Funny how?

Comedy is funny...
Funny how seriously we take it, how defensive we get, how subjective it is.
And it ain't just about movies; a 'sense of humor' is only that - no one knows what it means.
So, there, that should cover my ass from any mindless debate (though a little constructive nudging is manageable).

A lotta thought & science went into this - of course, those of you who categorize and catalogue your interests as scrupulously as I can understand how breezy it was to compile such a straightforward list.
And it is very much that: straightforward.
My criteria included staying true to the genre; there are tons of funny movies that I don't call 'comedies,' either because they're too dark (Pulp Fiction, American Psycho), too heavy (...And Justice For All, The Fisher King), too incidental (Plan 9 From Outer Space, The Room), or just belong in another genre entirely (Running Scared, Back to the Future).

My other highly scientific stipulation is that actual, physical laughs are the prevalent takeaway. There's plenty of excellent lighthearted cinema that's expertly crafted but lacking in lolz. Much in the same way a lot (or most) of the best horror isn't actually scary -- and that's why this isn't "best" comedies or "favorite" comedies, but "funniest."

Which brings me to my last overly analytical observation. Taking a step back to guarantee honesty to myself and to you, this list is an obvious testament to the evolution (and sometimes devolution) of what's funny from generation to generation. It's strictly for the purposes of statistical curiosity that I point out the absence of Chaplin, The Marx Brothers, and Neil Simon, as well as Apatow, Stiller, and Edgar Wright - which helps to reiterate that very idea of how dated, divisive, and personal "funny" is... I think there's less than 50 years of celluloid on my own list.

And without getting into the 'purpose' of listing for the umpteenth time, I would like to say: like a badge of recognition, these little structured assortments of pop culture are unique within themselves (what they're about, the order they're in) and also, more importantly, from person to person. Any list I've composed has obviously been exclusive to my own taste, but this one in particular feels the loudest and the proudest - that is, to say, the most obvious. Anyone who knows me can read it and think, "Well... that figures."
And if you don't know me by now, you will never, never, never know me.
No you won't!

- Paul

50) Dumb and Dumber (1995)

It took years of growth and blossoming maturity to appreciate this gem - less for what it is, and more for what it isn't. In between the abrasive punchlines and gross out slapstick is a wealth of subtle nuance - courtesy of the comic genius of its two leads.

49) Kids In The Hall: Brain Candy (1996)

Just about most sketch comedy can't make the leap to narrative feature - even this one struggles to secure a cohesive thread.
Still though, the not-weird-enough premise does allow the 'Kids' plenty of opportunities to dress up & play some new (and some of their best) characters.

48) The Royal Tenenbaums (2001)

Whatever problems I've had with the gentleman, young Wes certainly has the market cornered on dry humor. And that dryness always works best when it's laced with some doses of hijinks and personality - in this case, due largely to the stellar cast -- particularly one Gene Hackman. Not only does he steal the show, but everyone else's best scenes are the ones where they have to go up against him.

47) Caddyshack (1980)

Apart from its tedious teen subplots and lame gopher puppet, it might've been a little flawless.
Populated with some of the best comedians of a generation, each at the height of their game and each with their own unique brand of comic timing, they bounce in and out of absurd situations, existential monologues, and cutting observations.
Which is nice.

46) Like Father, Like Son (1987)

I wanna use this as an opportunity to talk about the creative team of director Rod Daniel and composer Miles Goodman. Like Burton and Elfman, they manage to compliment each other's talents, resulting in a very stylish, sinister-yet-whimsical tone that elevates otherwise lowbrow fare (they'd achieved a similar effect with Teen Wolf in '85) to a unique level of visceral comedy/horror. It makes it that much funnier.

45) Greedy (1994)

The blueprint is refreshingly old fashioned: a huge cast of A- and B-list character actors stuck together in one location, firing crisp dialogue at one another. That & the continually unfolding plot would make for an excellent stage adaptation (and I actually mean that in a good way).

44) The Birdcage (1996)

Not one of Mike Nichols' greatest visual achievements, but it's less about that and more about drag, dinner, and John Wayne.
I won't compare it to the stage play or the original adaptation because I've not seen them - but I'm confident in my assessment that Nathan Lane's performance is now the stuff of comedy legend. And I'll always be a fan of Hank Azaria's flaming Guatemalan accent.

43) Wayne's World 2 (1993)

It's not easy choosing between the two, but the sequel always felt weirder, sillier, and so: funnier.
I've talked about Ralph Brown's bizarro performance as psychotic roadie Del Preston before, and how he stole the movie - so I'll use this space to call attention to one of the greatest fight scenes ever put on film: Wayne vs. Jeff (James Hong) in a bravura spectacle of hand-to-hand Kung Fu and English-language dubbing.

42) National Lampoon's Christmas Vacation (1989)

The best of the Vacation movies (which isn't a huge accomplishment), it not only nails most of the jokes it goes after (no matter how over-the-top), but it also manages to capture the spirit of the holiday - which is even harder to do.
It's so intensely quotable that you can bang out lines year 'round - in and out of season.

41) The Blues Brothers (1980)

The closest we've ever come to Saturday Night Live: The Movie -- and the brilliance of it is that all of its sketches, guest stars, and musical performances blend into one cohesive storyline.
And who knew car chases could be so hilarious?

40) Death Becomes Her (1992)

The idea of a few overpaid actors hamming it up for an effects-driven storyline doesn't sound all that appealing. But thanks to more-than-competent effects, an okay script, some adventurous direction from Bob Zemeckis, and probably Bruce Willis' best performance, it comes through as an oft-overlooked masterwork of shenanigans.

39) The King of Comedy (1982)

It's weird (probably only to me) that this is the only Jerry Lewis movie to make my list -- and that the funniest (and scariest) performance belongs to DeNiro. But, it is and it does.

38) Airplane! (1980)

Neither overrated nor underrated; too many great characters to have a favorite, too many lines to even mention, and (most of) the humor has proven to be timeless as the yuks still hold up. Golly!

37) Best In Show (2000)

The best of Guest, IMO.
The great thing is that it's already a funny movie for the first two thirds, and then Fred Willard swoops in and levitates the whole thing to astronomical heights.

36) Office Space (1999)

Who'd a thunk - the creator of Beavis and Butt-Head would be a true master of subtle humor (not that it's not without its broadness).
No one isn't notable, but extra nods to Stephen Root, Gary Cole, and John C. McGinley.

35) Tommy Boy (1995)

It's the only truly great Chris Farley movie, as the ones that followed couldn't match its charm (even if it was a rehash of Plains, Trains, and Automobiles).

34) Mystery Science Theater 3000: The Movie (1996)

Probably the smoothest transition from screen to screen that's ever been achieved.
Fans say it all the time, and it's true: had it just been an episode of the TV show, it'd be one of the best (either in a movie theater, or in normal view!).

33) Mother (1996)

The only Albert Brooks movie to chart - which says a lot for this particular movie. He's top-notch as usual, but anyone unfamiliar with the brilliance of Debbie Reynolds needs to familiarize themselves via this particular performance. Awards shoulda been won.

32) High Anxiety (1977)

If you know Mel, you know this one. And if you know Hitchcock, you'd better know this one.
It's responsible for sparking my crazy adoration of Cloris Leachman.

31) The Naked Gun: From the Files of Police Squad! (1988)

The entire trilogy is on the ball, but there's a healthy serving of childhood nostalgia with this one. That + the entire final sequence in Anaheim Stadium is the best part of all of 'em.

30) Trading Places (1983)

The whole 'New Year's Eve on the train' thing feels like a different movie (of lesser quality), but everything else is the kinda funny I grew up on. And it covers three major holidays, so there's plenty of time to watch it!

29) Napoleon Dynamite (2004)

Now that the initial shock of originality has long passed, one can look at it with fresh eyes and truly appreciate that - after years of rip-offs and cult status - it truly is comic genius on its own flippin' sweet level.

28) Ferris Bueller's Day Off (1986)

It's hard to imagine how dumb or irritating it could've been had it not been in the hands of so many talented people. And for all its great scenes and perfect lines, its most admirable (and funniest) attributes are how it depicts school, and the intuitive understanding of that feeling of 'time off.'

27) Stripes (1981)

There's more Bill Murray on this list than anything else (which should be a tip-off), and for whatever greatness he gives in all these other flicks, Stripes clearly allowed him more freedom and screen time than he'd ever had - before or since. And it pays off.

26) A League of Their Own (1992)

When something's this sweet and optimistic, it puts you in a mood that just makes the laughs flow that much easier.
Also, Tom Hanks' funniest role...? I think maybe, yes.

25) Raising Arizona (1987)

Live action Looney Tunes mixed with existential dread: that describes the Coens, sure, but they (nor anyone else) have ever mixed highbrow this high and lowbrow this low.
Also, Nic Cage's best performance...? I think maybe, yes.

24) Easy Money (1983)

This is a very particular brand of humor: 80s New York macho wiseguy humor. In other words, if Rodney Dangerfield were a movie...
And if that doesn't sound like your mug of beer, it's just as worth it for Joe Pesci and Taylor Negron.

23) Groundhog Day (1993)

Another premise that could've easily gone off the rails had it not been done right. But alas, it became a new standard of comedy - largely, I say, due to its perfectly paced (not to mention highly original) script.
Like a handful of these movies, the funniest ideas come outta the scariest ones.

22) A Fish Called Wanda (1988)

It could've been about anything -- this is a movie that rests entirely on its performances.
And while Kevin Kline gets most of the notice, it's worth it to give extra attention to two Python vets and an actress who once effortlessly held her own against Dan Akyroyd and Eddie Murphy.

21) My Cousin Vinny (1992)

One of the few on here in which an engrossing story actually drives the laughs: long dialogue scenes, fish outta water stuff, and repetition through (pun) trial and error.
Even with an Oscar win, it's still not as revered as it should be.

20) Monty Python and the Holy Grail (1975)

Way way better than their other films, and nearly better than Flying Circus -- which could make this the ultimate Monty Python experience.
Probably the most genius thing about it will always be that, if you took away the humor, it could stand on its own as the grittiest, spookiest, best depiction of the Middle Ages... with or without actual horses...

19) Young Frankenstein (1974)

Mel Brooks' best by a mile and a half. And how could it not be? - it's most likely the funniest ensemble of actors ever assembled.
I memorized every line and sound effect at the age of 4, and performed the entire movie for my parents, a cappella.

18) Throw Momma From the Train (1987)

Danny DeVito depicts slapstick with dramatic choreography and a dark brutality that hits me at just the right angle.
I can remember: even days after seeing it for the first time, I'd be in school and think of moments and have to suppress laughter.

17) What About Bob? (1991)

I'm always gonna be a sucker for the straight man/funnyman dynamic, and this is one for the (modern) ages. And while there's a clear line between who's who, it's hilarious enough that sometimes it's hard to choose which lead is funnier.

16) A Serious Man (2009)

Right when I thought the Coen Bros. had dried up a bit, they snuck this card off the bottom of the deck: as sharp and darkly funny as their Barton Fink days, but with some added confidence in their now-famous quotable one-liners and catchphrases.

15) The Money Pit (1986)

Humor via destruction -- but that's just part of it.
The stunts are sometimes so elaborate that you can't help but laugh (even if it's sometimes out of amazement), but when you've seen this (or any of these movies) as many times as I have, it's the dialogue that dominates the foreground, and nearly every line becomes part of my own personal rhetoric.
And 80s Tom Hanks.

14) The 'Burbs (1989)

Another one on the list with a single location and a fixed amount of players - with nothing but their dialogue to guide them through satirizing the mystery genre, the horror genre, and the white American suburbs.

80s Tom hanks.

13) Fear and Loathing in Las Vegas (1998)

It's not always easy to translate humor from literature to film - luckily everyone got it right (mostly by staying true to the original words).
While Johnny gets his praise for his dead-on Hunter Thompson impression, Benicio del Toro's Dr. Gonzo is a concoction of ferocious physical comedy worthy of Curly, Belushi, and Chris Farley, and needs more recognition.

12) Arthur (1981)

It's fun to watch others have fun, and who has more fun than a drunken millionaire?
Laughter is infectious, and who has a better laugh than Dudley Moore?
Is that all there is to it? It is a blissfuly simplified fable, and that's part of its charm. But while I assert that most of these movies are "quotable," this movie certainly lands in the Top 3.

11) Uncle Buck (1989)

A Candy-Hughes collaboration is something we're stuck with far too little of, so every frame is precious.
When a character is (obviously) written for a specific actor, the desired outcome is usually spot-on - as is the case with Buck Russell, who may as well join the ranks alongside The Tramp, Inspector Clouseau, Ace Ventura, and Beetlejuice.

10) Beetlejuice (1988)

Outside of the crazy over-the-top performances and morbid sight gags, the best joke of this whole movie is that, at any given moment, you can't believe this made it into the mainstream.
Maybe the greatest ending of any kinda movie: Winona Ryder levitating over the ghosts of nameless football players, dancing and lip-syncing to Harry Belafonte. That's comicality you can't put a label on.

9) Sleeper (1973)

Absurdity at its purest, Woody at his best.
People divide his stuff up into "funny" and "non-funny." But for the first half of the 1970s, he was on a whole other plane: "screwball" - and Sleeper was the pinnacle.
The opening electric wheelchair scene is still too much for me to take.

8) I Love You to Death (1990)

Pace changes are my favorite (we'll get into more of than soon) and nothing lends itself to buffoonery like true crime.
A story with a gut-wrenching premise (partly because it's true) very slowly (and believably) unravels into sitcom-worthy hijinks, and never do we feel bad for laughing.

7) The In-Laws (1979)

Here's a recipe for hilarity: both straight men acting erratically, or, the comic relief maintaining composure... Which is which? Depends on what scene we're at.
Arkin and Falk: a comedy team we didn't know we needed until we got it - and, man, am I forever grateful for it.

6) Ed Wood (1994)

Biopics generally stink - mostly because I use this movie as the metric.
It's easy to laugh at self-delusion and blind optimism, but that proves to be only one fraction of the movie. Some great writing allows all these eccentric characters to have their own voice in their own moments, and it's certainly not unfair to marvel at Johnny Depp's bizarre translation of the real-life Ed Wood, Jr.

5) Plains, Trains, and Automobiles (1987)

The 'road trip' movie would never be the same. Neither would the 'buddy picture,' the 'dramedy,' or my own Thanksgiving holiday.
John Hughes' best, it incorporates all-sorts: slapstick, deadpan, prop comedy, one-liners (sometimes set to music)... all with a heart and a lesson, like he knew how to do so well.

4) Play It Again, Sam (1972)

My favorite Woody Allen movie not directed by Woody Allen.
It's so rich and well-paced that you'd hardly guess it derives from Broadway -- but because it was initially a play, the entire structure rests squarely on Woody's anecdotal punchlines and physical comedy, and they were never better.

3) Dr. Strangelove or: How I Learned to Stop Worrying and Love the Bomb (1964)

Satire is basically never done correctly. In fact, in my own mind, I equate the word itself to this one and only institution of jet-black humor - a movie that can only be classified as 'comedy,' courtesy of a filmmaker whose sense of humor I've always shared.
No one doesn't give a funny performance, but my favorite bits are the ones between Peter Sellers and Sterling Hayden: another unlikely comedy team that could've had their own movie to play with.

2) Midnight Run (1988)

One of the funniest scripts ever written is a good place to start.
I could call it an action movie - until I make the assessment that the entire movie is lacking a comic relief: thereby, everyone's a comedian! (Even imposing guys like Yaphet Koto and Dennis Farina get some of the funniest lines.)
All of these movies have a handful of famously funny scenes; watching Midnight Run, every scene feels like that scene.

1) Ghostbusters (1984)

It's the same concept as Strangelove: the funniest thing in the world just may be the end of it. And therein lies the nexus of my own sense of humor: to point and laugh at the face of danger, all the while in the face of danger.
I've always thought of it as an efficient and effective horror movie, and that + the attention to detail, the seriousness of (most) of the monsters, and the weight of the plot only added fuel to the funny. Because, in reality, when the real-life apocalypse hits, it'll be just as dumb and confusing as a 100-foot marshmallow man.