Though every decade boasts offbeat and unusual additions to the comedy genre, the 2000s have some of the most bizarre comedies in history. While some have aged well and are now considered cult classics, others have not stood the test of time, not just confusing the audience but making them a little uncomfortable. However, even when these projects toe the line between offputting and terrifying, it’s interesting to revisit them and witness how writers and directors were testing the waters in the new millennium and experimenting with style and form.
Some of these are 2000s comedies that barely anyone remembers, as they were critically panned at the time of their release and largely deemed unwatchable. However, just because a comedy has a negative critical reception doesn’t mean it isn’t worth remembering. There’s something exciting about watching a movie that’s unapologetically itself and doesn’t try to pander to the audience. The best way to watch these comedies is to expect to be confused and be willing to suspend your disbelief during the most shocking moments.
You are watching: I Realized The 2000s Was A Strange Time When I Watched These 10 Weird Comedy Movies
10
Freddy Got Fingered (2001)
Directed by Tom Green
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Freddy Got Fingered
R
Comedy
Release Date
April 20, 2001
Runtime
87 minutes
Cast
See All
-
Tom Green
Gord Brody
-
Rip Torn
Jim Brody
-
Marisa Coughlan
Betty
-
Eddie Kaye Thomas
Freddy Brody
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Largely panned and considered a failure at the time of its release, the darkly comic and extreme satire Freddy Got Fingered stars the director, Tom Green. Green plays the protagonist, Gordon, who dreams of having his own cartoon TV series and is frequently put down by his overbearing father. Throughout the story, Freddy Got Fingered sees Gordon come into contact with many outlandish characters, like his love interest, Betty (Marisa Coughlan) and isn’t afraid to make the audience cringe.
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10 Most Rewatchable Comedies From The 2000s
From raunchy stoner comedies to indie teen comedies to hilarious rom-coms, the 2000s had an array of comedy movies that still hold up today.
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3
Though Freddy Got Fingered has become no less strange with time, Green’s dedication to making an unusual and surreal piece of cinema remains impressive. The best way to engage with Freddy Got Fingered is not to expect to laugh, see a coherent series of events, or even find a semblance of story structure. Instead, Freddy Got Fingered should be remembered as a project that was desperate to be unique in a sea of boilerplate comedies, and it certainly achieved that.
|
Title |
Rotten Tomatoes Critic Score |
Rotten Tomatoes Audience Score |
|
Freddy Got Fingered (2001) |
12% |
56% |
9
Kung Pow! Enter The Fist (2002)
Directed by Steve Oedekerk
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Kung Pow: Enter the Fist
PG-13
Comedy
Action
Release Date
January 25, 2002
Runtime
81 minutes
Cast
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-
Steve Oedekerk
The Chosen One
-
Lung Fei
Master Pain (Betty) (archive footage)
-
Leo Lee
Young Master Pain
-
Hsieh Ling-ling
Ling (archive footage)
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Kung Pow! Enter the Fist takes some of the campy and over-the-top aspects of the Hong Kong martial arts genre and parodies them. One of the biggest ways the movie pokes fun at these projects is through the use of exaggeratedly bad voice-over dubbing, which was a common experience for foreigners who followed Hong Kong cinema. Written, directed by, and starring Steve Oedekerk, Kung Pow! Enter the Fist makes some missteps, but it’s clear that Oedekerk loves the genre.
A martial arts comedy movie that doesn’t star Jackie Chan, Kung Pow! Enter the Fist has developed into something of a cult classic, especially for contemporary fans of classic films. The excessive punchlines and extreme humor can be a little too much for audiences, but it ultimately suits the style and tone of Kung Pow! Enter the Fist. Oedekerk’s character, the Chosen One, follows all the rules and tropes typically assigned to the heroes of the martial arts genre with some subversions, like the dubbing and inclusion of archival footage.
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Title |
Rotten Tomatoes Critic Score |
Rotten Tomatoes Audience Score |
|
Kung Pow! Enter the Fist (2002) |
13% |
69% |
8
Shallow Hal (2001)
Directed by Bobby & Peter Farrelly
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Shallow Hal
PG-13
Comedy
Drama
Fantasy
Release Date
November 9, 2001
Runtime
114 Minutes
Cast
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Jack Black
Hal
-
Gwyneth Paltrow
Rosemary
-
Jason Alexander
Mauricio
-
Joe Viterelli
Steve Shanahan
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Gwyneth Paltrow and Jack Black co-star as Rosemary and Hal in Shallow Hal, a fantastical rom-com that has aged poorly. The conceit of Shallow Hal is that Hal falls in love with Rosemary after being hypnotized to see only inner beauty, with the script consistently making cruel jokes about weight and body image. It’s hard to get past the disheartening core of the story, and the concept of how Hal goes on this journey doesn’t make a lot of sense to begin with.
The writers and directors of Shallow Hal might have set out to make the movie with good intentions to communicate the importance of inner beauty, but the result doesn’t come off this way.
Shallow Hal isn’t one of Jack Black’s underrated comedy movies, as it’s likely for the best that this dated farce has been overwhelmingly forgotten about. The writers and directors of Shallow Hal might have set out to make the movie with good intentions to communicate the importance of inner beauty, but the result doesn’t come off this way. Shallow Hal doesn’t make up for its shortcomings with an innovative story structure, leaning into the bizarre premise to make up for the weak narrative.
|
Title |
Rotten Tomatoes Critic Score |
Rotten Tomatoes Audience Score |
|
Shallow Hal (2001) |
49% |
45% |
7
Wet Hot American Summer (2001)
Directed by David Wain
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Wet Hot American Summer
R
Comedy
Romance
Release Date
July 27, 2001
Runtime
97 Minutes
Cast
See All
-
Janeane Garofalo
-
David Hyde Pierce
-
Michael Showalter
-
Marguerite Moreau
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Despite being considered a cult classic and even garnering a 2015 TV reboot, Wet Hot American Summer: First Day of Camp, Wet Hot American Summer is undeniably offbeat. Featuring an all-star cast of comedians from Molly Shannon and Amy Poehler to Ken Marino and Paul Rudd, Wet Hot American Summer works because the actors are so committed to the absurdity of the premise. A play on the summer camp movie and teen comedy genre, Wet Hot American Summer is over-the-top and unbelievable whenever possible.
However, it’s this strangeness that has allowed the comedy to age decently well, giving it a timeless quality with elements that appeal to audiences of all generations. Wet Hot American Summer doesn’t take itself seriously, as the whole cast and crew are aware that there are many elements of the story that make no sense. However, the point of Wet Hot American Summer isn’t to follow a cohesive narrative but to make the viewer laugh and go along for the ride of silliness.
|
Title |
Rotten Tomatoes Critic Score |
Rotten Tomatoes Audience Score |
|
Wet Hot American Summer (2001) |
39% |
75% |
6
Osmosis Jones (2001)
Directed by Bobby & Peter Farrelly
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Osmosis Jones
PG
Animation
Action
Adventure
Release Date
August 10, 2001
Runtime
95 Minutes
Cast
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-
Laurence Fishburne
Thrax
-
Chris Rock
Osmosis Jones
-
David Hyde Pierece
Drix
-
Brandy Norwood
Leah
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The semi-educational comedy animation movie Osmosis Jones has been largely forgotten about. However, revisiting the project from the early 2000s is a reminder of these unique films that expanded upon traditional animation and comedy. The voice cast of Osmosis Jones is particularly notable because it boasts iconic actors like Chris Rock and Laurence Fishburne, with Bill Murray and Molly Shannon appearing in the live-action cast. Osmosis Jones takes the viewer inside the body of a sick man from the perspective of his blood cells.
The titular Osmosis Jones, voiced by Rock, is a white blood cell on a mission to find the root cause of a deadly illness, voiced by Fishburne.
The titular Osmosis Jones, voiced by Rock, is a white blood cell on a mission to find the root cause of a deadly illness, voiced by Fishburne. Though it’s not uncommon for an animated project to anthropomorphize inanimate objects, few have taken the route of Osmosis Jones and used the human body as the setting for an adventure story. Osmosis Jones doesn’t end up being very educational, and some of the humor might go over the heads of its intended audience. However, its premise is unlike any other animated comedy.
|
Title |
Rotten Tomatoes Critic Score |
Rotten Tomatoes Audience Score |
|
Osmosis Jones (2001) |
55% |
42% |
5
Down With Love (2003)
Directed by Peyton Reed
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Down with Love
PG-13
Comedy
Action
Romance
Thriller
Release Date
May 16, 2003
Runtime
101 minutes
Cast
See All
-
Renée Zellweger
Catcher Block
-
Ewan McGregor
Barbara Novak
-
Sarah Paulson
Vikki Hiller
-
David Hyde Pierce
Peter MacMannus
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The early 2000s boast some of the best additions to the romantic comedy genre, and though Down With Love is a little different, it’s worth remembering. Renée Zellweger and Ewan McGregor play the leads in Down With Love, who are modeled after archetypes of the 1960s sex-comedy genre. Heavily stylized and otherworldly, Down With Love might not immediately appeal to audiences unfamiliar with its references, but that doesn’t stop the film from being unapologetically itself.
On the surface, it might seem like Down With Love is just another satirical rom-com, but the film is secretly much more subversive than it originally got credit for. Zellweger and McGregor are hilarious in their roles as Barbara and Catcher. Though Down With Love takes the premise of the farce pretty far, resulting in some unexpected plot twists, the performances keep Down With Love accessible, if absurd. However, Down With Love aims to be absurd in all aspects of the plot, becoming a cult classic in recent years.
|
Title |
Rotten Tomatoes Critic Score |
Rotten Tomatoes Audience Score |
|
Down With Love (2003) |
60% |
62% |
4
Click (2006)
Directed by Frank Coraci
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Click
PG-13
Comedy
Drama
Fantasy
Release Date
June 23, 2006
Runtime
107 minutes
Cast
See All
-
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Adam Sandler
Michael Newman
-
Kate Beckinsale
Donna Newman
-
Christopher Walken
Morty
-
David Hasselhoff
Ammer
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Adam Sandler is well known for starring in some of the most confusing and critically panned comedies of the early 2000s. Click is an interesting addition to his filmography that gets pretty dark by the end of the film. Though Click has an ultimately uplifting ending, it’s a stark warning about how precious time is and holds an ominous morality tale at the heart of the story. Sandler’s character, Michael, gets access to a remote control that can alter time and reality and starts to miss out on his life.
Though Click isn’t the first comedy to grapple with themes of regret and alternate timelines, it isn’t grounded in reality, which makes the narrative hard to grasp.
Throughout Click, it doesn’t take long for Michael to accidentally start missing the big moments and lose his family altogether in a terrifying alternate timeline full of pitfalls and devastation. It’s slightly shocking that Click gets as morbid and intense as it does, ensuring that the audience never forgets this family comedy. Though Click isn’t the first comedy to grapple with themes of regret and alternate timelines, it isn’t grounded in reality, which makes the narrative hard to grasp.
|
Title |
Rotten Tomatoes Critic Score |
Rotten Tomatoes Audience Score |
|
Click (2006) |
34% |
66% |
3
Frequently Asked Questions About Time Travel (2009)
Directed by Gareth Carrivick
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Frequently Asked Questions About Time Travel
PG-13
Comedy
Drama
Romance
Science Fiction
Release Date
April 24, 2009
Runtime
83 minutes
Cast
See All
-
Dean Lennox Kelly
Pete
-
Chris O’Dowd
Ray
-
Marc Wootton
Toby
-
Anna Faris
Cassie
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The incomparable Anna Faris played opposite a trio of would-be time travelers in Frequently Asked Questions About Time Travel, a comedic send-up of the well-worn genre. Movies that blend science fiction and comedy are expected to be a little weird and offbeat. The audience enters these worlds with the intention of suspending their disbelief. Following the three men as they’re caught in a time leak that keeps changing their reality, FAQ About Time Travel revels in its plot, making it hard to predict.
One of the best time travel comedy movies, Frequently Asked Questions About Time Travel, doesn’t have clear-cut rules about how time travel works and the rules of the universe, allowing the movie to run wild. The movie pokes fun at the overly complex narratives of time travel films, getting more intricate and confusing with each loop. Full of fun one-liners and snappy jokes, Frequently Asked Questions About Time Travel is just innovative enough to justify its premise.
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Title |
Rotten Tomatoes Critic Score |
Rotten Tomatoes Audience Score |
|
Frequently Asked Questions About Time Travel (2009) |
35% |
61% |
2
Not Another Teen Movie (2001)
Directed by Joel Gallen
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Not Another Teen Movie
R
Comedy
Satire
8.3/10
Release Date
December 14, 2001
Runtime
89 Minutes
Cast
See All
-
Jaime Pressly
-
Mia Kirshner
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The star-studded teen comedy satire Not Another Teen Movie came out during a period when film pastiches were being made mainstream. Other sendups of typical genre fare, like Scary Movie, were growing in popularity, and Not Another Teen Movie pokes fun at the pitfalls of the classic teen rom-com. However, the film is memorable because of its highly raunchy subject matter and sense of humor and the over-the-top performances from the ensemble cast.
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Not Another Teen Movie: Every Easter Egg & Movie Reference Explained
Here’s a breakdown and explanation of every teen comedy film reference and Easter egg in the 2001 comedy parody movie Not Another Teen Movie.
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Iconic actors like Chris Evans, Chyler Leigh, and Jaime Pressly star as characters who embody the stereotypical archetypes that audiences have come to expect from the adolescent rom-com. Though it’s an interesting idea, and there are some witty, funny moments, Not Another Teen Movie goes from satirical to strange pretty quickly. In order to let the audience know how much of a joke the story is, Not Another Teen Movie hits you over the head with its references and takes some of the stories too far.
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Title |
Rotten Tomatoes Critic Score |
Rotten Tomatoes Audience Score |
|
Not Another Teen Movie (2001) |
32% |
55% |
1
The Cat In The Hat (2003)
Directed by Bo Welch
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The Cat in the Hat
PG
Adventure
Comedy
Release Date
November 21, 2003
Runtime
82 Minutes
Cast
See All
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Mike Myers
-
Alec Baldwin
-
Kelly Preston
-
Dakota Fanning
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The 2003 adaptation of Dr. Seuss’s beloved children’s book is a very loose take on the narrative. Off-putting and borderline terrifying at times, The Cat in the Hat stars Mike Myers as the titular cat, who brings magic and mischief to the lives of Conrad and Sally, the young children who serve as protagonists. Though the original book is a fantastical tale full of magical adventures, The Cat in the Hat is a darker, screwball version of the story.
Part of the reason The Cat in the Hat is so strange is its stylization and visual language, which border on surrealism, taking the viewer out of the narrative. The emotional core of The Cat in the Hat is about Conrad and Sally reconnecting with their absent mother, and it turns out the Cat’s hijinx is a method to bring the family together. Despite this touching message, The Cat in the Hat is a little too whacky to take seriously and too otherworldly to be pure comedy.
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Title |
Rotten Tomatoes Critic Score |
Rotten Tomatoes Audience Score |
|
The Cat in the Hat (2003) |
10% |
57% |
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Category: Entertainment