The 21 Best Comedies of the 2000s, Ranked

• Written by: Jaime Kennedy, Nick Swardson, Fax Bahr, Adam Small
• Directed by: John Whitesell
• Starring: Jamie Kennedy, Taye Diggs, Regina Hall, Anthony Anderson
• Watch it if you like: Half Baked and Grandma's Boy

If you didn't laugh your a$$ off to Malibu's Most Wanted, we're not sure if we can rock with you. Where do we start? The pimp walk they were doing in the beginning? B-Rad crashing his father's campaign announcement to hop out the back of Escalade to for an impromptu (and unasked for) performance? B-Rad acting like he robbed the convenience store? There's so many hilarious moments in this film, and who can ever forget "traffic, traffic, looking for my chapstick, feeling kind of carsick, there's a Ford Maverick?" One of the greatest raps of all time.

• Written by: David Rohn, Jay Scherick
• Directed by: Dennis Dugan
• Starring: Martin Lawrence, Steve Zahn
• Watch it if you like: Bad Boys and Blue Streak

Another underrated comedy of the 2000s, National Security is admittedly a movie that probably wouldn't fly in 2023 considering some of the jokes and the overall synopsis of the film. That said, the film is Martin Lawrence quite possibly at his peak funniest, and it all starts at the beginning when he's training (and inevitably gets kicked out) of the police academy for a ridiculous set of events that you'll have to watch the movie to understand. Steve Zahn was the perfect counterpart to Martin's foolery, and together they made a great cop duo. What da problem is?

• Written by: Steve Koren, Mark O'Keefe
• Directed by: Frank Coraci
• Starring: Adam Sandler, Kate Beckinsale, Christopher Walken
• Watch it if you like: The Hot Chick and Yes Man

Remember 2006's Click starring Adam Sandler and Kate Beckinsale? If not, now is the time to refresh your memory. Sandler stars as Michael Newman, a career man that's seemingly preoccupied with work and not enough on his marriage. Newman meets a rather eccentric inventor portrayed by Christopher Walken, who gives him a time control remote. How does Newman choose to use this remote and what happens afterwards? You'll have to watch the movie for that.

• Written by: Tyler Perry
• Directed by: Darren Grant
• Starring: Tyler Perry, Kimberly Elise, Cicely Tyson, Shemar Moore
• Watch it if you like: Why Did I Get Married?

For many of us who around in the 2000s, Diary of a Mad Black Woman was our first introduction to the legend that now is Tyler Perry. What makes the film so great is that isn't just a comedy as there are elements of drama and serious themes and topics throughout. The moments that are funny, however, are funny, and the one-liners Madea threw out still remain classics that are referenced in popular culture today.

• Written by: Simon Pegg, Edgar Wright
• Directed by: Darren Grant
• Starring: Simon Pegg, Nick Frost, Timothy Dalton, and Jim Broadbent
• Watch it if you like: Knives Out and Moon

Starring Simon Pegg, Nick Frost, Timothy Dalton, and Jim Broadbent, 2007's Hot Fuzz is about two cops that are investigating a series of murders in West Country, and that's about as serious as it gets as the film is full of bumbling, stumbling, and witty puns. In our opinion, one of the funniest moments of the film is when Nicholas Angel (Simon Pegg) is in the convenience store, turns around to face a stand of DVDs, looks the DVD cover of Keanu Reeves in Point Blank, turns back around to the cashier and determines that he needs "to finish the job." Why? Keanu Reeves? We don't know, but it's hilarious.

• Written by: Mark Brown, Don D. Scott, Marshall Todd
• Directed by: Tim Story
• Starring: Cedric the Entertainer, Ice Cube, Anthony Anderson, Michael Ealy
• Watch it if you like: Friday and Beauty Shop

People forget how funny Barbershop was. This movie was funny. Centering in on Calvin (Ice Cube), a young barber who inherits his deceased father's barbershop. Tasked with overseeing the shop, at first Calvin finds the job a bit pointless, but as time passes, he begins to connect more with the very interesting set of characters (shoutout to Eddie), and realizes that maybe it's not so bad after all. A classic.

• Written by: Rawson Marshall Thurber
• Directed by: Rawson Marshall Thurber
• Starring: Vince Vaughn, Ben Stiller
• Watch it if you like: Anchorman: The Legend of Ron Burgundy

Here's the deal with Dodgeball. Peter La Fleur (Vince Vaughn) owns a struggling gym called Average Joe's Gym that runs into even more issues when a much fancier gym, Globo-Gym ran by White Goodman (Ben Stiller), opens up. Since Average Joe's was already on the outs, naturally the opening of Globo-Gym hurts its prospects even more, and the gym is on the verge of going out of business unless Peter is able to raise $50k to pay his mortgage. The solution? For Peter and the Average Joe's Gym gang to enter a dodgeball competition for cash.

The problem? White Goodman takes his Globo-Gym crew and enters the competition as well. Fun stuff.

• Written by: Robert Ramsey, Matthew Stone
• Directed by: Malcolm D. Lee
• Starring: Bernie Mac, Samuel L. Jackson
• Watch it if you like: Head of State

We had to get a Bernie Mac entry on here because our guy was one of the funniest in the 2000s (of all time as well), and we decided to rock with Soul Men. Bernie Mac and Samuel L. Jackson is a combination we would have loved to see more of, and it's just one more reason why Mac's untimely death in 2008 still remains so sad. Mac, however, left a great body of work, and Soul Men is an example of that. If you want to see two funny nutcases playing off each other, improvised lines, and hilarious moments, then you gotta watch this film.

• Written by: Steve Faber, Bob Fisher
• Directed by: David Dobkin
• Starring: Vince Vaughn, Owen Wilson
• Watch it if you like: The 40-Year-Old Virgin

Where would the 2000s have been without Wedding Crashers? One of 2005's best films, Wedding Crashers starred Vince Vaughn and Owen Wilson as two divorce mediators who make great use of their free time by crashing weddings. We won't spoil for those that haven't seen the film yet, but just know we wish we could have us much as these two divorce mediators. They are simply living the life.

• Written by: Steve Carell, Jude Apatow
• Directed by: Jude Apatow
• Starring: Steve Carrell, Paul Rudd, and Katherine Keener
• Watch it if you like: Role Models and Pineapple Express

Honestly, we're not sure how The 40-Year-Old Virgin would be perceived in present day as some might find the film to be a case of age and sexuality shaming. All we can attest to is the fact that in 2005 it was considered to be one of the movies of the decade. If you can take it for what it is (a movie), and appreciate the performances of Steve Carell and Paul Rudd, you'll definitely be able to get some laughter in.

• Written by: Ben Stiller, Justin Theroux, Etan Cohen
• Directed by: Ben Stiller
• Starring: Ben Stiller, Robert Downey Jr., Tom Cruise, Jack Black
• Watch it if you like: Dolemite Is My Name

We've said it before and we'll say it again. Tropic Thunder is one of the funniest movies to come out of the 2000s. The idea of dropping four actors (who were actually actors in real life) in the middle of the real jungle in the effort to liven up their performances for a movie they were shooting was genius, and they picked some of the best actors in the game to take on those parts. We don't really get films like Tropic Thunder anymore, and that's a shame.

• Written by: Jason Segel, Nicholas Stoller
• Directed by: Nicholas Stoller
• Starring: Jason Segel, Kristen Bell
• Watch it if you like: Along Came Polly and Knocked Up

Who can forget about Forgetting Sarah Marshall? Another gem from 2008, Nicolas Stoller and Jude Apatow were the masterminds behind this ultra-hilarious comedy starring Jason Segel and Kristen Bell as struggling musician and tv star couple. The two wind up breaking up, and both end up in the same hotel after the breakup which results in nothing but pure 2000s comedy. It's a cult-classic for a reason.

• Written by: Jeff Nathanson
• Directed by: Brett Ratner
• Starring: Chris Tucker, Jackie Chan
• Watch it if you like: Rush Hour

Alright, we know Rush Hour 2 technically falls under the action category, but dammit, Chris Tucker made this a comedy as well! If Rush Hour 2 doesn't have you doubling over with laughter we're not sure what to tell you other than you're seriously missing out. Forever a legendary movie from the early 2000s.

• Written by: Jared Hess, Jerusha Hess
• Directed by: Jared Hess
• Starring: Jon Heder, Efran Ramirez
• Watch it if you like: Bill & Ted's Excellent Adventure

The best way to describe Napoleon Dynamite is that it had/has all of the elements to technically qualify as a bad film. The movie is slow-paced, doesn't seem to have much of a plot/story, has a main character with a very one-dimensional personality, and yet...it came together beautifully. That formula is only one that could have worked with these particular director, writers, and actors involved, and it really hasn't been successfully done since. Some have tried, but it hasn't quite become as iconic as Napoleon Dynamite.

• Written by: Steve Koren, Mark O'Keefe, Steve Oedekerk
• Directed by: Tom Shadyac
• Starring: Jim Carrey, Morgan Freeman, Steve Carrell, Jennifer Aniston
• Watch it if you like: Liar Liar

Anytime Jim Carrey is involved in something you already know you're going to be laughing your butt off. In short, things aren't going too hot for TV reporter Bruce Nolan (Carrey). Frustrated, he challenges God to do a better job controlling the events of life. God, who is portrayed by Morgan Freeman, let's Bruce take the reigns, and well...you'll have to watch the movie to get the answer as to whether or not it works out for Bruce.

• Written by: Wright and Simon Pegg
• Directed by: Edgar Wright
• Starring: Simon Pegg, Kate Ashfield, Nick Frost, Lucy Davis.
• Watch it if you like: Funny People and The Proposal

Some people saw the magic in Shaun of the Dead, while others did not. Hopefully everyone is able to see the magic now as it's about a man in his 30s who's deemed a loser (Pegg), who works at an electronics store and lives with his best friend. Unbelievably, Shaun has managed to get a girlfriend (who's just about at the end of her rope with him), who is constantly left frustrated because he won't grow up. Does Shaun grow up? All we'll say is that he gets forced out of his element when zombies invade the town.

• Written by: Court Crandall, Todd Philips, Scott Armstrong
• Directed by: Todd Philips
• Starring: Luke Wilson, Will Ferrell, Vince Vaughn
• Watch it if you like: Eurotrip

Old School is all over the place, but in a good way. The film stars Luke Wilson as an attorney named Mitch, who finds out that his girlfriend engaging in group sex. This devastates him, and he decides to start fresh as a bachelor. Mitch moves near a college campus, gathers his two best buddies, and the apartment becomes a place for the wild and the wild only.

• Written by: Will Ferrell, Adam McKay
• Directed by: Adam McKay
• Starring: Will Ferrell, John C. Riley
• Watch it if you like: Wedding Crashers and Forgetting Sarah Marshall

What do you get when two lazy aimless middle-aged losers who still live at home are forced into becoming roommates when their parents marry? Step Brothers is what you get. Can you believe some people didn't like this movie when it came out? Oh well. The important thing is that most people did and still do.

• Written by: Jon Lucas, Scott Moore
• Directed by: Todd Phillips
• Starring: Bradley Cooper, Ed Helms, Zach Galifianakis, Justin Bartha
• Watch it if you like: Superbad and Get Hard

Nearly fifteen years after its release, The Hangover remains the ultimate bachelor party gone wrong. Who would have ever known this movie would have the impact that it did? The Hangover still gets referenced in popular culture, still goes viral on social media, and still manages to add on fans with each passing year. Like we said, the ultimate bachelor party gone wrong that still hasn't been. topped.

• Written by: Seth Rogan, Evan Goldberg, Greg Mottola
• Directed by: Greg Mottola
• Starring: Jonah Hill, Michael Cera
• Watch it if you like: American Pie, Good Boys

One word here. McLovin. If you are 1990s baby/2000s kid, then Superbad was a game changer for you. With the movie coming out during the final stretch of summer break, everybody came back to school talking about. Everybody. If you weren't around to experience in first-hand, then watching it on streaming is the next best thing. Memes and clips don't do this film justice. Watch it.

• Written by: Xavier Cook, Andy McElfresh, Michael Anthony Snowden, Keenan Ivory Wayans, Marlon Wayans, Shawn Wayan
• Directed by: Keenan Ivory Wayans
• Starring: Keenan Ivory Wayans, Shawn Wayans
• Watch it if you like: Big Momma's House

We're rocking with White Chicks as our number one. It was absolutely hilarious at the time of its release, is still absolutely hilarious, and continues to have cultural relevance and significance in popular culture. The only question we have left is when the sequel is coming.