Let’s face it, there’s a lot of comedy movies out there these days. In fact, throughout the history of cinema, comedies have been a oft-used staple of the silver screen. It’s even been proven that as far back as the written word people have been making comedies for people to either laugh at, or dismiss entirely. Wouldn’t you believe it, with many of these films to choose from, people have taken to ranking these available titles as a way to describe what they think is the best one. Sometimes you’ll see people just throw out a handful of comedies as a way of showing their taste in these films, other times people will put together a comprehensive list of their favorites from as many as 5 to 10 movies of which they rank the best.

I, of course, could never limit the limitless to just a mere 10 movies. No. So, over the course of one weekend I complied a list of 500 comedy movies that I deemed worthy of my ultimate list. I then ranked them in order in which I enjoy them most. I couldn’t believe I was able to trim down what is probably over 1,000,000,000 comedy movies that have been crafted all time into a paltry 500, either, but here we are.

That said, I don’t have the hubris to assume that you’re interested in hitting the next button on this website a bunch of time to get my complete list, nor do I have the money to pay for the webspace to host it. Therefore, I’ve decided to present to you an except from my master list of favored funny movies.

In this case, we will be taking a look at my selections #286 through #277:

#286. Weekend at Bernie’s II

We’ll be seeing Weekend At Bernie’s Part One later on in this list, but the second film deserves mention as well as it takes the situational comedy from the first film and turns it up to 11 (to quote a film that may or may not be in this list as well). Bernie is still dead and by golly, after 4 years, no one is the wiser! I mean, you would think by now the film would tackle such harrowing subjects of grief or maybe even tactfully handle the situation of decomposition, but no, it’s just one conga line after another to hide the fact that Bernie is a marionette for two douches who were trying desperately to claw themselves out of the 80s. And you know what? It’s a gas.

Most hilarious quote:

Richard Parker: What kind of idiots would steal a dead body?
Larry Wilson: We did!
Richard Parker: (almost inaudible and seemingly out-of-character) I want to die.

#285. Caddyshack

I bet you thought this classic would be higher on the list, didn’t you? From an all star cast in the height of great comedies from the 1980s and with a plethora of quotes and scenes that even the best comedies after it could only dream of aspiring to, Caddyshack is a comedy clinic. Surely #285 is too low for such a great film. Well it would be higher, if not for my crippling fear of sassy gophers.

Most hilarious quote:

Spalding Smails: Doodie!

#284. Confessions of a Shopaholic

Wow. I know I am kind of blazing a trail on this one but, to me, it has all of the makings of a true cult classic. Sure it came out recently, and everyone hated it, but that’s the same thing you could have said about Duck Soup when it came out way back in 1938. Just like the Marx Brothers before them, Sophie Kinsella and Isla Fisher have really struck a chord that resonates at a frequency that you may not hear at first with your finely tuned comedy ears but as it sits with you over the years, and with repeated viewings, I’m willing to bet the laughs will be deafening before you know it.

Most hilarious quote:

Rebecca Bloomwood: You speak Prada?

#283. Idiocracy

You had to expect a Mike Judge movie would show up at some point! (And don’t worry, you’ll see him listed again as the list progresses. A little hint, Extract was a clever little film.) Unlike Confessions of a Shopaholic this was a film that just shot out of a cannon as one of those movies you couldn’t get away from and didn’t mind anyway because it was such a funny fucking movie. I mean, how many President Camacho’s did you have at your office Halloween party? I know at my office there were several at the very least. I would likely rank this movie higher but it became one of those films that was just so over-commercialized that you ultimately get sick of it. It’s still worth a laugh or two if you’re one of the two or three people left who hasn’t seen it.

Most hilarious quote:

Pvt. Joe Bowers: [addressing Congress] There was a time when reading wasn’t just for fags. And neither was writing. People wrote books and movies. Movies with stories, that made you care about whose ass it was and why it was farting. And I believe that time can come again!

#282. Class Act

I would be remiss if I created a list of comedies that did not include a Kid ‘N Play classic. This Dickensian-esque tale is a relic of the early 1990s and should be taken out at least once per year to be examined, enjoyed, and preserved in memory. A prince and pauper plot is held together with the goodhearted, well-meaning raps of the titular characters and a little mix of Pauly Shore. I would wager nothing else in pop culture quite expresses what it was like to be alive in 1992 than Class Act.

Most hilarious quote:

Duncan’s Dad: Honey, have you ever wondered about our son’s sexual preference?
Duncan’s Mom: I didn’t know he had one!
[they start laughing together]

#281. City Slickers II: The Legend of Curly’s Gold

I thought long and hard about the decision to include City Slickers or City Slickers II and I’ll be frank, the subtitle The Legend of Curly’s Gold went a long way to swaying my decision. So, while you scan the next 200 or so movies on my list, keep in mind that you won’t find the original movie which means no awesome Bruno Kirby baseball quotes about who played third base for…Pittsburgh in..1960. That’s okay though, because the Curly of whom has a legend about gold as promised in the title is played Jack Palance and Jack Palance is awesome.

Most hilarious quote:

Phil: Please don’t tell my kids I died taking a shit.

#280. Mannequin

Two Andrew McCarthy movies in the last eight?! It wouldn’t be a list of comedy movies without Andrew McCarthy. McCarthy practically owned the 1980s. You might think of Bill Murray or Michael J. Fox when you think of 1980s comedy flicks but neither of them are even in the same breath as McCarthy. And while we’re on the subject…two Meshach Taylor movies in the last three!? What a great romp. If Class Act was everything that was the early 1990s, then Mannequin was everything that was the late 1980s, by which I mean, seemingly horrific but with a memorable soundtrack featuring Starship.

Most hilarious quote:

Hollywood Montrose: You know I would never interrupt you when you’re getting a piece of wood…

#279. Big Momma’s House

Man, thank you Martin Lawrence. If not for you, unfunny fat black women would still be playing unfunny black women in movies instead of unfunny black men! If not for Martin Lawrence having one of his spells and convincing Hollywood that he is just crazy enough to play a fat women to hilarious results, the careers of Eddie Murphy,  the Wayans, and even Bugs Bunny would probably be over. And goodness, no one would even know who Tyler Perry is. Also, a key to the fat black man as a women genre is having a palpable character actor as the sidekick. This gives the ridiculous idea the very thin waft of credibility for the brief moment you consider seeing it. In this case, Paul Giamatti plays the part honorably.

Most hilarious quote:

Basketball Teen #1: Oh so granny think she got game?
Big Momma: Oh yes I got game. and I got two words for you: I’m back.
Basketball Teen #2: You too fat to be ballin’!
Big Momma: Say what? You look like a damn shaved bird!

#278. Citizen Kane

This is a classic comedy. First of all, you have what has to be the inspiration for all grumpy old men movies to come in the lead character, the iconic, Charles Kane. He’s Ebenezer Scrooge and your mean grandfather rolled into one melancholy old fart. Watching Kane’s life told by those that knew him best eventually leads to the crescendo when we discover that, ironically, it wasn’t money, wealth, and power that he always craved, but the wholesome joy of sledding on the freshest powder of his memories. It’s at that moment that you realize the joke has been on you along.

Most hilarious quote:

Charles Foster Kane: I run a couple of newspapers. What do you do?

#277. Ernest Scared Stupid

While Kane is considered by some to be the greatest American film of all time, comedy or not, let’s give some credit to Ernest Scared Stupid, as well. Not only does it have string bean funnyman Jim Varney playing his beloved character Ernest in one of his last big screen successes with the character, but the film also goes for big laughs with the likes of Eartha Kitt and Austin Nagler. Nagler, unfortunately would never be cast again for any movie, ever. While it might not be “hip”, or “couth,” to enjoy an Ernest film, sometimes it’s okay to laugh stupid.

Most hilarious quote:

Ernest P. Worrell: How ’bout a bumper sandwich, Boogerlips?