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Underrated Comedy Movies of the 2000s, Ranked

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Underrated Comedy Movies of the 2000s, Ranked

The 2000s were a great decade for comedy. The decade is fondly remembered for the work of filmmaker and producer Judd Apatow and various comedic stars like Will Ferrell, Ben Stiller, Jack Black, Steve Carrell, and more. The Hangover, Knocked Up, Mean Girls, School of Rock, and Anchorman: The Legend of Ron Burgundy are just a few of the titles that have endured as modern comedy classics. While certainly, not every joke has aged incredibly well it is hard to deny the impact movies of the decade left on audiences.

Yet the decade was so rich for comedy films that plenty flew under the radar. While many of these did decent box office numbers and some generated Oscar buzz, they have sadly been overlooked over the years. Here are some of the most underrated comedies of the 2000s that are worth checking out.


8 Sideways

Searchlight Pictures

It may be challenging to say Sideways is underrated; after all, it was nominated for five Academy Awards including Best Picture and won Best Adapted Screenplay. However, it feels like the film has been eclipsed by other comedic Best Picture nominees of the decade like Little Miss Sunshine and Juno. Sideways might now be mostly remembered as a film that had a major impact on the wine industry, but that also overlooks just how funny the movie is and features great comedic performances by Paul Giamatti and Thomas Hayden Church.

7 In the Loop

Peter Capaldi, James Gandolfini in the movie In the Loop
Optimum Releasing

In the Loop is a feature film spin-off and continuation of the British series The Thick of It. It satirizes American politics at the time and particularly the politics surrounding the Iraq War. It is very much a movie of the moment, but an incredibly funny one, and it was even nominated for Best Adapted Screenplay at the Academy Awards.

Related: Best British Comedy Shows of All Time, Ranked

The movie is certainly worth checking out, particularly for Peter Capaldi reprising his role as Malcolm Tucker from The Thick of It and a great performance by the late great James Gandolfini. Any fan of Veep or Avenue 5 (both from the same writers) will adore this film.

6 Best in Show

Eugene Levy and Catherine O'Hara in Best In Show
Warner Bros.

Christopher Guest’s 2000 mockumentary Best in Show might be his most famous film, but it is still a criminally underrated comedy that does not get enough attention. The movie features performances by great comedic actors like Dan Levy and Catherine O’Hara as a married couple over a decade before they would play a couple on Schitt’s Creek.

It also features Parker Posey, Jennifer Coolidge, Jane Lynch, and the late great Fred Willard just to name a few, Best in Show is filled with great jokes and is a laugh-out-loud comedy worth watching.

5 Zack and Miri Make a Porno

Zack and Miri Make a Porno
The Weinstein Company

The 2000s were an interesting year for Kevin Smith, as he tried to transition out of his View Askewniverse. His two entries were the critically panned Jersey Girl and 2008’s Zack and Miri Make a Porno which is one of the filmmaker’s best works. Clearly inspired by the recent Judd Apatow comedies and bringing on Seth Rogen, Zack and Miri Make a Porno is both incredibly vulgar but emotionally sincere.

Related: Why 2008 May Be the Best Year For Comedy Movies

It tackles sex, love, and relationships in a way that is both juvenile and incredibly mature. While the film was a box office disappointment and might not be what anybody first thinks of when they imagine a Kevin Smith film, Zack and Miri Make a Porno is an underrated gem for both the filmmaker and the comedy genre in the decade.

4 Role Models

Role Models
Universal Pictures

Hard to imagine that Role Models was released just one week after Zack and Miri Make a Porno, but it was and despite being a decent hit and earning positive reviews Role Models has gone overlooked for quite a bit. Blending two comedic actors like Paul Rudd and Sean William Scott who were known for two different types of comedy films makes for a great pairing, but the story of two guys who don’t have their life together needing to be good influences on kids makes for a funny concept. Role Models features great lines, visual gags, and a hilarious over the top final LARP scene that has made it a cult classic and a fan favorite for years.

3 Down with Love

Renee Zellweger and Ewan McGregor Down With Love
20th Century Fox 

The exceptional Peyton Reed was one of the most notable comedy directors of the 2000s, and while most people remember The Break-Up or Yes Man, it is Down with Love that is his best film and also an underrated comedy. A throwback to the old-school 1960s rom-coms like Pillow Talk, Down with Love is a great recreation of the tone, style, and acting of those movies with stand-out performances by Ewan McGregor and Renée Zellweger. Down With Love is clever, subversive, and overall entertaining and makes one pine for the days when studios not only released comedies but took creative chances on them.

2 Burn After Reading

Brad Pitt dances in his gym uniform and headphones in Burn After Reading
Focus Features

Hot off their Academy Award win for No Country for Old Men, The Coen Brothers released Burn After Reading, which feels like the 2000s successor to their film The Big Lebowski. The very unique movie features an intricate plot with the main joke being that all the main characters are too self-absorbed, selfish, or dumb to truly grasp it. Actors like George Clooney, Francis McDormand, John Malkovich, Tilda Swinton, and Brad Pitt get to show off their comedic muscles in a comedy with no moral or lesson and is just one giant screw-up building on top of itself.

1 Kiss Kiss Bang Bang

Downey Jr. and Kilmer in Kiss Kiss Bang Bang
Warner Bros.

Shane Black’s 2005 Kiss Kiss Bang Bang might not have been a box office hit but it is without a doubt one of the funniest movies of the decade. It features a sharp script with richly defined characters, that is both a throwback to the 1980s buddy cop films that Black refined with Lethal Weapon while also updating it for the 21st century. The movie is both one of the most underrated Christmas movies and the most underrated comedies of the decade.

Kiss Kiss Bang Bang might be one of the most important comedies of all time, as it was one of the most high-profile return projects for Robert Downey Jr. which helped him land the role of Iron Man in the MCU. Shane Black even did uncredited rewrites for Iron Man, helping establish the film’s comedic tone which would lay the groundwork for the entire MCU, and Black himself would direct Iron Man 3. All of this can be traced back to Kiss Kiss Bang Bang.

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