RANKED! Our 20 Favorite Comedy Movies of the Last 20 Years
Is there anything more rewarding than a good, guttural belly laugh? When was the last time you spewed water out of your nose due to a funny joke or ridiculous scenario in a movie? Classic comedies not only have the ability to get us through tough times in our lives but a great laugh fest can also set the tone for everyday life. The last 20 years have been the golden age of comedy, so we threw together a ranking of the films that hit our funny bones the hardest. Enjoy!
Cover Photo: Columbia Pictures
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20. 'I Heart Huckabees'
This movie didn't have a wide release but quickly became a cult classic. It's brilliantly acted and directed, and is so dry and sarcastic it'll make your tongue swell like you just ate 10 Warheads. It's one of the few comedies that asks existential and spiritual questions -- and Mark Wahlberg gets hit in the face with a giant rubber balloon. So. There's that.
19. 'O Brother, Where Art Thou?'
A Coen brothers classic, this fan favorite was loosely based on Homer's Odyssey, but with a quirky hidden treasure adventure twist that only the Coen brothers can pull off. Besides being quotable beyond its years, this film also dropped a hit folk/country song that still pops up at karaoke sessions, mostly in the Midwest.
18. 'The 40-Year-Old Virgin'
Judd Apatow introduced us all to two very important life lessons with The 40-Year-Old Virgin. First, don't be a 40-year-old virgin and, second, sell all your childhood toys on eBay immediately so you can start an adult business.
17. 'Bad Santa'
Is there anything better than Billy Bob Thornton as a drunken Santa Claus who secretly robs department stores during Christmas with the help of his elf-dressed, dwarf sidekick? The very first scene of the film gives a clear peek at what's in store, when Thornton (while dressed as Santa) pukes outside of a dive bar in the snow while his voice over proclaims, "I've seen some pretty shitty situations, but nothing has sucked ass more than this."
There's never been a film that has predicted the future of politics and the advancement of society more accurately than Idiocracy. The film was not only ahead of its time comedically, but was also, unfortunately, wildly close to what our current reality is.
15. 'High Fiedelity'
Back in the day when we all didn't just download music via streaming services, bitter and failing musicians posed as elitist music aficionados and flooded record stores daily to discuss what band currently sucked the most. High Fidelity hit the nail on the head with an unforgettable performance by Jack Black and a lead role that seemed to be written specifically for John Cusack.
14. 'In Bruges'
In this sleeper film, Colin Farrell plays a hit man who's struggling with the reality of what he does for a profession while also being on the outs with his current boss and "handler." He's been exiled to Bruges, Belgium, where he awaits his next assignment, it's driving him up the walls. There's also a midget party scene that includes a drug-induced conversation about the "inevitable race war."
No one knew the difference between merlot and any other red wine until this film explained how wine is actually made (and then they all hated merlot). Paul Giamatti plays a bitter, down-and-out writer with a serious wine problem fueled by an ex-wife problem and a best friend problem. Wine has never looked so good.
12. 'Team America: World Police'
When South Park's creators decided to make a movie about a secret government police squad dedicated to keeping order in the world, your interest was peaked. But, when you realized that they were making it with wooden marionettes, it was watched immediately. This flick pushed the limits of appropriate to the point of an initial NC-17 rating. They toned it down slightly in order give it a wide release, but it definitely didn't lose its edge in the process.
11. 'Borat: Cultural Learnings of America for Make Benefit Glorious Nation of Kazakhstan'
Sacha Baron Cohen crashed onto the comedy scene with reckless abandon on the wings of angels with Borat. He instantly had our attention and brought more humanity and excitement to the table than the No. 1 prostitute in all of Kazakhstan. We learned so much from his cultural explorations and societal investigations, we'll never be able to fully repay him for his massive contribution to our country.
"Classic" status is a term that gets thrown around too much, but Superbad was an instant classic worthy of the word. For most guys born in the '80s or early '90s, this movie pretty much summed up the teenage years with a perfect amount of disgusting, sexually confused comedy and high school B.S.
9. 'Step Brothers'
All you have to say is Adam McKay, Will Ferrell, and John C. Reilly. Houston, we've got a winner. These guys made us all want to move back home and get a bunk bed with our new stepbrother, then do karate in the garage.
8. 'Office Space'
Mike Judge (Beavis and Butthead, King of the Hill, Idiocracy) wrote and directed this perfectly executed explanation of adult life and the pitfalls of settling for a corporate job. It also made it seem OK to burn down your corporation's building and go work construction with the guy from The Drew Carey Show -- because, why not? You only live once, right?
7. 'American Pie'
Stifler time, baby! Seriously, is there anyone that hasn't quoted this movie at some point? Apple pie sales also went through the roof after its release. Who could've predicted that Jason Biggs' self-stimulation would also stimulate the agricultural economy in the process?
On paper, this Frank Oz film should've been a massive hit right away with Steve Martin, Eddie Murphy, Robert Downey Jr., but it only developed a cult following years after its release. This is the movie that proved Eddie Murphy could still make us laugh...and that movie producers are mostly scumbags.
5. 'Shaun of the Dead'
This movie introduced us all to Simon Pegg and Nick Frost as a dynamic British comedy duo. Shaun of the Dead was an absolutely brilliant reboot of the classic horror film Dawn of the Dead. It gave us an accurate comedic glimpse of what a zombie takeover would really be like for all the normal, underachieving blokes as they look up from their video games.
4. 'Wet Hot American Summer'
Wet Hot American Summer was essentially the jumping-off point for a ton of future comedy superstars. Marguerite Moreau, Paul Rudd, Christopher Meloni, Ken Marino, Joe Lo Truglio, Michael Ian Black, Amy Poehler, Bradley Cooper, Elizabeth Banks, Judah Friedlander and H. John Benjamin all appeared in this film. Several of them have Wet Hot American Summer to thank for their first real feature acting gig. Jewish summer camp has changed so many lives.
3. 'Tropic Thunder'
"I'm the dude playing the dude, disguised as another dude." This film should've won an Academy Award for overall brilliance. Every single scene is hilarious with a funny line-quotability percentage that ranks up there with classics like Ghostbusters, Animal House and Caddyshack. It also has quite possibly the most terrific (and barely recognizable) superstar cameo of all time.
Speaking of quotability, Anchorman gave us several all-time classic lines, including one that's all but renamed a major city in southern California: "Discovered by the Germans in 1904, they named it San Diego, which of course in German means: a whale's vagina."
1. 'Best in Show'
From the comedy geniuses that brought you This Is Spinal Tap comes the hilariously perfect mockumentary about a group of people we've all secretly wanted to know more about: professional dog show people. The cast is off-the-charts talented, and the mockumentary style makes you feel like you're a part of all the insanity that surrounds a national dog show...or more importantly, the insane people who show their dogs at these things. It's one of those movies that's so dry and tongue-in-cheek that if you don't get it right away, you may never really "get it."