#25. Adventureland
This movie has it all! Adventureland can be hardly defined as a comedy, as it’s actually a mix of drama, romance, and a comedy! This 2009 movie is set in the summer of 1987 and it pays tribute to many cheesy teenage movies filmed in the ’80s.
The film is starred by Bill Hader, Kristen Stewart, and Jessie Eisenberg. If you ask me, Hader’s character, Bobby, is the funniest of all, but Stewart will definitely make you laugh with her typical ironic and moody character. All three play a group of friends who meet in a local amusement park, and that’s when their relationship and all the fun begins.
#24. Heathers
Heathers managed to turn the typical silly teenage movie into a murder, mystery and suicide-themed jewel. It tells the story of three girls all called Heather, who are the most popular and hated students in their high school. One day, the most intelligent Heather of the group teams up with a sociopath to get rid of the cool kids and get her reputation back. I won’t spoil the rest, watch it and find out!
This dark comedy was directed by Michael Lehmann and written by Daniel Waters and is starred by Winona Ryder and Christian Slater. Despite not having been a major box office success, Heathers grew up to be a cult film for every teenager!
#23.Trading Places
Sometimes defined as the modern Mark Twain, Trading Places features two of the greatest comedy kings of all time, Eddie Murphy and Dan Aykroyd. You should know that after this movie hit the theaters, Murphy‘s career took off. Despite being the oldest film on this list, it is definitely a must-see and you shouldn’t miss it!
This comedy film was directed by John Landis, and other than Murphy and Aykroyd, it features Ralph Bellamy, Don Ameche, Denholm Elliott, and Jamie Lee Curtis. The story revolves around a homeless guy, played by Murphy, and a commodities broker, who unknowingly ends up being part of a bet between two callous millionaires. Be ready to be at the edge of your seat at all times!
#22. I Love You, Man
I Love You, Man features Paul Rudd and Jason Segel, and let’s face it: anything that involves those two is guaranteed fun! Their chemistry on-screen goes back to Forgetting Sarah Marshall and Knocked Up and this time they nailed it too. So don’t think twice and watch this film while enjoying some popcorn on the sofa! Can you think of a better plan?
Released in 2009, the film was directed by John Hamburg and revolves around a friendless man who is about to marry and wants to find himself a best man. With such an aim in mind, he has to go on a series of man-dates to meet the perfect best man. However, things start to get ugly when tension arises between his BFF and his fiancée. Will this man manage to settle the difference between them and live happily ever after?
#21. Burn After Reading
A film featuring a cast of the sort can never be bad! The Coen Brothers, Brad Pitt, Frances McDormand, George Clooney, Brad Bitt, J.K. Simmons, Richard Jenkins, and Tilda Swinton got together for this black comedy with some crime and mistery. Burn After Reading is certainly a must-see for every comedy lover!
It was written, produced, edited, and directed by Joel and Ethan Coen. It tells the story of two shady gym employees who happen to find a disk from the CIA that contains mysterious information. They try to extort money from the person who lost the disk but nothing goes the way they planned, obviously. The film is guaranteed laughter!
#20. Goon
This sports comedy is far one of the best things Seann William Scott has done apart from Stiffler. Far from being a mainstream hit, Goon has a lot to offer to its viewers: action, slapstick humor and a cast featuring many great comedy actors of the like of Jay Baruchel. Give Goon a shot, you won’t regret it!
The film was directed by Michael Dowse and written by Jay Baruchel and Evan Goldberg. It tells the story of a bouncer whose intelligent family labeled as an outcast, but against all odds, he manages to become a semi-pro hockey legend. Be ready to see Seann William Scott beating everybody that stands in his way for glory!
#19. Forgetting Sarah Marshall
This romantic comedy has Jason Segel as the main character along with an incredible cast, including A-list stars like Kristen Bell, Mila Kunis, and Russell Brand. No wonder the film is insanely rewatchable! A lot of penis jokes, a vulnerable guy trying to get over his ex, and many other bizarre situations make this film pure comedic gold!
The film was directed by Nicholas Stoller. It tells the story of Peter (played by Segel), a man who recently broke up with his TV star girlfriend (Bell), and to deal with the break up he decides to go on holiday to a resort in Hawaii. But what Peter doesn’t know is that Sarah is traveling to the same place with her brand new boyfriend (Brand). The rest is history!
#18. Walk Hard: The Dewey Cox Story
Walk Hard: The Dewey Cox Story is a huge parody of what is presumed to be Johny Cash’s life. It makes fun of movies who tend to retell the lives of past musicians. The movie’s amazing cast features actors of the like of Jenna Fischer, Tim Meadows, Kristen Wiig, Craig Robinson, Jane Lynch, and Judd Apatow.
This movie was directed by Jake Kasdan. It tells the story of Dewey Cox who accidentally cuts his brother in half and because of this traumatic experience he loses his sense of smell. However, Dewey overcomes adversity and ends up becoming a huge rock and roll musician. Comedy, drama and romance, everything in one film!
#17. The Truman Show
Starring Jim Carrey, one of the best comedy actors of all time, The Truman Show is a film that every movie buff should watch at least once. Like every other Carrey film, it is full of complex, strange and bizarre characters.
This sci-fi satire was directed by Peter Weir. The story revolves around Truman Burbank (Carrey), an insurance salesman who was adopted and raised by a corporation that turns his life into a TV show. After noticing some unusual events, Truman becomes aware that he is part of a show and tries to escape. Will he manage to do so? I promise I won’t spoil, watch the film and find out!
#16. Bad Santa
In Bad Santa, Billy Bob Thorton portrays an anti-hero version of Santa and it turns out to be more of a black comedy than a regular one! Even though the film was released during the Christmas season, it can be enjoyed at any time of the year! So are you ready for this unusual holiday classic?
The film was directed by Terry Zwigoff and written by Glenn Ficarra. It tells the story of conman Billy Bob Thorton and his partner Tony Cox, who plan to work as Santa and his little helper in a mall to rob all the department stores on Christmas Eve. Of course, things don’t turn out the way they planned, especially after Santa becomes friends with a deeply troubled kid.
#15. Nacho Libre
Without a doubt, Nacho Libre is one of the most bizarre films out there. After all, can you think of anything weirder than a clumsy romp moving around a ring? Even though it’s not the greatest cinematic masterpiece ever, it makes for a perfect Friday night plan.
The story revolves around a Mexican monk, Jack Black, who follows his dream to become a Luchador or Mexican Wrestler. Shockingly, this film is loosely based on a true story, as Fray Tormenta was a real catholic priest who wrestled for 25 years as a masked luchador to support an orphanage. I bet you didn’t see that coming, right?
#14. Shrek
If you were trapped inside a tower just like in the fairy tales, you wouldn’t expect to be rescued by and fall in love with a giant ogre, right? Although Shrek is not the usual fairy tale prince, he is certainly one of the most beloved and hilarious characters in the history of animation!
Directed by Andrew Adamson and Vicky Jenson, this film tells the story of a grumpy ogre whose swamp is being invaded by fairytale creatures, after they were exiled from their homes by a mean lord. Annoyed by all these creatures, Shrek goes on a quest to rescue Princess Fiona from the evil lord to get his swamp back. Mike Myers and Eddie Murphy are the lead voice actors, so what’s not to like?
#13. Wet Hot American Summer
Even though this film was a huge commercial failure, it became a cult film over the years. Wet Hot American Summer features Bradley Cooper in his film debut, as well as other top-notch comedians, like Ken Marino and Amy Poehler among many other top-notch comedians. What else can you ask for’
Directed by David Waine, this satirical comedy tells the story of a group of counselors and the adventures they embark on the last day of camp. Basically, they all want to seize their last opportunity of finding a summer fling before summer at Camp Firewood ends. Ending in a talent show, this film is a must-see for teens and adults alike!
#12. Beerfest
Is beer one of your favorite drinks? Would you like to take part in a beer-drinking competition but never had the chance? Well, at least you can have some fun watching this film since it comprises everything listed above. Beerfest was directed by Jay Chandrasekhar and is starred by the comedy troupe Broken Lizard (Kevin Heffernan, Steve Lemme, Paul Soter, and Erik Stolhanske).
The story revolves around two brothers whose grandfather dies, and as a family tradition, they must go to Munich during Oktoberfest to spread his ashes. Everything turns upside down while taking part in a beer drinking competition when they discover that they are related to the one who runs the whole event!
#11. Scary Movie
Are you a fan of comedy and horror films? Well, the Scary Movie saga is the perfect match for you! Created and developed by the Wayans Family, the saga comprises five parody films of the most well-known horror movies of all time.
Even though the whole saga is worth a watch, If I had to choose only one, I would go with the first. Starred by top-notch actresses such as Anna Faris and Carmen Electra, the film is a parody of Scream and I Know What You Did Last Summer, though it also makes fun of Scream 2, The Sixth Sense, The Blair Witch Project, The Shinning and The Usual Suspects.
#10. Adventures In Babysitting
Adventures in Babysitting is a typical 80s film that you just can’t miss. A car chase, a gang fight, and even an armed robbery, everything in this cult classic scream 80s! It is starred by a young Elizabeth Shue and the cast features Anthony Rapp and Keith Coogan. Teenage films are always the best, and this one is no exception.
Released in 1987, the film was written by David Simkins and directed by Chris Columbus. A normal babysitting night turns out to be much more of what a babysitter, Elizabeth Shue, had bargained! She is helpless and has to battle all around town with the kids she is supposed to be looking after. It is not only a funny movie but also exciting, as everything goes wrong!
#9. Talladega Nights: The Ballad Of Ricky Bobby
It is safe to say that Talladega Nights is one of the most hilarious comedy films out there. This should come as no surprise, as it is starred by one of the greatest comedy minds of these past generations, Will Ferrell, and it was written by the most famous comedy writers of these past decades, Judd Apatow. Ferrell plays the role of a NASCAR driver with a quite interesting southern accent, which many people claim sounds exactly like George Bush!
This sports comedy film was directed by Adam McKay and also features John C. Reilly, Sacha Baron Cohen, Gary Cole, Michael Clarke Duncan, Leslie Bibb, Jane Lynch, and Amy Adams. It tells the story of Ricky Bobby, a NASCAR driver who manages to stay at the top of ranks by making a pact with his best friend. However, Bobby has to prove his talent when a professional French driver appears. Will he continue being the best racer of all? Watch it and find it out!
#8. Hot Fuzz
Sure, all the films on this list are funny, but what’s special about Hot Fuzz is that it manages to make us laugh by adding a comedic touch to all the gore scenes. The film was starred by Nick Frost and Simon Pegg and directed by Edgar Wright, and only they could make such a hilarious cop film!
The film tells the story of a London police officer who is transferred to a little town with a low crime rate, but as soon as he moves in, people start dying in the strangest ways. Nicholas Angel (played by Pegg) believes that the victims were murdered and he starts investigating these cases. Full of gore and some black humor, it is certainly a film worth watching!
#7. The Waterboy
Whereas The Waterboy can’t be described as an Academy award-winning movie, it certainly made Adam Sandler rise to fame! This movie is as ridiculous as it gets, and let me tell you one thing: you won’t be looking at water or Gatorade in the same way after watching it!
This sports comedy film was directed by Frank Coraci. It features not only Sandler but also Kathy Bates, Fairuza Balk, Henry Winkler, Jerry Reed, Larry Gilliard, Jr., Blake Clark, Peter Dante, and Jonathan Loughran. The story revolves around a waterboy (Sandler) who is part of a college team and one day suddenly discovers that he has a unique tackling ability!
#6. Ghostbusters
The iconic song of Ghostbusters can sure give you the chills and it should definitely be part of every Halloween party! This movie was a huge hit in 1984 and to this day it is regarded as one of the funniest mystery films ever. Don’t be misled by the title, Ghostbusters is far from being a horror film and its suitable for all ages.
This fantasy comedy film was directed by Ivan Reitman and as a result of its success, it was followed by a sequel in 1989. The story revolves around three unemployed parapsychology professors who decide to set up a ghost removal service in the city of New York. Its cast features Bill Murray, Peter Venkman, Raymond Stantz, and Egon Spengler.
#5. Tropic Thunder
This satirical action comedy film was directed by Ben Stiller and it stars Stiller, Jack Black, Robert Downey Jr., Jay Baruchel, and Brandon T. Jackson. Although Tropic Thunder is meant to be a parody of a war movie, the truth is that in some parts it seems more of a war movie than a comedy!
The film tells the story of a group of actors who are left in the middle of the jungle by a movie director to film a war movie, but what the cast was never told is that they would have to rely on their own skills to survive a real war! Yikes!
#4. Bring It On
Mean Girls wasn’t the first teenage comedy about the troubles faced by popular high school girls! In Bring It On, a cheerleading squad must compete in a national championship, but as you can imagine, everything goes wrong! It comprises all the typical teen stereotypes – such as the popular girl, the shallow one, and the nerd – and it’s definitely one of the funniest teen films ever!
The new captain of the squad, Kirsten Dunst, discovers that the former captain had stolen all their best routines from another less popular school. But problems begin to arise when they find out they have to compete with them at the annual cheerleading championship. Are you ready to enjoy some jaw-dropping athletic performances? Prepare your popcorn and be ready to see cheerleaders flying through the air!
#3. Inglorious Basterds
This Tarantino movie is no ordinary comedy. No matter how impossible it sounds, this war movie manages to portray Hitler and the Second World War with a comedy touch. But above all, Inglorious Basterds includes brilliant performances of many A-list stars, including Brad Pitt, Michael Fassbender, Christoph Waltz, and Diane Krueger.
The script of the film was written in 1998 but filmed in 2008 in France and Germany. It tells the story of how two groups of people plan to assassinate Nazi Germany’s leadership. One group is headed by a French girl called Shoshanna, while the other is led by First Lieutenant Aldo Rain. Inglorious Basterds has it all: an incredible cast, an amazing director and even a cameo of Eli Roth as Donny ‘The Bear Jew’ Donowitz!
#2.The 40-Year-Old Virgin
No need to explain what The 40-Year-Old Virgin is about, right? As its title suggests, it’s the story of a man who had never had sex. Starred by the great Steve Carell, this 2005 movie has nothing to waste. The 40-year-old virgin faces the most awkward moments in bed and is given the most awful advice from his coworkers, generating some of the most absurd and comedic situations you can think of.
This sex comedy was directed by Judd Apatow, and it was nothing less than his directional debut! Along with Carell, the cast features Catherine Keener and Paul Rudd. The story revolves around Andy Stitzer, Carell, who is the perfect definition of a nerd and whose friends try to help him lose his virginity. But things start to get interesting when he meets a single mother!
#1. Meet The Parents
One of the worst things in a relationship is meeting the parents for the first time, don’t you think so? Well, in the classic film Meet the Parents, poor Ben Stiller has to face his worst nightmares upon meeting their in-laws. Not only will you laugh at Stiller’s neurotic behavior, but also at many of the most bizarre situations you can think of, such as a cat flushing a toilet!
This film was written by Jim Herzfeld and John Hamburg and directed by Jay Roach. The film follows the steps of a male nurse (Stiller) who is meeting his girlfriend’s parents for the first time before proposing. His father-in-law (Robert De Niro) is a retired CIA operator who tries to sabotage Stiller from getting married to his daughter. Along with an incredible intelligent script and a top-notch cast, this film had to be at the top of this list!