There are several movies that are so unique and creative that they break the the best movies of all time are ed for their unusual yet refreshing takes on the usual stereotypes and tropes that are commonly found in comedy titles, many of which stick in audiences’ minds for years after their initial releases. Over the years, there have been all manner of wild and wacky comedy movies in the world of cinema, but certain eras stand out more than others.

There are loads of weird comedy movies from the 2000s, for example. These films bring something new to the table, and regardless of whether they reinvent comedy’s biggest clichés or simply present them in a new way, there’s no doubt that they’re mold-breakers.

10 Palm Springs (2020)

A New Twist On A Time Loop Movie

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Palm Springs
Release Date
July 10, 2020
Runtime
90 minutes
Director
Max Barbakow

WHERE TO WATCH

Streaming

Palm Springs is a sci-fi comedy film that sees two strangers, Nyles and Sarah, who meet at a wedding reception and, after heading off for a night of debauchery, are tossed into a strange vortex that keeps them date locked in November 9th with no perceivable way out. Nyles and Sarah bond while trying to find an escape from the odd time loop as the truth behind the vortex slowly unravels.

Writers
Andy Siara

Palm Springs is a great time loop movie that isn’t Groundhog Day, by taking the concept and putting a spin on it that is both unique, yet still takes inspiration from the classic title. The movie follows Cristin Milioti as Sarah, whose depressing day at her sister’s wedding takes a turn for the worse when she meets Andy Samberg’s Nyles. Experiencing the same day over and over again naturally sets up comedic situations, but the true humor of Palm Springs comes from the relationships that form.

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Sarah and Nyles’ connection is realistic, which makes it easier to invest in the characters, and it’s hilarious to watch them progress from strangers to friends, and eventually, fall for one another. Reliving the same day is tough enough, but for Sarah, it’s possibly the worst day that could ever be picked for her. Palm Springs is fascinating because it looks at what happens if more than one person is in the time loop, all of whom get stuck at different points, and is an overall brilliantly funny watch.

9 Tucker & Dale Vs. Evil (2010)

A Horrific Misunderstanding

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Tucker & Dale vs. Evil
Release Date
September 30, 2011
Runtime
89 minutes
Director
Eli Craig
  • Headshot Of Tyler Labine
    Tyler Labine
  • Headshot oF Katrina Bowden
    Katrina Bowden

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Tucker & Dale vs. Evil is a 2010 horror/comedy film starring Tyler Labine and Alan Tudyk. Labine and Tudyk play a dynamic hillbilly duo that is mistaken for killers when college students around them continue to accidentally kill themselves in gruesome ways. Tucker & Dale vs. Evil marks director Eli Craig's feature-length directorial debut.

Writers
Morgan Jurgenson, Eli Craig

Tucker & Dale vs. Evil is a horror movie parody from the early 2000s, that focuses on a group of college students who mistake the titular characters for violent killers. Alan Tudyk and Tyler Labine’s respective performances as Tucker and Dale are phenomenal, and it’s comical to see them portray a pair of misunderstood hillbillies who mean no harm. Tucker & Dale vs. Evil takes several intriguing horror tropes and subverts them, which results in all manner of comical situations.

The absurdity of the film is fantastic, but Tucker & Dale vs. Evil also does horror well, too.

Miscommunication in the comedy genre is the easiest way to get laughs, but Tucker & Dale vs. Evil’s use of it doesn’t feel overused. The absurdity of the film is fantastic, but Tucker & Dale vs. Evil also does horror well, too. In fact, there are several references to other horror movies. Despite being a parody, there are some genuinely scary moments, but it doesn’t dampen the comedic moments, and vice versa. Tucker & Dale vs. Evil is one of the most entertaining horror movies ever made, and an underappreciated title in general.

8 Don't Look Up (2021)

A Satirical Yet Truthful Look At The End Of The World

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Don't Look Up
Release Date
December 10, 2021
Runtime
145 minutes
Director
Adam McKay

WHERE TO WATCH

Streaming

Don't Look Up follows two astronomers (Leonardo DiCaprio and Jennifer Lawrence) desperately trying to warn humanity about an approaching comet that they believe could wipe out all life on Earth. When the President (Meryl Streep) and her son (Jonah Hill) ignore their warnings, they embark on a media tour to enlighten the public, earning the ire of the global populace who refuse to believe in the danger. Meanwhile, an eccentric billionaire (Mark Rylance) begins to fund an emergency colonization mission to take humanity out among the stars. 

Writers
Adam McKay, David Sirota

Don’t Look Up doesn’t initially appear to be a comedy, but that’s because of the film’s particular sense of humor. The rather dark, satirical movie stars Leonardo DiCaprio as astronomy professor Dr. Randall Mindy and Jennifer Lawrence as astronomy PHD candidate Kate Dibiasky, who discover a comet that is set to cause an extinction-level event. Don’t Look Up mocks modern-day politics, those who refuse to believe scientific fact, and the media in a brutal (and unfortunately realistic) way.

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Don’t Look Up’s cast also includes Meryl Streep as the President, who provides an excellent performance as the deluded and scandalous politician. The deep dive into the intricacies of human nature is captivating, and while the film’s humor is rather blunt and quite dry, it only pushes the overall message further. Even though Don’t Look Up focuses primarily on the disaster at hand and society in general, the movie’s comedic direction is definitely unique and creative.

7 Spaceballs (1987)

A Groundbreaking Sci-Fi Parody

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Spaceballs
Release Date
June 24, 1987
Runtime
96 minutes
Director
Mel Brooks
  • Cast Placeholder Image
    Mel Brooks
    President Skroob / Yogurt
  • Cast Placeholder Image
    John Candy
    Barf

WHERE TO WATCH

Spaceballs is a 1987 comedic science fiction film directed by Mel Brooks. It follows Lone Starr and his sidekick as they confront the villainous Dark Helmet, who schemes to kidnap Princess Vespa and steal her planet's air. They encounter Yogurt, who introduces them to the mystical power known as "The Schwartz."

Writers
Mel Brooks, Ronny Graham, Thomas Meehan

Spaceballs is one of the best '80s sci-fi movies ever, and a hilarious parody of other titles from the genre, such as the original Star Wars trilogy and 2001: A Space Odyssey. The film stars titans of the industry like Rick Moranis, Joan Rivers, and Mel Brooks in an array of hilarious sci-fi parody characters. Despite the fact Spaceballs only exists because of other huge hits in the sci-fi genre, the movie also has its own cult following, and continues to grow in popularity with every ing year.

Spaceballs is a standout film in both comedy and science fiction, and it heavily relies on slapstick comedy and constantly mocks various sci-fi stereotypes and tropes. In fact, there are so many hilarious quotes in Spaceballs that there’s barely any time to stop laughing over one before another crops up. Spaceballs will forever be ed for breaking the parody movie mold, and I can’t wait to see what the Spaceballs 2 will mock over 30 years after the original’s release.

6 Monty Python And The Holy Grail (1975)

The British Troupe's Hilarious And Historical Tale

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Monty Python and the Holy Grail
Release Date
May 25, 1975
Runtime
91 minutes
Director
Terry Jones, Terry Gilliam
  • Headhsot Of Michael Palin
    Michael Palin
  • headshot Of John Cleese
    John Cleese

WHERE TO WATCH

Streaming
RENT
Writers
Terry Jones, Graham Chapman, Terry Gilliam, Eric Idle, Michael Palin, John Cleese

The Monty Python movies are some of the best comedy titles in cinematic history, but the crowning jewel of the bunch is easily Monty Python and the Holy Grail. The comical interpretation of King Arthur and his knights’ journey to locate the Holy Grail is a memorable one. The troupe's first feature-length movie is full of iconic moments, like the Black Knight fight and the invisible horses in the opening shot, many of which are fondly ed by audiences of various generations.

The most notable thing about Monty Python and the Holy Grail’s humor, however, is how meta it is. The fourth-wall-breaking jokes are astounding and crucial to the film’s success. Even though Monty Python and the Holy Grail is far from historically accurate at times, that’s kind of the point of it. Without the Monty Python group, future historical parody titles like Blackadder and The Princess Bride wouldn’t be as popular as they are.

5 Wet Hot American Summer (2001)

Not Your Average Camp Experience

Wet Hot American Summer Movie Poster

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Wet Hot American Summer
Release Date
July 27, 2001
Runtime
97 Minutes
Director
David Wain

WHERE TO WATCH

Wet Hot American Summer is a zany comedy that captures the absurd and hilarious antics of camp counselors on the last day of summer camp in 1981. At Camp Firewood, a quirky group of young adults grapples with the challenges of teenage love, friendships, and the pressure to conclude the summer with a bang. Amidst a backdrop of ridiculous events and over-the-top camp activities, each counselor confronts their own comical dilemmas, aiming to make the most of their final camp hours. 

Writers
Michael Showalter, David Wait
Main Genre
Comedy

I absolutely love the Wet Hot American Summer TV shows, and the original 2001 film sets up the success of the Netflix titles brilliantly. Wet Hot American Summer is one of the best summer camp movies, and features a star-studded cast of actors, including Amy Poehler, Paul Rudd, and Elizabeth Banks. While the story is generally as expected, there are moments that are so random that it’s impossible not to find them funny.

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From a talking can of vegetables to a montage of the teens shooting up drugs in a strange house, Wet Hot American Summer’s sense of humor is completely wild. Wet Hot American Summer’s running gags, nonsensical interactions, satirization of the 1980s, and mocking of comedy tropes are fantastic, and I hope that Netflix will revisit the TV shows in the future.

4 Airplane! (1980)

A Staple Title In Comedy

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Airplane!
Release Date
July 2, 1980
Runtime
88 minutes
Director
Jim Abrahams, David Zucker, Jerry Zucker
  • Cast Placeholder Image
    Kareem Abdul-Jabbar
  • Cast Placeholder Image
    Lloyd Bridges

WHERE TO WATCH

Streaming

Airplane! is a 1980 comedy film directed by Jim Abrahams, David Zucker, and Jerry Zucker. It parodies disaster films, centering on Ted Striker, a former fighter pilot dealing with a fear of flying. When an in-flight emergency strikes, Striker must confront his fears to save the engers and crew. The film stars Robert Hays, Julie Hagerty, and Leslie Nielsen, employing a mix of slapstick humor and rapid-fire jokes.

Writers
Arthur Hailey, Hall Bartlett, John C. Champion, Jim Abrahams, David Zucker, Jerry Zucker

If any movie can be considered the one to originally break the mold, it’s Airplane! Even decades after the film’s release, many audiences of all ages are familiar with Airplane!’s best quotes and ridiculous sense of humor overall. Airplane! parodies the disaster movie genre and follows the pilots, cabin crew, and engers on board a flight to Chicago. Word play is essential to the movie’s comedy, and there’s no film past or present that executed it as well as Airplane! does.

Airplane!’s comic timing is also perfect, and it only adds to the overall surreal comedic tone of the title. Even though some jokes age badly, most of Airplane! still holds up, proving itself to be a timeless classic not only in the comedy genre, but in cinema altogether. The fast pacing, non-stop jokes in every scene, and wacky atmosphere in Airplane! is truly like no other.

3 Ingrid Goes West (2017)

Aubrey Plaza Redefines Uncomforable Humor In This Movie

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Ingrid Goes West
Release Date
August 11, 2017
Director
Matt Spicer
Writers
David Branson Smith, Matt Spicer
  • Headshot Of Billy Magnussen
    Billy Magnussen
  • Headshot of O'Shea Jackson Jr.
    O'Shea Jackson Jr.

Ingrid Goes West is a dark comedy film starring Aubrey Plaza as Ingrid Thorburn, a troubled young woman who becomes obsessed with a social media influencer, Taylor Sloane, played by Elizabeth Olsen. Directed by Matt Spicer, the film explores the impact of social media on mental health and relationships as Ingrid relocates to Los Angeles in an attempt to insinuate herself into Taylor's seemingly perfect life.

Main Genre
Comedy

Ingrid Goes West’s sense of humor is painfully uncomfortable and a little eerie, but it works in the film’s favor, and also establishes an important message about mental health. The movie stars Aubrey Plaza as the lonely titular character, who becomes obsessed with Elizabeth Olsen as influencer Taylor, and the forced friendship that forms between them. Ingrid’s reinvention of herself in order to befriend Taylor is fascinating, and while it’s comical to see her pretend to be a rich socialite-esque figure, it’s also a little haunting.

It’s easy to feel second-hand embarrassment for Ingrid at times, but it’s hard to look away from her, too.

Ingrid Goes West’s dark themes delve into the realities of toxic influencer culture, social media, and loneliness. It’s easy to feel second-hand embarrassment for Ingrid at times, but it’s hard to look away from her, too. Plaza’s comedic timing, ability to beautifully portray twisted characters, and her subtle yet powerful facial expressions are truly fantastic. While you might not be laughing by the very end of Ingrid Goes West, it’s definitely a title that undoubtedly breaks the comedy genre mold.

2 Scott Pilgrim Vs. The World (2010)

Edgar Wright's Hilarious Adaptation Of The Comic Series

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Scott Pilgrim vs. the World
Release Date
August 12, 2010
Runtime
113 minutes
Director
Edgar Wright

WHERE TO WATCH

Based on Lee O'Malley's Scott Pilgrim series of graphic novels, Scott Pilgrim vs. the World follows the titular slacker musician (Michael Cera) as he strives to earn a record deal by winning the Battle of the Bands organized by music mogul Gideon Graves (Jason Schwartzman). After meeting and falling in love with Ramona Flowers (Mary Elizabeth Winstead), Scott learns that he must also defeat her seven evil exes. Chris Evans, Aubrey Plaza, Brandon Routh, Kieran Culkin, Anna Kendrick, and Brie Larson round out the film's star-studded and quirky ensemble. 

Writers
Edgar Wright, Michael Bacall
Main Genre
Action

Scott Pilgrim vs. the World is an iconic title in the worlds of movies, TV, and comic books. Edgar Wright’s 2010 movie stars Michael Cera as Scott Pilgrim, who falls in love with Mary Elizabeth Winstead as quirky cool girl Ramona Flowers, and is tasked with defeating her seven evil exes to win her heart. Scott Pilgrim vs. the World uses a combination of live-action footage and special effects to take the story of a bumbling guitar player and turn him into somewhat of a video game superhero.

Scott Pilgrim vs. the World also has some great and inventive jokes, too. It’s incredibly surreal and meta at times, and the cult classic movie from the 2010s is one of the most notable titles within this strange subgenre of comedy, despite initially being a box office flop. Scott Pilgrim vs. the World is wild and rather absurd, but it’s one that viewers don’t forget quickly, and I’m still disappointed that Scott Pilgrim Takes Off isn’t getting a season 2, but hopefully Netflix will reconsider the anime in the future.

1 Adaptation (2002)

Charlie Kaufman's Strange Meta Movie

Adaptation. - Poster

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Adaptation.
Release Date
December 6, 2002
Runtime
115 Minutes
Director
Spike Jonze

WHERE TO WATCH

Adaptation is a metafictional film directed by Spike Jonze, featuring Nicolas Cage in dual roles as screenwriter Charlie Kaufman and his fictional twin brother Donald. Released in 2002, the film chronicles Kaufman’s struggle to adapt Susan Orlean’s book The Orchid Thief while wrestling with personal and professional crises.

Writers
Susan Orlean, Charlie Kaufman
Main Genre
Comedy

Adaptation is one of the most meta movies of all time, and one that I always find new little details in with every rewatch. The film stars Nicolas Cage in his Oscar-nominated performance as Adaptation’s writer Charlie Kaufman and his fictional twin, Donald. Adaptation strangely jumps between two main stories: Charlie’s struggles with writer's block after he is tasked with, ironically, writing a film adaptation of a book, and Meryl Streep’s Susan Orlean, the author behind The Orchid Thief, and her relationship with Chris Cooper’s John Laroche.

Adaptation’s use of humor is dry and subtle. It’s hard not to cringe at Charlie’s non-stop randiness, as is Orlean’s inappropriate affair with the orchid-stealing Laroche, but it still works. The movie is often confusing at times, but not in a way that makes audiences feel overly ostracized, but the absurdity of it simply makes it funnier. While Adaptation is an odd title in the comedy genre, it’s also thought-provoking and full of intelligent humor.