. This Island Earth offers plenty of opportunities for Tom, Crowe and Mike to hit their stride.
40. The Cable Guy (1996)
Like What About Bob?, the hanger-on is played by a comedian. Also like Bob, the movie can shift into horror territory at the drop of a dime. They just choose not to. What's so enjoyable about these types of movies is watching the two leads walk a tightrope between the two genres.
41. Best In Show (2000)
It only took two movies together to perfect their chemistry. The Guest stable of comedians don't quite top the heights they reach here. Considering the absurdity of the subject matter they tackle, it would be hard to.
42. National Lampoon's Christmas Vacation (1989)
A Christmas Story, It's A Wonderful Life, Home Alone and this movie are all traditions at Christmas time. Always have been. The Vacation series is at best, uneven. A solid first entry, a lackluster European installment, a great third film and a middling trip to Vegas. All the anxiety of family get togethers, finding a good tree, shopping, etc. is pictured here. Complete with a pitch perfect Julia Luis Dreyfus as the neighbor.
43. Observe and Report (2009)
A comedy version of Taxi Driver is the best description I've seen of this movie. It's the movie that introduced me to Jody Hill.
44. A Fish Called Wanda (1988)
John Cleese and Michael Palin are worth the price of admission. But it's Kevin Kline's character of Otto who makes the film take off into astronomical comedic heights.
45. Four Lions (2010)
First you laugh, then you take a second to think about what you are laughing at, and before you know it, a bird was just blown up before your eyes. British satirist Chris Morris made waves with his show Brass Eye. A show that fearlessly took on controversial subjects. Four Lions continues this fearlessness.
46. Bad Trip (2021)
Eric Andre represents the next logical step of anarchy in comedy. Tim and Eric keyed into the anti-humor scene. Andre jumped head first into it. The best road trip comedy in years.
47. Wayne's World 2 (1993)
Wayne Campbell will always be what I remember Mike Myers for. Between the two movies, part 2 is the funnier one.
48. What We Do In the Shadows (2013)
Vampire movies have all but had the life sucked (pun intended) out of them. No, it's not only because of Twilight. Like the zombie genre, the tropes have become tired. Taika's mockumentary hits at just the right time.
49. Tommy Boy (1994)
A road movie with two comedians whose chemistry rivals Martin and Candy. Beyond their performances, Rob Lowe is at his peak here.
50. Office Space (1999)
I never got into Beavis and Butthead. Nor did I obsessively track Judge's work following this. This somehow just works for me. It nails the tediousness of bosses, and strange co-workers.
