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The Funniest Movies Of The 2000s

Updated October 5, 2020 98.4k votes 6.8k voters 238.6k views120 items

List RulesVote up the comedies released between January 2000 and December 2009 that make you laugh the hardest.

Here is a list of the funniest movies of the 2000s. These are the greatest comedy films released in the 2000-2009 range of hilarity, some of which are the best comedies of all time. Judd Apatow and Steve Carell struck comedy gold in the early 2000s with The 40-Year-Old Virgin, as he continued, he forgot Sarah Marshall and knocked up Katherine Heigl. The top comedies of the 2000s came in the form of the ultra absurd; take a look at the montage scenes in Wet Hot American Summer as an example. 

Other possibilities for the funniest movies from the 2000s were indie packages, as was the case with Little Miss Sunshine. O Brother, Where Art Thou? and Eight Crazy Nights made millions laugh their butts off, as did comedy films like Elf and Meet The Parents. This list compiles those comedies that landed on the silver screens and changed the landscape for funny movies - some of which were overlooked at the time but have since gained dedicated audiences. Or, they made the list because they were just plain hilarious.

Be sure to vote up your favorites so other comedy fans know what to watch next and vote down the ones they should avoid.

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  • 26
    Role Models
    591
    324

    Role Models

    Elizabeth Banks, Louis C.K.

    Released2008

    Directed byDavid Wain

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  • 27
    Miss Congeniality
    739
    559

    Miss Congeniality

    Sandra Bullock, William Shatner

    Released2000

    Directed byDonald Petrie

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  • 28
    American Pie 2
    510
    356

    American Pie 2

    Alyson Hannigan, Tara Reid

    Released2001

    Directed byJames B. Rogers

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  • 29
    School of Rock
    924
    732

    School of Rock

    Sarah Silverman, Jack Black

    Released2003

    Directed byRichard Linklater

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  • 30
    Scary Movie
    757
    550

    Scary Movie

    Carmen Electra, Anna Faris

    Released2000

    Directed byKeenen Ivory Wayans

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  • 31
    Hot Fuzz
    746
    533

    Hot Fuzz

    Cate Blanchett, Martin Freeman

    Released2007

    Directed byEdgar Wright

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  • 32
    Knocked Up
    839
    603

    Knocked Up

    Jessica Alba, Eva Mendes

    Released2007

    Directed byJudd Apatow

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  • 33
    Shrek 2
    787
    623

    Shrek 2

    Cameron Diaz, Eddie Murphy

    Released2004

    Directed byKelly Asbury, Andrew Adamson, Conrad Vernon

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  • 34
    Road Trip
    544
    431

    Road Trip

    Amy Smart, Andy Dick

    Released2000

    Directed byTodd Phillips

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  • 35
    Austin Powers: Goldmember
    681
    493

    Austin Powers: Goldmember

    Britney Spears, Beyoncé Knowles

    Released2002

    Directed byJay Roach

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  • 36
    Grandma's Boy
    567
    422

    Grandma's Boy

    Jonah Hill, David Spade

    Released2006

    Directed byNicholaus Goossen

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  • 37
    O Brother, Where Art Thou?
    643
    521

    O Brother, Where Art Thou?

    George Clooney, John Goodman

    Released2000

    Directed byEthan Coen, Joel Coen

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  • 38
    Me, Myself & Irene
    532
    362

    Me, Myself & Irene

    Jim Carrey, Anna Kournikova

    Released2000

    Directed byPeter Farrelly, Bobby Farrelly

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  • 39
    Bad Santa
    513
    413

    Bad Santa

    Lauren Graham, Billy Bob Thornton

    Released2003

    Directed byTerry Zwigoff

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  • 40
    Borat: Cultural Learnings of America for Make Benefit Glorious Nation of Kazakhstan

    Released2006

    Directed byLarry Charles

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  • 41
    Waiting...
    500
    408

    Waiting...

    Ryan Reynolds, Emmanuelle Chriqui

    Released2005

    Directed byRob McKittrick

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  • 42
    Ocean's Eleven
    416
    373

    Ocean's Eleven

    Brad Pitt, Julia Roberts

    Released2001

    Directed bySteven Soderbergh

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  • 43
    Ice Age
    529
    404

    Ice Age

    Jack Black, Ray Romano

    Released2002

    Directed byChris Wedge, Carlos Saldanha

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  • 44
    Harold & Kumar Go to White Castle
    78
    32

    Released2004

    Directed byDanny Leiner

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  • 45
    White Chicks
    587
    504

    White Chicks

    Shawn Wayans, Marlon Wayans

    Released2004

    Directed byKeenen Ivory Wayans

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  • 46
    National Lampoon's Van Wilder
    357
    333

    National Lampoon's Van Wilder

    Ryan Reynolds, Tara Reid

    Released2002

    Directed byWalt Becker

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  • 47
    The Princess Diaries
    359
    332

    The Princess Diaries

    Anne Hathaway, Mandy Moore

    Released2001

    Directed byGarry Marshall

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  • 48
    Hitch
    405
    406

    Hitch

    Will Smith, Eva Mendes

    Released2005

    Directed byAndy Tennant

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  • 49
    Jay and Silent Bob Strike Back
    439
    349

    Jay and Silent Bob Strike Back

    Ben Affleck, Matt Damon

    Released2001

    Directed byKevin Smith

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  • 50
    I Love You, Man
    485
    376

    I Love You, Man

    Rashida Jones, Paul Rudd

    Released2009

    Directed byJohn Hamburg

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