35 Best Hidden Gem 2000s Comedy Movies

Comedies can sometimes struggle to find an audience. Recently, the genre has been pretty hit or miss, meaning even the best comedies struggle at the box office, although they seem to be doing much better on streaming. However, comedies are far from what they were during the early years of the new millennium when hits like Anchorman: The Legend of Ron Burgundy and Bruce Almighty dominated the box office and became certified classics.

There’s no denying that the 2000s were a great time for the genre, producing some incredible and widely-known comedies that are now considered modern triumphs. The genre’s success also led to some underrated ones that deserve a lot more love from modern audiences. Indeed, not every film was a winner right off the bat, and some comedies from the noughties were unfairly overlooked during their original theatrical run. Luckily, thanks to streaming, modern audiences can rediscover these underrated 2000s comedy movies and finally give them their dues.

35

‘The Girls Next Door’ (2004)

Directed by Luke Greenfield

Emile Hirsch jumped into noughties stardom with the 2004 coming-of-age sex comedy The Girl Next Door. The film centers on Matthew, a Georgetown-bound senior struggling to come up with the tuition money. His life changes when he meets his new neighbor, Danielle (Elisha Cuthbert), who he soon discovers is a former adult star.

Much more innocent and subtle than something like American Pie yet far more daring than the traditional PG-13 teen comedy, The Girl Next Door is an unexpectedly sweet comedy that never forgets the awkwardness of adolescence. Hirsch and Cuthbert share an incredible dynamic, effortlessly selling a less-than-believable story via sheer and enviable chemistry, the kind most movies would kill to have. A scene-stealing Timothy Olyphant, very obviously having the time of his life, further enhances the film as the main and truly detestable antagonist.

34

‘Saved!’ (2004)

Directed by Brian Dannelly

Mandy Moore, Jena Malone, Patrick Fugit, and Macaulay Culkin star in the 2004 teen satirical comedy Saved! The plot of the modern teen movie follows Mary, a young girl who agrees to lose her virginity to her ex-boyfriend, hoping to “cure” his being gay. She then becomes pregnant, leading her to be ostracized by her devoutly Christian classmates.

Saved! is wickedly funny and surprisingly insightful. The stellar cast elevates a sometimes tepid screenplay afraid of taking its wild premise all the way. Malone is particularly compelling as the besmirched Mary, while Mandy Moore is excellent as her sanctimonious and overbearing nemesis. The film might not reinvent the teen comedy genre, but it remains an entertaining and biting effort.

Saved!

Release Date

June 11, 2004

Runtime

92 minutes

33

‘Charlie Bartlett’ (2007)

Directed by Jon Poll

The late Anton Yelchin stars in the 2007 coming-of-age comedy Charlie Bartlett. The plot follows the titular character, an unpopular teenager who begins giving therapeutic advice and prescription drugs to his new classmates to further his social status. Hilarious antics and consequences follow this decision, as he runs into unexpected challenges during their “sessions.”

Robert Downey Jr. is Yelchin’s nemesis in Charlie Bartlett, creating a witty and thorny look at teen angst and social struggles. The film is uneven and afraid to turn its engaging premise into something truly radical. However, Yelchin’s performance single-handedly elevates it, turning it into one of the best comedies of the 2000s.

32

‘Frequently Asked Questions About Time Travel’ (2009)

Directed by Gareth Carrivick

Following in the same vein of friendship-comedy turned high-stakes chaos as Edgar Wright‘s Cornetto trilogy, Frequently Asked Questions About Time Travel takes the classic structure to the world of time travel science fiction. The film follows a trio of best friends who are on what seems like just another ordinary day at the pub, yet quickly transforms into a dangerous mission when a series of time leaks begins affecting their time at the pub. The trio soon find themselves jumping across time to find a solution, hoping not to get completely lost in the process.

Much like the best films that inspired it, the greatest aspects of Frequently Asked Questions About Time Travel and its comedy come less from the inherent insanity of its premise and plot developments and more from the genuine chemistry and bond between its lead characters. Ray, Pete, and Toby all work off of each other perfectly, filling in the holes in each other’s personalities and truly feeling like a genuine group of real-life best friends. Their friendship elevates the entire film, complete with its wild twists and comedic antics. – Robert Lee

31

‘Adventureland’ (2009)

Directed by Greg Mottola

Jesse Eisenberg and Kristen Stewart star in the 2009 comedy Adventureland. Set in the summer of 1987, the plot centers on a recent college grad who takes a job at a run-down amusement park, where he meets a wealthy but troubled college student with whom he develops a romantic relationship.

Adventureland has a stellar supporting cast, including Ryan Reynolds, Kristen Wiig, Martin Starr, and Bill Hader. The film thrives on its nostalgic feel, effortlessly capturing the breezy and distinctive quality of classic 80s comedies. Eisenberg’s hectic energy finds the right partner in Stewart’s well-known subdued approach, resulting in a compelling and quirky pairing that makes Adventureland a delightful watch.

30

‘Cromartie High School: The Movie’ (2005)

Directed by Yudai Yamaguchi

While many live-action adaptations of anime series fail to live up to the animated antics and energy of their source material, Cromartie High School: The Movie perfectly encapsulates the comedic madness of the original series. The surrealist comedy film acts as a satire of a classic slice of life high school anime, seeing its quirky characters attempting to navigate the most chaotic and vicious high school imaginable. However, the students at the school prove to be even more unpredictable and zany than the school itself, with two of the students even being a gorilla and a feisty robot.

Rarely has a live-action adaptation been so similar in tone and style to its source material, perfectly translating the zany and absurdist comedy of the series to a live-action film format. The film is filled with a wide array of hilarious, non-stop gags, to a point where at least one is going to land with the audience in some way. Its prospects as a live-action adaptation of an already relatively obscure anime have made it an extremely obscure comedy, but one that is certainly worth seeking out for any fans of Japanese culture or comedy. —Robert Lee

29

‘Fido’ (2006)

Directed by Andrew Currie

The Canadian hidden gem Fido is an underrated but great zombie comedy. Set in a world where humans have domesticated zombies, the plot follows Timmy, a young boy who forms a close and meaningful bond with his family’s zombie, Fido. However, things go awry when Fido’s collar malfunctions, sending him on a murderous rampage.

Fido works largely thanks to Sir Billy Connolly‘s unhinged performance in the titular role. The film expertly balances genuine emotion with humor and everything expected from a zombie movie—mainly gore, blood, and shock. Fido is one of the best comedies of the 2000s, a hidden gem worthy of a modern reappraisal.

Fido

Release Date

September 7, 2006

Runtime

92 minutes

28

‘Watching the Detectives’ (2007)

Directed by Paul Soter

Seeing Cillian Murphy in the rare comedic role, Watching the Detectives sees him as Neil, a lonely film geek and owner of the local video store, content to live his life of solitude through his favorite films. His life view suddenly changes, however, when he meets Violet (Lucy Liu), a strange yet captivating woman who is far from ordinary and always seems to be getting up to chaotic schemes and playing pranks on Neil. While hesitant at first, it quickly becomes apparent that by spending more and more time with Violet, Neil’s life is finding itself becoming just as unpredictable as Violet’s.

While this style of glamorized romantic comedy plot that plagued the 2000s has largely seen itself result in countless films that have aged like milk, Watching the Detectives is the rare exception that has aged like a fine wine. The connection and relationship that blossoms between Neil and Violet come from a genuine place of intrigue and connection, despite all the antics and comedy that surrounds them. The film also has a simple yet effective message of going outside of one’s comfort zone, creating a signature experience that acts as a truly underrated gem among 2000s romantic comedies. – Robert Lee

27

‘In the Loop’ (2009)

Directed by Armando Iannucci

Armando Iannucci‘s 2009 satirical black comedy In the Loop is among the best comedies of the 2000s. The plot centers on the profane and intense political spin doctor Malcolm Tucker, who travels to the US to fix his Prime Minister’s mistake before war erupts between two countries.

Like most of Iannucci’s work, In the Loop is a profane and scathing critique of real-world politics. The film aims for the invasion of Iraq, delivering a thought-provoking yet still hysterical and unhinged film that will keep audiences in stitches. In the Loop is one of the funniest comedies from the 2000s, a clever but insightful depiction of the absurdity and intricacies of Anglo-American relationships.

In The Loop

Release Date

January 22, 2009

Runtime

106 minutes

26

‘Wristcutters: A Love Story’ (2007)

Directed by Goran Dukić

Dark comedy is always a relatively tricky balancing act, with only the truly great comedy films able to find levity, laughter, and a compelling message out of a situation and material that is obscenely dark in nature. Wristcutters: A Love Story, is one such dark yet sickly comedic experience, following a depressed man who decides to end his life after breaking up with his girlfriend, only to find himself in an aimless, run-down afterlife. However, after soon realizing that his ex-girlfriend has also ended her life, he sets out on a road trip in order to find her.

Wristcutters is highly creative when it comes to the mundane and monotonous depiction of the afterlife, compounding its overall lessons and themes about not taking things for granted and the importance of life itself. However, just because the afterlife itself is a barren wasteland doesn’t mean that its supporting cast is without entertainment, as the likes of Shea Whigham, Leslie Bibb, and a wild villain performance from Will Arnett transform the film into a comedic goldmine. —Robert Lee