The Most Underrated Comedies Of The 2000s

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Vote up the comedies that deserve a bigger audience.

With the September 11 attacks, the Iraq War, and the Global Financial Crisis all taking place in the 2000s, audiences were in desperate need of some escapist entertainment. There were many highly successful and well-remembered films during the 2000s, but these are the most underrated comedies of the decade. They may have gotten lost amidst more popular releases, or they may have found some success only to be forgotten with time. Either way, these comedies deserve to be revisited and/or reconsidered.

A sense of humor can be personal and vary from person to person, as comedy itself is highly subjective. What one person finds funny may be a mere annoyance to another. Some of these underrated comedies are silly and sophomoric in nature, embracing the more immature instincts of the genre. Others are more intelligent and rely on razor-sharp wit. Then there are the dark comedies that embrace the comic possibilities of controversial subject matter. Whether the humor comes from the physicality of slapstick, the cleverness of dialogue, or mere shock value, these comedies deliver the laughs.

  • 1
    1,290 VOTES

    Down with Love is a tongue-in-cheek comedy set in the 1960s, following womanizer and successful writer Catcher Block (Ewan McGregor) in his romantic efforts to win over aspiring author Barbara Novak (Renée Zellweger), who has written a self-help book encouraging women to replace sex with chocolate. Down with Love is a parody of the sanitized romantic films released amid the self-censorship of the 1960 film industry, primarily referencing the films of Doris Day and Rock Hudson.

    The double entendres within these films is exaggerated to comedic levels here, making the sexual references more explicit while retaining the wholesome facade on the surface. Unfortunately, it's likely that a large percentage of modern audiences were unfamiliar with the films being parodied, and Down with Love performed lower than expected.

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  • 2
    2,210 VOTES

    Directed by Mike Judge, Idiocracy is a satire that follows US Army librarian Joe Bauers (Luke Wilson) after he undergoes a hibernation experiment and wakes up in a dumbed-down dystopian future society where he is the smartest man alive. The country is run by President Dwayne Elizondo Mountain Dew Herbert Camacho (Terry Crews), who handles the responsibility with the seriousness of a reality TV host.

    When it was released in 2006, Idiocracy seemed like an extreme reaction to the direction of society, though many have pointed out the similarities in society since Donald Trump’s presidency and the emergence of “fake news” as a common outcry from those unwilling to accept facts. In some ways, Idiocracy was so prescient in its prediction of the future that it feels like a warning as well as a comedy.

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  • 3
    1,633 VOTES

    Alex (Allen Covert) is a 35-year-old video game tester going nowhere in his life, forced to move in with his grandmother (Doris Roberts) and her two friends (Shirley Knight and Shirley Jones) after being evicted. The living situation ends up being for the best, giving Alex the motivation to work on his own video game and the confidence to begin a relationship with his new boss (Linda Cardellini).

    The concept of a stoner comedy involving a grandmother was clever enough for Grandma’s Boy to stand out amidst multiple 2000s comedies centered on male protagonists in arrested development. While not nearly as successful as the Judd Apatow films or others from Adam Sandler’s Happy Madison production company, Grandma’s Boy has just as many laughs.

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  • Though the plot has the structure of a hard-boiled detective narrative, Kiss Kiss Bang Bang prioritizes humor above all else. When small-time New York crook Harry Lockhart (Robert Downey Jr.) accidentally stumbles into a movie audition while running from the police, he earns a trip to Los Angeles for a screen test. While on a ride-along with private investigator "Gay" Perry van Shrike (Val Kilmer) for research, Harry gets entangled in a murder investigation that involves his childhood crush (Michelle Monaghan).

    Loosely based on the 1941 Brett Halliday novel, Bodies Are Where You Find Them, Kiss Kiss Bang Bang is a meta take on the detective genre, filled with comedically self-referential jokes. The edginess of Downey Jr.’s role took on extra significance given the fact that the star had begun the decade with legal issues that resulted in temporary incarceration. While Kiss Kiss Bang Bang played a part in reviving his career, it is safe to assume the film would have been even more successful after the actor’s involvement in the highly popular Marvel Cinematic Universe. In that light, this film has the added bonus of a hilarious scene with the future Iron Man kissing a past Batman.

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  • IRS agent Harold Crick (Will Ferrell) lives a life of routine and efficiency - until he wakes up one morning hearing the voice of a narrator describing everything he does. The voice belongs to famed author Karen Eiffel (Emma Thompson), who is known for writing books in which the protagonist tragically dies. Harold is desperate to change this ending, having recently fallen in love with a local baker (Maggie Gyllenhaal).

    Stranger than Fiction provides Ferrell the opportunity to play against type, in a role that is somewhat similar to Jim Carrey’s more dramatic turn in The Truman Show; the two share some narrative similarities, as well. Ferrell may play the absurd situation straight, but there is plenty of humor found in it, as well, including scenes in which the panicked IRS agent seeks out advice from a literature expert (played by Dustin Hoffman) to try and figure out what type of story he is in.

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  • 6
    1,030 VOTES

    Death to Smoochy is a dark comedy unexpectedly set within the world of the children’s entertainment industry. When an FBI sting exposes the misconduct of children’s program host "Rainbow" Randolph Smiley (Robin Williams), the disgraced celebrity sets out to sabotage his wholesome replacement (Edward Norton). Death to Smoochy was a massive box-office failure, despite its clever and dark premise that was clearly referencing the lucrative accomplishments of Barney & Friends in the 1990s.

    Directed by Danny DeVito, who also has a supporting role as a corrupt agent, Death to Smoochy has gained a cult following over time. Williams is shockingly funny playing against type as the antihero, while Norton’s casting as the good-natured children’s program host couldn’t be more spot-on.

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