The Top 20 Comedy Movies of the 21st Century

The film industry has kept us entertained with some of the most hilarious comedies to hit the screen in the 21st century. We’ve watched the evolution of the business change with us as the younger generation has emerged with their own notions of what is considered to be funny. Practically anything that takes the less than inviting parts of real life situations and shows the parts we can all laugh at is appreciated. New players have stepped up to the plate and are filling the shoes of their comedian predecessors with just what the country needs right now.

Hey, life can become intense and uncomfortable at times so what we all need is a good movie to help us see the humor in it all. A good laugh can keep us sane and help us to lighten up just when it’s needed. For this, we’ve chosen the top 20 comedy movies (in no particular order) of the 21st century. If you’re feeling tense, browse through the selection and prepare to be entertained.

Superbad (2007)

Superbad takes adults back to senior year in high school. Who hasn’t been on the hunt for booze and the chance to have sex? This film is what happens when you have Evan Goldberg and Seth Rogan at the helm. Jonah Hill and Michael Cera team up under the direction of Greg Mottola to deliver performances that make us laugh and remember what it was like back then. We get to see male friendship at its finest. Throw in a couple of cops who are fun loving and looking for some nostalgic entertainment themselves and you’ve got a winning cast of characters that do not fail to deliver the ups, the downs and the laughs.

Borat:Cultural Learnings of America For Make Benefit Glorious Nation of Kazakhstan (2006)

The best way to laugh off being offended at the cultural level is to watch this film. Sacha Baron Cohen is the master and it gives everyone permission to loosen up and laugh at the rampant racism in our country. The fact that most Americans who helped in the filming of this film were unaware, makes it all the better. Yeah, Sacha is a racist, but he helps everyone to take a good long look at the ridiculousness of being that way along with a good dose of laughter while we’re getting the message. This comedy brings everyone together and the outlandish, racist, rude, culturally insensitive moves that we see from Borat are actually refreshing. Here’s your dose of reality and humor for the day.

Step Brothers (2008)

This is what happens when your 40 year old son acts like he’s 12 or 13. John C. Reilly and Will Ferrell are the ideal match for immature sons who are each living with a parent when their folks meet, fall in love and marry. Inane comedy that is so off the wall it’s hilarious. As with any blended family, the boys need to adjust to their new step parents and one another, but once they work through their differences, they become the best of friends. They go through what you would expect from young teen boys, except these dudes are funny. Lets see how inane two grown men can be. They’re enough to wreck a marriage, but also family minded enough to bring their folks back together. If you want to be truly entertained, then you’ll come to the “fucking Catalina Wine Mixer” and have some fun.

40 year old virgin (2005)

Steve Carrell is unforgettable as a forty year old man who has never been with a woman. The guys he’s trying to build a friendship with suspect he doesn’t have the experience that he claims and they bait him into describing the feel of a woman’s breast. His description doesn’t even come close. Sandbags…really? After the initial shock and laughter, they feel sorry for him and attempt to help him make his first score. Hilariously funny, but equally moving, we see two stories unfolding. Andy (Carrell) is taken into the group by Seth Rogen, Romany Malco and Paul Rudd, and he manages to find the romantic love for which he’s been waiting so long. The supporting cast boost this ribald comedy to the ceiling of entertainment and the story line is somewhat touching as well.

Zoolander (2001)

Ben Stiller is not only the star of the film, but also the director. He nails the character to a T showing charm, endearing qualities and also stupidity beyond reason. His sense of style leaves us cringing but he pulls it off with comedic relief being his salvation. This is the tale of models who have been brainwashed to become assassins for a group of neer do well manufacturers of clothing. The Villain seems to be smart enough to understand how absurd his world is and this is a bit frustrating for him. He delivers some intensity to the hilarious story line and there is a blend of sleuthing, drama and over the top humor infused into the scenes as only Ben Stiller can deliver.

Wedding Crashers (2005)

Owen Wilson and Vince Vaughn are John Becckwith and Jeremy Grey. The pair are dedicated womanizers who take advantage of local weddings to put the moves on the chicks in attendance. They have a falling out when John falls in love and the fight is on in this funny film about male friendship and romance.

Team America: World Police (2004)

Gary Johnston is a famous actor on broadway. Team America, the elite group of counter-terrorists, recruit him to join their team. The film is packed with action, romance and humor as Johnston and Team America fight terrorists and he goes solo in trying to avoid falling in love.

Old School (2003)

Todd Phillips directs Luke Wilson, Will Ferrell and Vince Vaugh in this coedy about 3 buddies that want to get back to the good old days. The trio open a fraternity near their old college and start recruitment. The zany adventures that they encounter trying to keep the frat going while battling jealous opposing frats and college administration is hilarious.

Forgetting Sarah Marshall (2008)

Kristen Bell, Paul Rudd and Jason Segal head the cast of this romantic comedy drama directed by Nicholas Stoller. Peter is dating his television star girlfriend Sarah Marshall. Their breakup devastates him so he decides to go on vacation to Hawaii to heal. He has no idea that is ex is booked at the same resort with her new squeeze. There are some sticky moments, some cute and romantic ones and tons of laughs because of the awkward and hilarious events that transpire.

Napoleon Dynamite (2004)

Jon Heder, Efren Ramirez and Jon Gries lead tha pack in this film about a laid back teen that is alienated from the rest of the world takes up the cause of helping his new buddy run for class president. Jon Heder does a great job of acting like a listless teen that doesn’t get easily excited. We’re all relieved when he comes up with a few brilliant plans because it shows that there is actually a light on upstairs. He lives with an odd family so it’s not difficult to understand why he comes off as being weird. Half of the hilarity of this film is because the characters are so damned odd.

21 Jump Street (2012)

Phil Lord and Christopher Miller direct super funny stars Jonah Hill, Channing Tatum, Ice Cube and Brie Larson in this funny film about what happens when adults go back to high school. Two of the most underachieving cops on the force are assigned undercover work. They go back to high school as students and attempt to blend in with the kids. Their goal is to infiltrate and bring down a drug ring that is dealing in synthetics.

Shaun of the Dead (2004)

Who says British films aren’t the kind of humor Amercans love? This Edgar Wright film is not only entertaining, its funny on a few levels. We get the best of horror and comedy rolled into one. Simon Pegg gives the performance of his life. He battles the undead zombies when the apocalypse hits, and brings a group of followers with him. The duality of the character is amazing. We get to see him accidentally make a few right choices as the bungler who stumbles into some luck that saves their lives. Pegg is hilarious and there are times in the film when we’re not sure if he’s smart or not.

Pineapple Express (2008)

Seth Rogen, Gary Cole, James Franco and Danny McBride are truly funny. A process server (Rogen) and his pot dealer (Franco) become the best of friends as they work together to stay alive. Rogen witnesses a murder and the perp is tied in with the police department. This makes it doubly tough as the pair attempt to bring the bad guys down while avoiding their thugs.

Knocked Up (2007)

How many movies move the critics to label them “an instant classic?” This one for certain. Seth Rogan and Katheryn Heigl lead the cast of this incredibly funny take on one night stand induced pregnancy. The jokes fly high but Judd Apatow’s comedy is tempered with some serious moments that give the film a perfect balance. It draws you in because the story gives a rendition of how real people would behave in this situation. Ups, downs, drama, laughter, tender moments and brilliant acting make this one a must see if you haven’t already. If it’s been a while, it may be time to watch it again.

Deadpool (2016)

This recently released film has made big waves in the comedy film genre. Ryan Reynolds adds the ultimate in humor to this comedic take on the character Deadpool. Reynolds is a merc that has a quirky sense of humor. When an experiment gives him amazing rejuenative healing powers, he seems unstoppable, but he is so disfigured that he wears the mask and costume to cover the scars. He’s out for revenge but seems to find a way to make even the most gruesome and painful scenes funny.

Horrible Bosses (2011)

If you’ve ever had a boss that made your life miserable you’ll appreciate this film. Jason Bateman, Charlie Day, Jason Sudeikis and Steve Wiebe deliver the humor under the direction of Seth Gordon. Three buddies have finally had enough of the abuse. They put together the plan to remove their life-wrecking bosses from this world in this hilarious take on how to commit murder for the betterment of all concerned.

Best in Show (2000)

This movie is hands down my favorite mockumentary of all time.  Christopher Guest absolutely nailed it as director of a film that explores an eclectic (to say the least) group of people who are preparing for an annual dog show.  Whether or not dog people are like this in real life is up to interpretation but I have to believe that at least some of this is spot on.  Brilliant movie.

Dodgeball: A True Underdog Story (2004)

Vince Vaughn is the real hero who considers bailing on the dodgeball team that has a lot riding on the final game. Ben Stiller is the bully who thinks he owns the world and everyone in it. His team is stiff competition, but the stakes are the local gym that means so much to Vaughn and his team. If they lose, Stiller and his team take possession and turn it into a corporate health fitness club as a part of a larger chain.

This is The End (2013)

This is The End is chock full of goodies. If you haven’t watched it a couple of times, the unspoken message of the plot is about consumer culture, its homogenization and finding yourself enticed to accept a new, powerful and possibly shadowy show of force that has the capacity to change what you now know and accept as the status-quo. For those who aren’t really looking for a deeper meaning beyond the entertainment, it’s the story of how time, life events and distance can interrupt friendships. Gary King gathers his crew of buddies from the old days back to their hometown to engage in the epic pub crawl. They proceed with getting hammered and trying to find their way to the last leg of the journey, the World’s End pub. The journey helps them to reconcile yesterday with the present, but turns into a “battle for mankind.”

Role Models

People always forget about this one.  Never underestimate Paul Rudd and Seann William Scott as a duo.  This movie had tons of laughs and was actually kind of a meaningful story when you really get down to it.  Personally I think it’s the kids that make this movie so hilarious.  That and Jane Lynch.  This is before she was so cocky and annoying.




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