Top 25 Comedy Films

25. I Heart Huckabees
While many people I’ve talked to have found this film to be either bizarre or just terrible, I found it to be both hilarious and charming. I’m sure there’s some message in the film that they were trying to get across to us all, but to be honest I didn’t catch it. I was enjoying the unique characters and interesting situations more than anything. Mark Wahlberg is actually bearable in this film and I found his character to be the most humorous.
Of course at times there seems to be scenes/ideas that push too hard and seem to be hitting you in the face with some kind of moral to the story, but I didn’t find it present enough to deter my enjoyment from the film. A pretty stellar cast too, with Jason Schwartzman, Dustin Hoffman, Lily Tomlin, Naomi Watts, Jude Law, and Wahlberg headlining.
Best Moment: During a dinner scene with devout Christians, Mark Wahlberg’s character berates them for using petroleum and ruining the world. The father angrily screams that ‘God gave us oil! He gave it to us! How can a gift from God be bad?’

24. Office Space
Mike Judge is the mastermind behind this picture, who’s most well-known as the creator/voice of Beavis & Butthead. This movie did terrible at the box office and was deemed a failure at first, but once it hit DVD it developed a cult following, as so many box-office failures often do. The movie seemed to capture office work pretty well, or so I’m told (I’ve never worked in an office) but the reason I loved it so much was due to the very subtle humor, something I wasn’t used to growing up with Jim Carrey.
While most people associate the film automatically with Stephen Root’s stapler-hoarding character Milton, I find the majority of the secondary characters much more entertaining to watch, like Michael Bolton and Tom(Richard Riehle, who is awesome) with his ‘Jump-to-Conclusions Mat.’
Best Moment: The conversation involving Michael Bolton’s name and why he won’t change it, as well as any subsequent referral to his name and the famed singer.

23. There’s Something About Mary
Most everyone knows about this movie, and it’s what really put Ben Stiller in the spotlight and opened up his career (which could be a good or bad thing depending how you look at it). It is a great ensemble piece about this one girl who drives everyone crazy, and attracts so many different wierdos and creeps. Which is why we’re thankful that in the end, the nice guy who means well gets the girl, even if he has to go through many hilarious hijinks along the way.
Best Moment: When Ted picks up a strange hitchhiker (played by Harland Williams) he begins to rant about his idea for a 7-minute workout and other strange things.

22. Team America: World Police
Trey Parker and Matt Stone created South Park, and were almost immediately rich and famous. They also attempted a major motion picture, ‘Baseketball,’ which was not a huge success (and not that funny in my opinion). They unleashed this movie five years later, and did much better with critics and fans alike. It was shot using marionnettes(or if you prefer, puppets), something I don’t recall seeing since the classic TV Show ‘Thunderbirds!’ I think the choice to use puppets enhanced the humor quite a bit, as the movements and facial expressions were limited and yet still gave better performances than Keanu Reeves ever could (hey oh!).
There are many shots taken on actors and the Screen Actors Guild (or for this movie, ‘Film Actors Guild’ a.k.a. F.A.G.) and it’s great to hear people like George Clooney and Matt Damon took the film so good-naturedly. In fact they had said that if Trey and Matt hadn’t included them in the film they would have been insulted.
Best Moment: When Gary is undercover with the Terrorists, he is being chased down by Team America and tries to give them ‘the signal’ which involves flailing his arms wildly. They don’t clue in that it’s him and continue their pursuit.

21. South Park: Bigger, Longer, & Uncut
I’ll admit that when South Park first came on the air, I hated it. I thought it was crude, stupid, and terribly unfunny. The fact that many of my friends instantly loved it and quoted it all the time didn’t help things. But as the show progressed, I began to see how funny and intelligent the show’s creators were. I still think the first few seasons are pretty bad, but season 4 onward are gold, Jerry, gold!
The movie was definitely a great addition to the South Park universe as well. Not only that, but it’s a musical, which makes me love it by default. The songs are great, and the plotline is pretty epic and flows well. There are plenty of movie/tv references littered throughout which for some reason I always felt only I fully understood.
Best Moment: While all the music in the film is brilliant, the one that stands out to me is ‘What Would Brian Boitano Do?’ which is random and hilarious, but also very catchy!

20. Old School
This film is interesting because Will Ferrel, one of the three main stars, was still mostly known for his work on Saturday Night Live. I think this film is what really helped him break into the film ‘industry’ and made him more recognizable to those who never saw him on SNL.
While I’m not the biggest Luke Wilson fan, he does just fine in this film as the everyman, and it’s really Vince Vaughn and Will Ferrel who shine with their characters. Also the show gets bonus points for featuring a pre-LOST John Locke.
Best Moment: While I definitely have to give the edge to Will Ferrel’s streaking scene, I actually think the bit just preceding that is the best, where he interrupts Snoop Dogg’s performance and tells his friend to ‘bring his green hat.’

19. School of Rock
Jack Black is something of a hero of mine. Looking at him he doesn’t seem to be a ‘leading-man’ and yet he’s been able to become one of the greatest comedic actors/musicians due to dedication and lots of talent. He’s been in a bunch of films before this one came around, and usually as a co-star and rarely as the lead. This is definitely his best ’starring role’ and I absolutely love it. Not only that but the kids in the movie are all real musicians and play all their own instruments which is pretty impressive.
Best Moment: The final performance at the climax of the film with the school’s band, which is pretty damn awesome.

18. Super Troopers
After this movie came out I was sure the Broken Lizard team (writers/director/stars of this film) would be the next big thing. Unfortunately I was wrong, as their two follow ups to this excellent comedy were Club Dread and Beerfest, which I felt were very unfunny and sincerely lacking in the laughs department. But no matter, that doesn’t stop this film from being a hilarious take on highway patrolmen, who seem to enjoy playing games on the people they pull over more than enforcing the law. The overall story arc is kind of boring, but the random jokes interweaved throughout the main plot are enough to save it from being a snoozer.
Best Moment: When they play a game where the officer says ‘meow’ every so often while talking to one of their many ‘victims’ and acts offended when said victim calls him on it.

17. Wedding Crashers
Another ‘Frat Pack’ comedy, this movie was one of the few recent comedies that I could not stop laughing at while watching in the theater. I think Vince Vaughn is a great comedic actor and he really sells this movie for me. Owen Wilson is another guy I enjoy, and although sometimes I feel he’s playing the exact same character he always does, I thought he played it well in this film.
There are some great performances by the other cast members as well. Christopher Walken is someone I can never dislike in a movie, even if I dislike the movie itself. Will Ferrel makes a great cameo and the two leading ladies are pretty great as well (Isla Fischer and Rachel McAdams). It’s hard not to enjoy watching this movie.
Best Moment: Vince Vaughn has a lot of great rants in this movie, but one of the best ones was when he talks about “Motorboatin’.”

16. Airplane!
One of the more ‘classic’ movies on this list, and it’s one of the best. It was one of the first parody or ’spoof’ movies (about disaster films mostly) and it was executed really well. Leslie Nielsen stars in one of his most subtle performances and probably my favorite. There are a lot of memorable lines and he delivers a lot of them. There’s a pretty big array of characters and they are all funny. Of course I’m not even sure what has happened to most of the actors from this film aside from Nielsen. I know they made a sequel to this movie but from what I’ve seen it’s not nearly as funny as this timeless classic.
Best Moment: “Surely you can’t be serious?” “I am serious. And don’t call me Shirley.”

15. Anchorman: The Legend of Ron Burgundy
In retrospect, this movie is not nearly as great as I remembered it the first time I watched it. Still, it’s one of the better Will Ferrel comedies, most likely due to the strong supporting cast and Steve Carrell as the overly-quoted Brick Tamland. The humor relies heavily on absurdity, and for the most part it pays off. There is also a large amount of cameos by other comedians/actors, and it was pretty fun to spot them all for the first time.
One of the many films that uses a heavy dose of improvisation for the funniest bits. They had a lot of takes for many of the scenes, with the actors improvising their lines, which often becomes much more funny than anything scripted.
Best Moment: The big news-person brawl in the street was a little over the top, but the conversation that takes place immediately afterwards about how out of hand things got was priceless.

14. Tommy Boy
Chris Farley is, unfortunately, one of the many celebrities who passed away long before they should have. This film is what I always associate with Chris Farley, and I think it stands as some of his best work. He just acts so loveable, and dimwitted yet charming. I am not a huge David Spade fan and I like him a lot better when he’s playing the straight man to Farley’s zanyness.
It’s also a fairly decent story, albeit nothing I’ve never seen before. But the fact that someone like Tommy could get the girl, save the company, and achieve the respect of his coworkers, is a pretty great thing.
Best Moment: Tommy is trying to sell brake pads, and he decides the best way to do so is to give the potential buyer a demonstration of what would happen without the brake pads. The presentation is downright brilliant, complete with screaming, fire, and a paddywagon.

13. Hot Fuzz
I will warn you right now that if I ever do a Top 25 Action Movies this film will definitely be on there as well.
One of the best movies I’ve seen in a long time, Hot Fuzz is the next movie by the creators and stars of Shaun of the Dead. This time it’s a sendup of action/buddy cop movies, and it is brilliantly executed. They manage to parody as well as tribute action movies, and the final scene of action is probably the greatest action sequence ever put to film.
But that doesn’t mean the comedy takes a backseat to the action. The british wit is ever present here, and the editing and bits of improvisation are executed flawlessly. You’ll be laughing but also amazed at how intense the action is, and not many films can do that. But on top of that, the main plot of the film is a very original one and something I did not see coming. There’s just not enough good things that I can say about this movie.
Best Moment: From the moment Nicholas Angel drives up to town and kicks on old lady in the face until the final climactic moment, the main climax of this film is worth your time alone.

12. Zoolander
This is probably one of the first ’so stupid it’s funny’ movies starring people like Ben Stiller and Will Ferrel. And it is. Incredibly stupid. But it’s also incredibly entertaining. The movie holds a special place in my heart because it is one of the first movies I went to with real, genuine friends, and we spent another hour or so outside of the movie theater remembering the hilarious movie we just witnessed. It was a really fun evening and I will always remember this movie because of it.
There are also some notable cameos, including, most awesomely, David Bowie as the Walk-Off judge. It’s hard to describe this movie without making it sound terrible, but it’s about Male Modeling and it lampoons the business as well as the participants. But it also does it in a very loving way, so I’m sure the real male models of the world don’t mind.
Best Moment: Derek Zoolander and his male modeling roommates/friends are at the gas station and goofing around, when eventually things escalate to the point of them having a full out gasoline fight, spraying gasoline and dancing around to the tune of ‘Wake me up Before You Go-Go.’

11. The Big Lebowski
The Coen brothers are geniuses, and this is one of their best films. John Goodman is brilliant as the crazy War Veteran and Jeff Bridges definitely is ‘The Dude.’ Really though there are so many great actors in this movie and I can’t name them all, but everyone involved is exceptional. I especially love Steve Buscemi, even though he doesn’t get many lines at all (an in joke due to his excessive amount of talking in their previous film, Fargo).
The story line is pretty convoluted and interweaving and it goes all over the place with twists and turns, and throughout it all The Dude just wanted his carpet replaced. It really held the room together.
Best Moment: When John Goodman thinks a nice car belongs to a kid who has information they need, he starts destroying it with a crowbar, yelling at the kid ‘This is what happens when you fuck a stranger in the ass!’

10. Dumb and Dumber
I remember when Jim Carrey first came on the scene with Ace Ventura – I thought he was brilliant and I loved that movie more than anything. Granted I was pretty young, but even today it stands as a great comedy (and almost made this list). But I thought he really got to shine in this movie which implies right from the title that it’s going to be stupid. It is pretty stupid, but it is also littered with some pretty clever comedy. Jeff Daniels is alright in this film as well, but he works better as a friend for Jim Carrey to work off of, as I’m pretty sure his character is the latter of the two from the title.
Best Moment: When Seabass enters the bathroom stall Lloyd is inhabiting, Jim Carrey has the most perfect scream/facial expression ever put to film.

9. Tenacious D in The Pick of Destiny
Okay, I confess I am a sucker for musicals. Pretty much any film that I hated could be put entirely to song and I’d probably like it. Except Swimfan. That movie blew all kinds of chunks. Tenacious D have always been awesome, and I loved their HBO show and their first album, so I was pretty sure I’d love this movie. I heard the soundtrack long before seeing the movie and was kind of…disappointed. I don’t know why, they just seemed like terrible songs at the time. It was only after seeing the movie that I was able to appreciate it fully, and I think you really do need to see the songs in context with the story of the film to understand and appreciate them the way they should be.
That being said, my GOD what an awesome movie this was. I was surprised and confused as to why it didn’t make more money in the box office, but I guess people would rather see Adam Sandler pretend to be gay than a genuinely funny movie about rock and occasionally about roll. Jack Black is in the part he was born to play, himself, and the many cameos by friends and allusions to their HBO show are played perfectly.
Best Moment: During the Gig Simulation, JB attempts a power slide and falls on his guitar, which causes him to cry out in pain and exhasperation. After proclaiming sadly that ‘I broke Monster Mash(his guitar)!’ he mumbles incoherently about his performance and it’s just delivered perfectly.

8. Ghostbusters
A classic! How can anyone not like Ghostbusters? Every kid wanted to be a ghostbuster after this movie came out. It’s a really great story, and so many great comedians grace the screen during the course of the film. Bill Murray obviously is the stand out, and it was in this movie he really perfected being Bill Murray. I was also impressed by Rick Moranis, he played the dimwitted nerdy guy to a degree where he was loveable yet you still wanted to shout NEEEEERRRDDDDDD at him.
Fun fact: Bill Murray plays Venkman in the film, and Lorenzo Music voices the character in the cartoon series based on the film. Music is also the voice of Garfield in the animated show, and none other than Bill Murray voiced Garfield in the live action version! (Garfield sucked though)
Best Moment: Louis is hosting a party with his fellow nerds, and after announcing to the room ‘Hey does anyone wanna play Parcheesi?’ the hell hound bursts through the door and he unfazedly asks ‘Okay, who brought the dog?’

7. Snatch
There are many who may not think of this show as a comedy, but if you aren’t laughing at the dry british wit laced throughout this brilliant heist/ensemble film, then there is something wrong with you. Guy Ritchie was a great director before he married Madonna, and this is my favorite of his movies. Lock Stock & Two Smoking Barrels almost made this list, but it was edged out just barely (I believe it was indeed #26). Either way, this was an amazing film and one that I can watch constantly over and over again without becoming bored.
Aside from the comedy and the great dialogue, there are a few scenes which have perfect uses of a soundtrack I’ve ever seen. When the dog is chasing the rabbit intercut with the mobsters chasing down/catching the big guy(his name escapes me), and when Mickey finds his trailer on fire are made so much better by the choice of music.
Best Moment: The aforementioned moment when Mickey discovers his trailer on fire, accompanied by the song ‘Angel’ by Massive Attack.

6. Fargo
This movie is full of comedy, but the thing that I loved the most was the completely unique characters from all the main actors. William H. Macy, Steve Buscemi, Frances McDormand and Peter Stormare are all amazing, and so different from each other. The accent used throughout by Macy and McDormand and others is hilarious, and delivered so perfectly.
Of course the movie uses an excessive amount of violence, but while it can be pretty gruesome a lot of the violence just ends up being funny as well, due to the way it is presented. Almost anyone who has seen this movie always relates it – appropriately so – to the woodchipper scene.
Best Moment: The bumbling of Macy’s character, Jerry Lundegaard, is painfully funny to watch. He’s such a bad liar but he gets so upset when people don’t listen to him, and he doesn’t seem like a smart enough person to pull off what he does (although not for long).

5. Shaun of the Dead
Honestly, I think this is one of the best movies ever made by mankind. It’s bloody brilliant, and the leading stars (Simon Pegg and Nick Frost) are so good at what they do. The movie is described as a ‘Rom-Com-Zom’ or a Romantic Comedy with Zombies, and it definitely delivers on what it promises. Zombie movies have always been awesome, but this one makes it even more enjoyable to watch because it’s so funny as well.
It requires repeat viewings, because one thing you’ll notice while watching it a second time is that there are so many little things littered throughout that allude to future/past events in the movie. Nothing is wasted and seemingly trivial things early in the movie end up being important when the gang is faced by the living impaired.
Best Moment: Their is a single zombie attacking the gang inside the pub, and when bumped the jukebox starts playing Queen’s “Don’t stop me Now” and they continue to pummel the zombie with weapons, completely on the beat of the song.

4. The 40 Year Old Virgin
This is such a sweet story, and hilariously told. Andy is such a nice guy, and they really make you feel for him and Steve Carrell plays him so honestly that it’s just a brilliant performance. While they could easily have made him a huge annoying nerd that everyone hates, they decided to make him a loveable nerd. Someone who just loves what he wants, and doesn’t let anyone tell him it’s wrong. I admire that. Of course this was made by Judd Apatow, who was a large part of the team behind Freaks & Geeks and Undeclared. That alone should tell you how high quality this film really is.
But throughout all that there are so many hilarious moments, like Anchorman before it largely due to improvisation by the talented actors. There’s no Will Ferrel or Ben Stiller cameos, which had started to become a bit of a cliché for comedy films, and it definitely didn’t hurt it, as the actors present here are insanely talented and capable of bringing the funny without a hand from the ‘heavyweights’ as it were.
Best Moment: When Andy is confronted by his friend’s girlfriend, who found a card describing various women from a speed dating service, Andy has to pretend it was his card and talks ‘jive’ to her to pass it off.

3. The Jerk
Another classic film, and probably the one where I actually enjoy Steve Martin a lot. I think he is perfect for this type of character, the loveable dimwit (there seem to be a lot of those on this list, I’ve noticed), and there are many genuinely funny moments that I just can’t help but love.
The story is pretty weird, and basically tells the story of Navin Johnson who leaves his black foster family once he discovers rythym, and goes on many adventures in his quest to find himself. He wins a lot of money from an invention he helped develop, and loses it all just as fast. It’s pretty interesting stuff, and it serves as a perfect plot for many great jokes.
Best Moment: An insane sniper picks Navin’s name at random from the telephone book, and tries to take him out at his job, instead shooting the paint cans right by him. Navin sees him and proclaims “He hates these cans! Stay away from the cans!”

2. Monty Python & The Holy Grail
Of course this is on here. I don’t care how many nerds can quote the entire thing, this is still a great comedy and one of the best ever made. Monty Python are brilliant and smart, and they are all on the top of their game in this movie directed by Terry Gilliam. The quest for the Holy Grail has never been so inherently funny, and the humor from Flying Circus is still ever present here.
There were a few movies that have become ‘tainted’ for me due to audience reaction to them, most notably Borat and Napoleon Dynamite. I still like the movies and I laughed my ass off the first time I saw them. But the fact that everyone seems to have a Borat/Napoleon impression that they just HAVE to share with me all the time, it makes watching the actual movie less enjoyable. That being said, this is one of the few movies that can withstand over-quoting from the fanbase, and no matter how many people say ‘Ni’ to me I still find it hilarious when watching the movie. If that’s not saying something for the quality of the film, I don’t know what is.
Best Moment: There really are too many to name. But I think my favorite is still the sequence with the witch on trial, and the ‘logical’ steps taken to get to the conclusion that yes, they should burn her.

1. A Fish Called Wanda
I guess if you’ve seen this movie, hopefully you understand why I picked it as my number one Comedy movie. It really is amazingly funny, with both John Cleese and Michael Palin of Monty Python doing some excellent performances. Of course Kevin Kline is hilarious in this as well, and it’s his interaction with Ted(Palin) that makes me laugh the most. John Cleese and his genuine love for Wanda is great, and the lies and excuses he makes to his wife throughout is just great.
Many people have not seen this movie, and I myself was guilty of that as well until a few years ago. It’s definitely a classic that everyone should see at one point. The interactions between the four main characters is really what sells this film, and I really love watching it over and over again.
Best Moment: Ted has a stutter. When Cleese’s character finds him tied up and with fries up his nose, he tries to get information out of him as to Otto’s location, but due to his stutter he has a hard time, so Cleese eggs him on, his frustration clearly visible. “Sing it!”