Most Hilarious Comedies Of All Time

Comedy is subjective, it’s whatever makes one person laugh. This varies from person to person. However, there are some comedy films that most everyone finds hilarious. These are some of the funniest films of all time.

Superbad (2007)

Superbad is a coming of age buddy comedy written by Seth Rogan and Evan Goldberg. This is one of the movies that propelled Michael Cera and Jonah Hill to superstardom with how well-received it was. The film details the adventures of a pair of teen best friends (played by Hill and Cera), as they attempt to lose their virginity before graduating from high school. Of course, their mission is a lot more difficult than they initially thought. It’s considered one of the best comedies of the 2000s.

Tommy Boy (1995)

Chris Farley wasn’t well-known for making high-quality films, but Tommy Boy was certainly a gem on par with most of his sketch comedy. The film features the hapless heir to a break pad company desperately struggling to keep his company afloat. Of course, his dimwittedness makes this incredibly difficult.

The Blues Brothers (1980)

The Blues Brothers stars John Bellushi and Dan Aykroyd in their prime. Based on the SNL sketch of the same name (created by their actors), the film focuses on the titular Blues Brothers as they attempt to stop the orphanage they were raised in from being shut down. In order to do this, they need to raise $5,000 worth of property taxes. And, of course, the brothers attempt to raise the money the only way they know how: by putting on a show. The film was deemed culturally significant enough to be preserved in the National Film Registry in the Library of Congress.

Dr. Strangelove (1964)

Dr. Strangelove is a blacker comedy than the other films on this list. It’s a Cold War film that features the possible extinction of the human race by nuclear apocalypse. Yet, it still manages to keep the audience engaged and laughing. Probably because of the heavier films, this one still manages to remain relevant in the present day.

Raising Arizona (1987)

People are already familiar with Nicholas Cage’s larger than life performances, so they’d likely lend themselves well to comedy as well as drama. Raising Arizona is the first Coen Brothers film to get mass recognition, and it only makes sense, given how funny it is. The film features career criminal “Hi” McDunnough (Cage) and police officer Ed (Holly Hunter) as a married couple looking to have children. However, as Ed is infertile and they can’t adopt, they decide to kidnap one from the local business magnate, Nathan Arizona (Trey Wilson).

Planes, Trains, And Automobiles (1987)

Many road trip comedy films use this film as a base for their plot. Planes, Trains, and Automobiles features Steven Martin and John Candy as Neal Page and Del Griffith respectively. Page is an advertising executive trying to make it home for Thanksgiving. Of course, on his trip back, everything goes wrong and he finds himself constantly running into Griffith, a shower curtain ring salesman. To make things even worse, the two don’t exactly see eye to eye.

Office Space (1999)

Office Space may have tanked at the box office, but found new life on home video. It’s a real gut buster, and relatable, as everyone’s worked a job they hate before. The film features Ron Livingston as Peter Gibbons as he tries to find fulfillment working at his dingy office job under a boss that he despises. And, after becoming hypnotized to relax more, he begins to find what he’s looking for. It’s almost therapeutic watching some of the characters act the way they do.

Anchorman (2004)

Everyone knows about Anchorman. Even people that haven’t seen the movie know about Anchorman. It’s most well-known scenes likely include the parking lot brawl between all the different news stations and the “that escalated quickly” meme. The film features Ron Burgundy, played by Will Ferrell, and his news team as they butt heads with their newest coworker, a woman named Veronica Corningstone (Christina Applegate). The film’s considered one of the greatest comedies of all time by Bravo, Time Out, The Rolling Stones, and Empire. A sequel was also made in 2013, which kept a lot of the hilarity of the first.

Step Brothers (2008)

Another Will Ferrell comedy, this one features Ferrell and John C. Reilly as childish adults that still live at home. When their parents get married, the two are forced to live together. Initially hateful towards one another, they soon grow to love and respect each other. On top of that, it features the two brothers learning to live on their own and be actual adults.

The 40-Year Old Virgin (2005)

This is the movie that made Steve Carrell a star. Carrell plays Andy Stitzer, a man who, as one could tell from the title, is a 40-year-old virgin. It features Andy’s attempts to not only lose his virginity, but to also find love, which he seemingly does after meeting Trish Piedmont (played by Katherine Keener). Both Carrell and Keener received accolades and high praise for their performances in the film.

A Fish Called Wanda (1988)

This is one of the highest-rated comedies of all time. A Fish Called Wanda featured a pair of con artists, Wanda Gershwitz (Jamie Lee Curtis) and Otto West (Kevin Kline) in their attempts to steal a large sum of diamonds from the thieves they were supposedly helping. However, the diamonds were hidden in an unexpected location, and, hoping to find their location, Wanda attempts to seduce the barrister of the man she double-crossed. The film features a stellar cast, including famous comedic actor John Cleese as Archie Leach.

This is probably the only film on this list that uses elements from real life on the list. While the film has a centralized plot, most of it features the titular character of Borat (Sasha Baron Cohen) interviewing actual Americans that think he’s legitimately a foreigner. Cohen has a certain skill that allows him to disappear into his roles and leave him unrecognizable, so it’s no surprise people were fooled. The general plot of the film involves Borat, a Kazakhstani journalist as he attempts to make a documentary about the US. A sequel film, using a similar premise, was released in 2020.

There’s Something About Mary (1998)

There really does just seem to be something about Mary, at least while watching this film. Mary (Cameron Diaz) is an attractive young woman that multiple men lie to and obsess over her. Her multiple suitors use every possible method to try to win her heart, even after only meeting her one time. It’s a fun ride, that really makes you wonder how all of these men have the same reaction when all she does is walk and talk.

The Big Lebowski (1998)

It might take a few rewatches to fully appreciate the film, but it’s become a cult classic for a reason. The Big Lebowski is about a man named Jeffrey “The Dude” Lebowski (played by Jeff Bridges). Although, the title of the film refers to a much richer man named Jeffrey “Big” Lebowski (David Huddleston). The impetus for the plot is when The Dude is attacked in his home by enforcers looking to collect money from “Big” but enter the wrong house. Saying “hijinks ensue” doesn’t exactly do the wild ride that occurs justice.

The Jerk (1979)

This is certainly an odd one. The Jerk has several ups and downs for its protagonist, Navin R. Johnson (played by Steven Martin). The man was adopted and raised by a black family and he goes off on his own to St. Louis to become a blues performer. While on his journey, he gets a dog, someone tries to randomly assassinate him, and he even falls in love. It’s certainly a wild ride that a normal plot synopsis can’t do justice.

The Naked Gun (1988)

It’s not uncommon that a film based off of a canceled television is created. The Naked Gun is based off of the television series Police Squad! which only ever had six episodes. This film details Lieutenant Frank Drebin (Leslie Nielsen) and his attempts to prevent the enemies of America from assassinating the Queen of England during her visit to the US in Los Angeles. It’s as ridiculous as it sounds, and that’s what makes it such a fun ride.

Dumb and Dumber (1994)

This one’s a little bit more polarizing, as the characters can be a bit too much for some moviegoers. Jim Carey plays Lloyd Christmas and Jeff Daniels is Harry Dunne in this ridiculous misadventure. Lloyd falls in love with a woman while driving her to the airport and attempts to return her briefcase to her when she leaves it in the terminal. However, it’s soon revealed that the briefcase contains ransom money for her husband and a pair of thugs follow Lloyd and Harry while they’re on their mission.

Monty Python’s Life of Brian (1979)

Of all the Monty Python films, this one was the most polarizing. Not so much because it wasn’t funny, but because of the portrayal of Christianity. The movie is about a man named Brian (Graham Chapman), who is the next-door neighbor of Jesus. Being born on the same day as him leads to people mistaking him for the Messiah. Although, all Brian wants to do is live his life. The film has the same brand of wacky comedy the Monty Python crew is known for, just with a slight religious twist.

This Is Spinal Tap (1984)

Another mockumentary, this one tells the story of the heavy metal band Spinal Tap, which is struggling to maintain relevance (or even gain it). The band members are competent, but poor musicians, and it’s just a fun watch from start to finish. This is Spinal Tap was such a phenomena it invented the term “going up to 11”. One of the songs by the band even was played in the video game Lego Rock Band.

Caddyshack (1980)

Caddyshack features an all-star cast and one of the most ridiculous scenarios possible on a golf course. It involves a team golfing match that will essentially determine the fate of a country club. Meanwhile, Bill Murray plays Carl Spackler, whose only goal is to kill a gopher that’s been living on the premises; by any means necessary.

Young Frankenstein (1974)

This is one of the greatest films made by the combination of Mel Brooks and the late, great Gene Wilder. Young Frankenstein is a sort of sequel/parody hybrid, telling the story of Frederick Frankenstein as he attempts to recreate his grandfather’s work in Transylvania. There are many references to the old films as well as some jokes you may have to look up to understand. Regardless, the whole film’s a riot. It was even adapted into a musical.

Animal House (1978)

The frat house film that all fray house films derive their plots from. National Lampoon’s Animal House is possibly the most famous film made by the minds that created the National Lampoon magazine. It’s about possibly the most disruptive fraternity in the world. The members have incredibly poor grades, worse morals, and are constantly on the verge of having their fraternity shut down. Yet, for some reason, you root for them over everyone else in the film. Above anything else, this film is just fun.

Monty Python And The Holy Grail (1975)

Now this is the quintessential Monty Python film. If you wanted to distill everything that makes Monty Python funny, then you’d just have this movie to look at. A twist on the Arthurian Legends, it details King Arthur’s journey on his way to find the Holy Grail. However, of course, it’s not that simple. King Arthur and his Knights of the Round Table are forced to contend with hostile knights, Frenchmen (in England), magical beasts, and, for some reason, a wedding. It’s very rare to see a comedy film where basically every joke lands.

Blazing Saddles (1974)

This could be the greatest Western film of all time. In all seriousness, Blazing Saddles is potentially the greatest film that Mel Brooks has created. This satirical look on the Western genre details a criminal mastermind’s plan to build a railroad through a town. In order to help his plans, he sends a black sheriff (Cleavon Little) so that the racist townspeople won’t accept him and hasten their destruction. Yet, the new sheriff and his deputy, the Waco Kid (Gene Wilder) manage to get the townspeople to change their ways.

Airplane (1980)

Did you know that Airplane is actually a parody of the airplane disaster film genre? It doesn’t matter if you didn’t, this movie is hilarious without that knowledge. As with Blazing Saddles and The Holy Grail, this is a film stooped in zaniness and comedy that never fails to be entertaining. The film features a former air force pilot as he attempts to win back his flight attendant girlfriend, only for the pilot and co-pilot of the plane they’re on to suddenly fall ill. Will people dropping left and right from an unexpected illness, it becomes all the more important that they land the plane before people start dying. With jokes at the very beginning with the tail fin of the plane erupting from the clouds as the Jaws music plays in the background, and an entire line of people telling a woman to “get ahold of herself”, it’s a laugh riot that absolutely holds up today.