55 Best Comedies from the 2000s You Have to Watch (Again)

Best Comedies From The 2000s You Have To Watch (Again)

The 2000s were a magical time. It is a period trapped between the old and the new. It could be said it was even an innocent time in terms of what we were watching. This sense of freedom gave birth to some of the best comedies ever made. Comedies that dared to push the envelope, dared to be more adult, meta, and controversial than ever before.

This list will show you the best comedies from the 2000s that you need to watch (again).

Best Comedies from the 2000s

The list is mostly composed of American films, but we have made an effort to make it as diverse as possible. There are a lot of American comedies, but there are also some coming from the realm of animation, and even some from other countries. The point is that you can find old movies to rewatch and maybe some old ones you have forgotten about or never heard of.  

1. Shaun of the Dead (2004)

Best Comedies From The 2000s You Have To Watch (Again)

This is the film that put Edgar Wright on the map. From the outside, Shaun of the Dead might seem like a normal low-budget zombie film, but once you start watching, you will find that it is filled with clever jokes, excellent editing, and even a very powerful heartfelt core. This is clever humor snatched from the confines of a genre case.

2. Hot Fuzz (2007)

Best Comedies From The 2000s You Have To Watch (Again)

Hot Fuzz is another Edgar Wright flick. Coming from the success of Shaun of the Dead, Wright went in a different direction with Hot Fuzz, creating a buddy cop film with hilarious scenes and jokes that are still remembered to this day by the fan base. There’s also plenty of action, so you’re in for a treat.

The cast includes legendary actors such as Timothy Dalton, Bill Nighy, Simon Pegg, and Nick Frost, cementing their relationship as one of the best in the comedy stratosphere.

3. Superbad (2007)

Best Comedies From The 2000s You Have To Watch (Again)

A modern classic. Superbad is one of the funniest movies ever, taking the concept of a bunch of teens looking to party to the next level. It gave us tons of memes we keep using today, and it had one of the first important roles for Jonah Hill and Emma Stone, who would end up becoming superstars on all levels, winning tons of awards.

Also, this movie gave us McLovin, and there’s no way for you not to laugh watching his arc throughout the whole movie. It’s fantastic.


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4. Anchorman: The Legend of Ron Burgundy (2004)

Best Comedies From The 2000s You Have To Watch (Again)

Will Ferrell gave us some hilarious movies during the 2000s, but there is no better movie from him than the spectacular Anchorman. A satirical film directed by Adam McKay, who would later become an awards darling with films like The Big Short and Vice.

Anchorman manages to be funny every single second of its running time, and just for that, it should be seen again many times. You know, all those GIFs of Ferrell that you can use on social media? Well, this is the origin of all of those. It is good to remember how impactful this movie was on the internet, and there are many more great moments throughout the movie. 

5. Zombieland (2009)

Best Comedies From The 2000s You Have To Watch (Again)

Zombieland was another movie that took the zombie genre and twisted it into something funny instead of scary. But unlike Shaun of the Dead, which is the peak of British humor, Zombieland goes the way of the cowboy and gives us a great comedy set in America. Woody Harrelson is electric, and Emma Stone is just as good as ever.

The opening sequence is worth watching time and time again. Watch it enough times, and you and your friend will be making Blue Steel poses over and over again every time someone takes a picture of you. You have been warned. 

6. Tropic Thunder (2008)

Best Comedies From The 2000s You Have To Watch (Again)

Ben Stiller is another one of those directors that were on fire during this decade, delivering tons of great comedy movies, one after the other. Tropic Thunder has it all: it’s a war film with plenty of gore, and it stars Robert Downey Jr. in blackface and gets away with it.

It has Matthew McConaughey as the best agent an actor could want, and it also has Tom Cruise in a fat suit, being quite intimidating and saying tons of bad words.

This is a movie that got away with a lot of things, and that would be impossible to make in today’s climate. So go back and be impressed by everything that was allowed in movies less than two decades ago.

7. Burn After Reading (2008)

Best Comedies From The 2000s You Have To Watch (Again)

This is one of the weird ones, and it makes sense because this is the creation of the Cohen Brothers, a pair of directors that have always been unique in everything, including their humor. The plot of Burn After Reading is a mystery, no one knows what is happening. That is the point of the film, the absurd and crazy stuff that happens in life just because.

The movie has one of the best casts ever assembled. George Clooney, Frances McDormand, Brad Pitt, John Malkovich, Tilda Swinton, Richard Jenkins, and more give excellent, funny performances that will stay in your mind for a long time. 

8. The Hangover (2009)

Best Comedies From The 2000s You Have To Watch (Again)

There is a before and after to The Hangover. The crazy comedy put all its stars on the map, and it was one of the most successful comedies ever at the box office. Todd Philips, now better known for Joker, directs with grace and energy. Every single situation is hilarious, and the movie is in itself a great mystery.

There is also a live tiger wreaking havoc in a hotel, and Mike Tyson makes a cameo that doesn’t have the right to be as good as it is. You need to see it again just to remember how good it is.

9. Kiss Kiss Bang Bang (2005)

Best Comedies From The 2000s You Have To Watch (Again)

This one is a different class of comedy, Kiss Kiss Bang Bang is the brainchild of Shane Black, who uses sharp dialogue and a lot of black humor to create a powerful story of love, mystery, and tons of laughs.

The film also ignited the career of Robert Downey Jr. back on the road, and it allowed Val Kilmer to do a fantastic comedic role, of the kind that he had never done before. Without this movie, there wouldn’t be any MCU as we know it today. So, go back, watch it and pay your respects. 

10. The 40-Year-Old Virgin (2005)

Best Comedies From The 2000s You Have To Watch (Again)

Steve Carell is now an international superstar thanks to The Office and his many award-winning films, but once he was mostly unknown. The 40-Year-Old Virgin is an earnest and lovable film that talks about being comfortable with yourself and how that kind of confidence is the sexiest of them all.

There are, of course, tons of funny situations that come very organically thanks to the awesome premise. The movie is worth seeing just for the fact that there are tons of actors in it that were just waiting to explode in popularity. Going back and seeing it, it really makes clear that it was a stroke of luck to have them all together at once. 

11. Shrek (2001)

Best Comedies From The 2000s You Have To Watch (Again)

Shrek was a stroke of genius. The creators were able to create a story that is both a conscious fairy tale that is making fun of itself and a meta-commentary on storytelling as a whole. The animation might look somewhat dated by current standards, but the voice acting and the jokes still hold up.


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Mike Myers, Cameron Diaz, and Eddie Murphy do an incredible job of voicing the main characters. Their work on the movie actually opened the path for more top talent to go into voice acting. Sadly, the sequels were not as good as this one.

12. Knocked Up (2007)

Best Comedies From The 2000s You Have To Watch (Again)

This is the movie that put Seth Rogen on the map. And it still holds up as a very funny movie about growing up, being open-minded, and taking responsibility for your actions, but never forgetting to have fun and be yourself. For everybody growing up nowadays, it will be super relatable.

Cameos by James Franco, Jason Segel, Leslie Mann, and Paul Rudd make for an incredible cast of comedians all under one roof.

13. Forgetting Sarah Marshall (2008)

Best Comedies From The 2000s You Have To Watch (Again)

Talking about forgetting, Forgetting Sarah Marshall is indeed one of the best comedies around. It speaks to the universal truth of being heartbroken, and it does some really awesome stuff with it. The cast is excellent, letting Jason Seagel be the protagonist and casting Mila Kunis as the perfect romantic interest.

The movie even has a fantastic musical number executed by classic string puppets. Kristen Bell, Russell Brand, and Bill Hader play supporting roles that give the film that extra punch that others wish they could have. If you have ever felt heartbroken, this is the movie for you. 

14. School of Rock (2003)

Best Comedies From The 2000s You Have To Watch (Again)

One of the best Jack Black movies around. The film mixes the classic tale of a substitute teacher winning over his new students with heavy metal, and the results are hilarious. It helps a lot that Black himself is a metal music fan, as you can see his passion when he is teaching the kids all about the best bands and songs of the genre.

It also works as a great story of self-improvement if that is something you need to watch, and if you are a metal music fan, then this is a must-watch.

15. Elf (2003)

Best Comedies From The 2000s You Have To Watch (Again)

Every year, many TV networks, studios, and streaming platforms try to create the next Christmas movie classic, a film that can be seen for many, many years to come. It is a hard venture, but Elf did it, and it is still just as hilarious as ever. Will Farrell plays the role of a fake elf coming to the big city to meet his biological father.

The premise is absurd, but the jokes are as good as they can be. The rest of the cast is just as fantastic, and yeah, you can watch it every Christmas from now on. 

16. Wedding Crashers (2005)

Best Comedies From The 2000s You Have To Watch (Again)

Wedding Crashers is not the only Owen Wilson and Vince Vaughn pairing, but we think it is the best one. You can even see Bradley Cooper in a role way before he was so well known in Hollywood, and the legendary Christopher Walken manages to flex his comedic muscles quite a bit. His charm is just infectious.

The premise of a couple of wedding crashers going the extra mile on their mission is really funny and makes for a really light watch on any day of the week. 

17. Mean Girls (2004)

Best Comedies From The 2000s You Have To Watch (Again)

An instant modern classic. This movie skyrocketed the careers of many of its cast members, and it is one of those movies that has stood the test of time thanks to how quotable it is, so much that it has become the source of countless memes on the internet.


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They are all here: Tina Fey, and now Academy Award Nominee Amanda Seyfried. If you just want to remember why Regina is such an evil character, or maybe you have never seen it, this is a must rewatch. 

18. Zoolander (2001)

Best Comedies From The 2000s You Have To Watch (Again)

Zoolander tells the tale of a super fashion male model that loses his reputation and has to build it back in order to stop a shadow conspiracy in the world of fashion that threatens world peace. The premise of Zoolander is a crazy one, but it is even crazier because it works.

Ben Stiller and Owen Wilson kill it every step of the way, and the countless cameos are just fantastic. The sequel is best forgotten, but the original one is just fascinating and amazing as a comedy, showing the peak of every performer. 

19. Black Dynamite (2009)

Best Comedies From The 2000s You Have To Watch (Again)

In this hilarious parody of blaxploitation films from the 70s, Michael Jay White is Black Dynamite, the ultimate badass. Action star Michael Jay White becomes a comedian in this hilarious spoof of 1970s blaxploitation films. White is just incredible in the title role of a badass womanizer who always comes out on top, even in the most dangerous situations.

Just like the blaxploitation films of the 70s, Black Dynamite is a very adult film, so no kids in the room for this one. Even nowadays, nobody has made something like this with this level of success. 

20. Kung Fu Hustle (2004)

Best Comedies From The 2000s You Have To Watch (Again)

This is one of the most successful comedies in terms of box office ever released in cinemas. But very few people know about it here in the west. Kung Fu Hustle, just like Black Dynamite above, does a satirical take on the kung fu cinema genre and does so by using great visual effects, powerful performances, and tons of physical comedy.

The film works as a sort of live-action anime, with lots of action and a lot of heart. You will laugh and gasp with every new scene.

21. Shaolin Soccer (2001)

Best Comedies From The 2000s You Have To Watch (Again)

Before succeeding big with Kung Fu Hustle, Stephen Chow made his name around the world with Shaolin Soccer. This movie is one of the most hilarious sports movies you will ever see in your life. The film takes the sport to a new level thanks to some cool visual effects and the fact that the characters take every ridiculous situation at face value.


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Physical comedy isn’t as popular anymore in the west as it once was, but if you want to see what it is all about, this is the perfect movie for it.

22. Dodgeball (2005)

Best Comedies From The 2000s You Have To Watch (Again)

If Shaolin Soccer took soccer way too seriously, the same can be said for Dodgeball. Vince Vaughn is the protagonist in this movie, where a group of outcasts tries to save their gym from the hands of an evil businessman, and the only way to save it is to win a dodgeball tournament.

Hilarity ensues, and the matches are incredibly fun. It may not be as exciting as Shaolin Soccer, but it is the best sports bet on this side of the world.

23. Team America: World Police (2004)

Best Comedies From The 2000s You Have To Watch (Again)

Trey Parker and Matt Stone are living legends thanks to their work on South Park. So, when they decided to go in and make a movie, with puppets. It was expected that the result would be funny and very offensive. The fact that the movie stars puppets as the main characters is just the first layer of a movie that takes punches to basically everybody in the film industry and beyond.

The fact that some of the subjects tackled in the film are still relevant in today’s society only makes it more rewatchable. 

24. Super Troopers (2001)

Best Comedies From The 2000s You Have To Watch (Again)

Super Troopers is without a doubt the best cult classic on the list. For those who have been able to find this gem, it becomes a treasure to preserve. That’s why the movie has been living on the internet for more than twenty years.

It stars the comedy group Broken Lizard as a group of police troopers that are a bit more clueless than average. Good hearts and intentions make for some amazing comedy sequences and very quotable moments.

25. Napoleon Dynamite (2004)

Best Comedies From The 2000s You Have To Watch (Again)

For years after its release, Napoleon Dynamite was the king of the indie comedy scene. The strange character captivated the imagination of thousands of people, who identified with this eccentric outcast and his perspective on life.

Napoleon Dynamite might not be a movie with tons and tons of laughs, but the humor sentiment is earnest and genuine, and that’s more than many other films can attest to doing. 

26. Borat! Cultural Learnings of America for Make Benefit Glorious Nation of Kazakhstan (2006)

Best Comedies From The 2000s You Have To Watch (Again)

Yes, that is the complete title of the film, and just as you would expect from a title like that, the film is as absurd as it can be. The twist is that Borat presents an absurd world that is completely real, as it is the world we’re living in right now. The mockumentary made a worldwide star out of Sasha Baron Cohen, who has now become more of a serious actor.

Borat is a cultural icon at this point, and it is good to go back and see if things have changed a bit for the better since the movie came out.

27. Step Brothers

Best Comedies From The 2000s You Have To Watch (Again)

This is the last great movie out of the Ferrell and McKay collaboration. Step Brothers is a classic man-child film where Will Ferrell and the always underrated John C. Reilly take the roles of stepbrothers. For the sake of the older parents, they are big in age but small in mind.

The two get into hilarious situations as they learn to grow up and how to be brothers. So far, this might be the last great of Ferrell’s movies. Let’s hope the actor can make a comeback with many more movies in the future. We need them.

28. The Hitchhiker’s Guide to the Galaxy (2005)

Best Comedies From The 2000s You Have To Watch (Again)

This film is based on the classic comedy science fiction book of the same name by Douglas Adams. Adams was a master of the absurd, the surreal, and the funny, and the movie does its best effort to make the book justice. Martin Freeman, Zooey Deschanel, and Sam Rockwell make for a fantastic cast.

And as the cherry on top, the late Alan Rickman does the voice of an android with depression. You can’t invent this stuff, but oh never mind, you can. 

29. Jay and Silent Bob Strike Back (2001)

Best Comedies From The 2000s You Have To Watch (Again)

Jay and Silent Bob started as minor characters in the Kevin Smith universe of movies. So, when the news came that they were going to star in their own movie, expectations were high. This film screams new millennium all the way.

The jokes, references, and cameos are all the essence of the decade, so if you want to go back and experience what it was like to live in the year 2001, there is no better movie than this one.

30. Harold and Kumar Go to White Castle (2004)

Best Comedies From The 2000s You Have To Watch (Again)

The genre of stoner movies was very niche in the year 2004, and it still is today, but Harold and Kumar Go To White Castle made it mainstream, at least for a bit. What begins as two friends wanting to go to White Castle for some burgers, becomes an odyssey where anything can happen.

Neal Patrick Harris also made a comeback thanks to this movie and his hilarious cameo as a twisted, very twisted version of himself.

31. Bruce Almighty (2003)

Best Comedies From The 2000s You Have To Watch (Again)

Jim Carrey was once the master of comedy. No one could top his movies in terms of financial success and in how much of a crowd-pleaser they were. Bruce Almighty is Jim Carrey in his top form. The energy the actors expel is contagious and, yes, hilarious.

This movie even gave us Morgan Freeman as the perfect representation of God, that we didn’t know we needed. Jennifer Aniston also makes a great appearance to finish with a golden bow.

32. Idiocracy (2006)

Best Comedies From The 2000s You Have To Watch (Again)

Oh, boy! If we are talking about films from this decade that are still relevant now, the one at the top would be Idiocracy. Luke Wilson ends up traveling through time and the future USA is, well, very stupid.

It is crazy how some things this movie projected towards the future ended up happening for real but in a not-funny way. If you want to see a thorough visionary movie, then rewatch this. You will be surprised.

33. Bad Santa (2003)

Best Comedies From The 2000s You Have To Watch (Again)

Another modern classic for Christmas and what could be the biggest role in Billy Bob Thornton’s career. The tale of two thieves trying to commit a robbery on Christmas is the perfect fuel for some good old-fashioned black comedy. Bad Santa is cynical but also hopeful in some ways, which is very weird.

But overall, this strange mix of tones is what makes the movie uniquely funny. The movie was also the last live-action film by John Ritter before his death. The actor was one of the most powerful forces in American comedy during the 1980s. It is good to watch it and see such a legend spreading laughter all around.

34. Pirate Radio (2009)

Best Comedies From The 2000s You Have To Watch (Again)

This is another great example of the best of British humor. Pirate Radio tells the story of a pirate radio station that transmits from a boat and their fight to stay on the air against the establishment trying to shut them down. The cast is filled with amazing British comedians such as Bill Nighy, Rhys Ifans, and Nick Frost.

If not for the laughs, the film is well worth watching for its wonderful soundtrack, which is filled with absolute gems. So, no matter what, you will get something cool out of rewatching this hidden gem. 

35. Coffee and Cigarettes (2003)

Best Comedies From The 2000s You Have To Watch (Again)

Jim Jarmusch is known for being a cult director, making some of the most interesting films in the independent scene. One of those films is “Coffee and Cigarettes,” a collection of short films that are basically conversations between characters as they drink coffee and smoke cigarettes.

The humor is very dry, cynical, and adult, but some conversations are quite fascinating. If this is your kind of humor, don’t doubt giving it a watch.

36. My Sassy Girl (2001)

Best Comedies From The 2000s You Have To Watch (Again)

My Sassy Girl is one of the most successful comedies in South Korea. Based on a true story, the film tells the story of a young man meeting the love of his life, a sassy girl, whose name is never mentioned in the movie.

The comedy is as hilarious as it is very relatable, and for those who know gender roles in Asia, the film pushes against those conceptions quite hard. The film later spawned a whole franchise, with TV shows remaking the story in many different countries. 

37. Night at the Museum (2006)

Best Comedies From The 2000s You Have To Watch (Again)

Night at the Museum is directed by Shawn Levy, who would later become one of the minds behind Stranger Things and other great properties. Levy really knows how to make family-friendly films, and Night at the Museum is one of them. The story of a simple man trapped in a fantastic situation.

The movie is filled with many clever jokes and references to history that can make you even smarter if you go back later and research their origins. From all the movies on the list, this is the best one to watch on a family movie night and share laughter all together, as it should be.

38. Legally Blonde (2001)

Best Comedies From The 2000s You Have To Watch (Again)

Another modern classic. The film gave us the excellent Reese Witherspoon and gave us some of the most quotable lines ever. Legally Blonde became a feminist icon very quickly, showing us that feminist doesn’t mean rude or abusive. They can come in any shape or form and that is something that should be respected.

It also has Selma Blair, and what more could you want? The movie had a sequel a couple of years later, but so many years later, nothing can top the original. 

39. Bridget Jones’ Diary (2001)

Best Comedies From The 2000s You Have To Watch (Again)

Another feminist icon, but this time coming from England. Bridget Jones’ Diary upset the established conventions by making the protagonist an everyday woman. Renée Zellweger is, of course, a beautiful woman, but her depiction in the film goes against all the elegance that many other films and TV shows have made standard.

Colin Firth and Hugh Grant complete the cast. There were sequels, but the first one is still the best. 

40. The Proposal (2009)

Best Comedies From The 2000s You Have To Watch (Again)

The Proposal is the classic tale of opposites clashing and then falling in love. It is the classic template for romantic comedies. But not every comedy has Ryan Reynolds and Sandra Bullock as its protagonists. The two actors have amazing chemistry, and it is quite fun to watch them navigate their relationship.

The Proposal is nothing new at all, but the execution is what matters, and it makes up for the movie’s lack of originality. It’s comfort food in movie form at its best. 

41. Tenacious D in the Pick of Destiny (2006)

Best Comedies From The 2000s You Have To Watch (Again)

The Pick of Destiny is a musical, but not just any kind of musical. It is a metal music musical, and it also works as a sort of fictional origin story for Tenacious D, Jack Black, and Kyle Gass’ band in real life. The film has all sorts of references and cameos from all over the film and metal music world.

The songs are quite badass as well. Get on and take a journey through the metal world with these geniuses of the genre.

42. EuroTrip (2004)

Best Comedies From The 2000s You Have To Watch (Again)

If there is something that the 2000s gave us, it was a bunch of raunchy comedies. Some of them are pretty bad, and some of them are good. But out of the bunch, EuroTrip is the best. The movie is the definition of a road movie as a bunch of friends go to Europe, cross many borders, and get into a lot of problems.

Some situations are very crazy and might break your suspension of disbelief, but hey! All of it for the sake of making you laugh. 

43. Scary Movie (2000)

Best Comedies From The 2000s You Have To Watch (Again)

When Scary Movie was released in the year 2000, it felt like a revelation. All of a sudden, all the rules were broken, and this parody broke them all. By taking and mixing all the tropes the slasher film genre has used, culminating with the deconstruction of the genre with Scream, Scary Movie makes fun of everything, including the audience itself.

No one is safe in this movie, but the results are fantastic. Sadly, the success of the movie opened the door for many sequels that forgot what made this one such a breath of fresh air. 

44. Madagascar (2005)

Best Comedies From The 2000s You Have To Watch (Again)

Madagascar is one of those underrated animated films. There were many of them throughout the 2000s, but Madagascar knew they couldn’t just sustain themselves by using pop culture references without creating characters worth investing in. Madagascar creates such characters; in fact, it creates a slew of them, and the films hold up exceptionally well even today.

The film spawned two more sequels, all of them of great quality. So, if you love animals and comedy, this is the franchise for you.

45. 13 Going 30 (2004)

Best Comedies From The 2000s You Have To Watch (Again)

Another romantic comedy that really knows how to appeal to a universal feeling to make the audience invested in the story. 13 Going 30 has Jennifer Garner and Mark Ruffalo having some amazing chemistry and being the perfect couple. You just want them to get together.

The supporting cast in this movie is hilarious and makes for some really memorable scenes. It will be very easy for you to have a smile on your face from beginning to end. The film also includes the fantastic Andy Serkis in one of his few roles where you can actually see his face without prosthetics or CGI to hide it. 

46. The Girl Next Door (2004)

Best Comedies From The 2000s You Have To Watch (Again)

The Girl Next Door makes the fantasy of every man a reality. What would happen if you could date your favorite adult movie star? The answer is more complicated than you think, and it makes for some hilarious sequences, but it also gives a lot of room for reflection.

Adult movie actors are often stigmatized for their career choices, and people often forget that they are humans with dreams and feelings just like anyone else. Watching the movie will make you laugh, but also rethink how you see the people working in this industry.

47. Bubba Ho-Tep (2002)

Best Comedies From The 2000s You Have To Watch (Again)

Bubba Ho-Tep is a weird film, not only because its premise is basically that Elvis Presley, who hasn’t died, and John F. Kennedy, who hasn’t died either and is now black; are trapped in a nursing home fighting an ancient Egyptian mummy.

But also because the absolutely crazy premise works in such an excellent way that you cannot stop the need to stop yourself and ask, “What am I watching?” It doesn’t matter what you think you are watching while experiencing this movie; it’s just funny, and you should just go with the flow.

48. Kung Fu Panda (2008)

Best Comedies From The 2000s You Have To Watch (Again)

Another Jack Black movie? Yes, of course. The man can not stop being funny, not even in animated form. Kung Fu Panda, like the previously mentioned Kung Fu Hustle, takes the tropes from the kung fu film genre and mixes them with western sensibilities, a heartwarming story, and tons of jokes.

There are also some really cool action sequences that take advantage of everything the animation medium has to offer. Go back and give it a watch. It has really pure good vibes and awesomeness. 

49. Funny People (2009)

Best Comedies From The 2000s You Have To Watch (Again)

Funny People is, well, about funny people. A movie about comedians and what makes them tick. Seth Rogen and Adam Sandler make a good couple, as they try to navigate the world of stand-up comedy.

It is a long movie, and it might be the most serious movie on the list, but it doesn’t matter; there are still a lot of laughs to be had here. Go into it with an open mind, and you will discover that there are many sides to comedy. 

50. I Love You, Man (2009)

Best Comedies From The 2000s You Have To Watch (Again)

I Love You, Man is what we could call a perfect title, as it tells you exactly what the movie is about. Most romantic comedies have to do with a girl meeting a boy or vice versa, but not many movies have to do with a man meeting another man, and not in a romantic way, but as friends.

The friendship between men is often represented as rough, but the friendship represented in this movie is pure and funny as hell. The movie has Paul Rudd and Jason Segel in the main roles, and the casting couldn’t be more perfect, as both bring their high levels of charisma to the picture and make it insanely better.

51. What Women Want (2000)

Best Comedies From The 2000s You Have To Watch (Again)

This is one of the oldest titles on the list, but it is also one of the best. Men and women are always depicted as different, and yes, they are different in many ways, but at the core, we all expect most of the same things from life; love, respect, and well-being.

What the characters in the movie go through to find this out is hilarious, and we wouldn’t want it any other way. Mel Gibson and Helen Hunt are in the starring roles, and they are as good as ever, real movie stars.

52. Meet The Parents (2000)

Best Comedies From The 2000s You Have To Watch (Again)

Ben Stiller made this classic along with one of the biggest and most legendary actors in all of Hollywood; Robert De Niro. De Niro goes full into the role of a nightmare father-in-law that will make Stiller’s life hell, as he thinks Stiller isn’t the best man for his daughter.

The movie moves between grounded and absurd very elegantly, and the antics the characters go through are some of the best put on screen. The interrogation scene alone is well worth a rewatch.

53. A Serious Man (2009)

Best Comedies From The 2000s You Have To Watch (Again)

Like their previous movie on the list, the Coen Brothers don’t really follow any sort of conventions when they are making a movie, and this, another one of their comedies, follows that exact trend. The life of a normal man and the temptations that try to take him away from his seemingly perfect life.

The movie is a sort of parable, and the humor is potent, direct, and very dark at times. It might not be for everyone, but for those that want to go beyond the shallowness of the genre, A Serious Man will give a lot of food for thought to anyone who is interested.

54. Cloudy with a Chance of Meatballs (2009)

Best Comedies From The 2000s You Have To Watch (Again)

Another animated movie, this time coming from two of the best comedic minds in the business, Phil Lord and Christopher Miller. They were on fire during this time in their careers, and this movie gave them enough cloud that they ended up directing 21 Jump Street and even producing the Into The Spider-Verse movies.

Cloudy with a Chance of Meatballs is full of imagination, a beautiful art style, and a powerful message about self-discovery and how important the environment is to all of us who live on this planet.

55. In Bruges (2008)

Best Comedies From The 2000s You Have To Watch (Again)

In Bruges is a very unconventional comedy. Coming from the mind of Martin McDonagh, the script won Best Original Screenplay at the Oscars, which should tell you just how good it is. It tells the tale of two hitmen hiding in Bruges, Belgium. The film goes into some very dark places, but it never forgets it is a comedy and even treats these darker moments with a lot of grace and joy.

Colin Farrell and Brendan Gleeson make for an amazing pair, and the always good Ralph Fiennes kills it as the funny and intimidating character of Harry Waters. Go back, watch it, and be impressed by its cleverness.