25. Team America: World Police (2004)
Our first film comes to us via the creative duo responsible for South Park in Trey Parker and Matt Stone. Team America is a wild ride — there’s no other way to put it. As one can see from the promotional poster, the film utilized a form of puppets over actual people. Be honest — you’ve seen that gif over and over of a ‘puppet’ projectile vomiting. Well, that happened to come from this movie. There are some things which wouldn’t be appropriate today when it comes to film. With that said, we applaud Parker and Stone for taking a risk in making a major motion picture with puppetry.
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24. Get Him to the Greek (2010)
Get ready for your Russell Brand fix. The eclectic and esoteric comedian-turned-actor was quite popular during the beginning of the 2010’s. Get Him to the Greek enabled Brand to portray a druggie rock star dealing with the reality of his career’s mortality. As Jonah Hill’s record label attempts to make Brand famous again (culminating in a major show), Hill has to safely get him from London to Los Angeles. Of course, things aren’t that easy — and Brand’s character Aldous Snow takes Hill for a wild ride. A quick shoutout must also go to Rose Byrne for playing Brand’s raunchy ex-girlfriend. She gave a terrific performance as Jackie Q.
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23. Forgetting Sarah Marshall (2008)
Aldous Snow appears again in this film as the main antagonist to Jason Segel’s character. In order to get over a rough breakup, Segel leaves LA and heads to Hawaii. As fate would have it, he runs into his ex-girlfriend (Kristen Bell) and her new beau (Brand). Awkward hangouts ensue between the group, and Segel’s spirits are raised by meeting a local (Mila Kunis). Of course, Bell’s character gets jealous. The lurid scenery in this movie is fantastic, and the Jonah Hill cameo is absolutely legendary. We even get a look at Segel’s character performing a vampire-themed rock opera.
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22. Austin Powers in Goldmember (2002)
The third movie of the Austin Powers trilogy, Goldmember ushered in two heavyweights in Beyonce and Michael Caine. Though most sequels are honestly a waste of time, this one was actually funny! It offered a fresh take on the storyline, which involved Dr. Evil and Austin coming to the realization that they’re actually brothers. In the process, Caine’s suave persona worked terrifically as Austin’s dad, and Beyonce played the role as the main female protagonist brilliantly. Some of the jokes may be a bit outdated/geared towards the time when the film came out. Regardless, it’s a very good addition to the franchise as a whole.
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21. Scary Movie (2000)
Scary Movie was first of multiple films within the franchise. As the opening one, it set the tone for others as a parody of many horror films that came before it. The Wayans Brothers would utilize a number of different techniques when depicting things from the past. In a sense, it was paying homage to those classic films. Additionally, this film set the scene for some insane yet comedic moments. It’s difficult to quantify the exact plot of this story. You’d just be better off watching it if you’ve yet to see the film.
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20. Road Trip (2004)
Now, here’s the run on ‘trip’ movies. To kick it off, Road Trip features four guys who — shockingly — go on a road trip. The motive involves sneakily obtaining a tape which was accidentally sent to one of the guy’s girlfriends. Seann William Scott was at the height of his American Pie popularity here. He carried this film in parts, as did Breckin Meyer. Director Todd Phillips (Old School, The Hangover) showcased his usual trademarks from a comedy standpoint. There were some really funny moments…and also some gross ones in the process.
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19. EuroTrip (2004)
EuroTrip often gets lost in the shuffle when it comes to comedies over the last 25 years. It’s most likely due to the fact it wasn’t an Apatow/Rogen/Goldberg production. Nonetheless, there’s some real funny moments in this movie — including a shocking cameo from Matt Damon dressed as a punk singer. Essentially, the main protagonist heads to Europe over the summer (along with his friends) to pursue a love interest.
Along the way, you’re given many of the typical ‘European stereotypes’ — in addition to some unexpected surprises. Aside from Damon, we saw terrific cameos from Fred Armisen, Lucy Lawless, Jeffrey Tambor, Diedrich Bader, and Vinnie Jones. The movie was directed by Jeff Schaffer, and written by Schaffer, Alec Berg and David Mandel. You may previously know these guys from their extensive work on Seinfeld and Curb Your Enthusiasm (among other projects).
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18. Knocked Up (2008)
As the title would suggest, a one-night stand between Seth Rogen and Katherine Heigl resulted in an unexpected pregnancy. Rogen — a notorious slacker — was forced to get his ‘stuff’ together. Meanwhile, Heigl struggled with the fact that she was not only hiding the pregnancy from her workaholic job, but that she might not have wanted to be having Rogen’s baby. In the end, the audience is given the happy ending it wants.
Along the way, a cast of characters — namely Rogen’s on-screen/real-life friends — provide much of the humor. In classic Judd Apatow fashion, we’re of course talking about stalwarts Jonah Hill, Jay Baruchel, wife Leslie Mann, Paul Rudd, Martin Starr, Bill Hader, Ken Jeong, his daughters Iris and Maude, and Kristen Wiig.
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17. Bridesmaids (2011)
Bridesmaids was a nice change from the usual comedy hits. Often times, female actors garner roles in comedies which don’t enable them to really showcase their comedic chops. In this case, the story is totally female-forward, with virtually the entire cast (sans Chris Dowd) being leading ladies. Virtually all of the performances from the main group involve those ‘going for it’. We’re talking about Kristen Wiig’s scene in the airplane, Melissa McCarthy’s scene in the bathroom, and the back-and-forth between Wendi McLendon-Covey and Ellie Kemper. The cameos from Rebel Wilson, John Hamm, and the band Wilson Phillips added even more punch to the story.
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16. Pineapple Express (2008)
‘Stoner’ movies are usually hit or miss. Some can be wildly funny, while others will fall flat on their proverbial face without much in the way of direction or creativity. During this era, there was not a more prolific comedy group than the faction of Evan Goldberg, Seth Rogen, and Judd Apatow. The aforementioned braintrust came up with this wacky story — where Rogen and James Franco get caught up in a hectic ordeal when being chased by drug dealers and gangs galore. The supporting cast is really where this movie shines. Unsurprisingly, Apatow was able to get the likes of Ken Jeong, Craig Robinson, Rosie Perez, Bill Hader, Kevin Corrigan, Amber Heard, Gary Cole, Bobby Lee, Troy Gentile, and Danny McBride to participate.
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15. Elf (2003)
Elf rightfully can be categorized as a Christmas film. But, at the same time, it’s also a comedy — and a film which appeals to all people during the holiday season. Seeing a grown man run around New York City in tights is funny in and of itself. When you factor in the reality that the man is Will Ferrell, it’s taken to a new level. There’s a real sense of sweetness in this film. It’s not the most captivating — nor is it going to win a ton of major awards. All the same, the humor extracted from this movie is quite good (as is the overall pacing).
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14. Super Troopers (2001)
For whatever reason, there’s something funny about bumbling cops who can’t seem to do their job right. Yet, you still find yourself rooting for them as endearing characters. The comedy team Broken Lizard expertly crafted this cult classic — both in terms of writing the project as well as acting in it. You’ve essentially got a ragtag team of state troopers up in New England trying to do their job to the best of their abilities. After failing to adequately fulfil their responsibilities, the group decides to make up for it in the way of nabbing some notorious drug dealers.
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13. Meet The Parents (2000)
This is a wholesome comedy for the entire family, and one which does a delicately apt job at appealing to virtually all age demographics watching it. We’ve seen this before…the boyfriend meeting the family — with the hopes of impressing them. All of a sudden, the boyfriend (Stiller) is thrown into a situation where he’s dealing with the father (Robert De Niro) who’s more than a handful. This film touches on many issues that families face. Duly, it’s got just the right amount of slapstick humor to make it all worthwhile. Plus, we even love the cameo by Owen Wilson as the jealous ex-boyfriend-turned-carpenter-turned-wedding officiant.
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12. Tropic Thunder (2008)
This film had a terrific cast (as evidenced by the picture above). Virtually all of the A-Listers shown above (Robert Downey Jr., Tom Cruise, Jack Black, Ben Stiller, Bill Hader) have experience as dramatic actors. However, this plot enabled them to ‘play’ in this parody of a war movie. There are some aspects of this film which didn’t age gracefully. However, it was fascinating to see both Downey Jr. and Cruise step back from their usual serious roles and attempt something quite different from their usual path (especially Cruise).
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11. Borat (2006)
This movie was a total phenomenon. We’ve seen various comedians dress up as other characters in a movie (such as Eddie Murphy). However, British actor Sacha Baron Cohen flipped the script a bit — as he portrayed a fake character out in the real world with people not ‘in’ on the joke. The raw reactions of these people when meeting Borat makes it that much more funny.
Essentially, this character billed from Kazakhstan makes his way to the United States — where his aim is to essentially document real-life in the United States. Of course, you see every stereotype you can imagine in this, along with poking fun at various sections of the country. There are some cringe-worthy parts, but for the most part Cohen really gives it a go.
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10. Step Brothers (2008)
Step Brothers shouldn’t work on its surface. Two 40-somethings act like 10-year-olds when their divorcee parents end up marrying/moving in together. Seeing John C. Reilly and Will Ferrell sharing bunk beds, chopping pumpkins with a Randy Jackson-signed samurai sword, and wearing Chewbacca masks seems truly absurd. It is — but in the best way possible. This isn’t a movie for everyone. It takes a certain sense of humor to appreciate the script. However, the performances of our two leading men were great. Richard Jenkins was terrific as the dad/stepdad, and brother Derek (Adam Scott) was cast perfectly as the antagonist who simply wanted to gain acceptance from his brother.
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9. Zombieland (2009)
This film followed a few before it as a comedic look at zombies. After breaking out in Superbad, Emma Stone led this cast — which also features Abigail Breslin and Jesse Eisenberg. Of course, Woody Harrelson functions as the veteran force of the group. Essentially, these four are aiming to seek safety amidst a zombie outbreak. Along the way, a ton of heart is exposed. The four main characters are ultimately seeking companionship amidst the treacherous environment. Plus, the Bill Murray cameo is golden.
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8. Shaun of the Dead (2004)
This film indirectly helped to usher in the ‘zombie’ craze which became very trendy in pop culture, film, television, and other mediums. British comedians Nick Frost and Simon Pegg lead this romp — which shows a group of people (comedically) aiming to ward off a zombie invasion spreading throughout London. While there is some gore and violence, it’s done in a very comedic way. This wasn’t meant to be a big-budget film. However, it’s become a cult classic — and top-10 comedy from the past 20ish years. Adding to the quality is the fact Edgar Wright directed this film rather early in his career.
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7. Zoolander (2001)
Despite debuting more than 20 years ago, Zoolander still holds up terrifically well. It’s one of those films which is so dumb at points, that it simply works. It’s a parody of the fashion industry — particularly those who are models. We see Zoolander (Ben Stiller) get involved with a maniac of a fashion designer (Will Ferrell) aiming to assassinate the Prime Minister of Malaysia over the cost of producing clothing. Utterly ridiculous, it’s also fantastically funny. The celebrity cameos add even more hilarity to the film. Chief among them, Billy Zane and David Duchovny.
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6. The 40-Year-Old Virgin (2005)
The title really says it all. Along with The Office, this film single-handedly launched Steve Carell into the category of comedic heavyweights. Our titular character plays a middle-aged man fixated more on collectable toys and video games rather than the pursuing of a relationship. Galvanized by a group of work pals (which includes Seth Rogan), Carell’s character Andy sets out to date. He meets the woman of his dreams (Catherine Keener). However, he must reveal his ‘situation’ before things get too serious with the woman he grows to fall in love with.
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5. Wedding Crashers (2005)
It’s wedding season! Owen Wilson and Vince Vaughn star as two lifelong bachelors who have no intention of falling in love seriously…yet get roped into a wacky weekend by two sisters from the same family. The actual ‘code’ attributed to crashing weddings (stage 5 clinger!) is something that people in real life have attempted to imitate. Rachel McAdams plays off Wilson’s character immensely well, and this platform enabled Vaughn to really star as a comedy lead. We also got to meet Bradley Cooper before he became…Bradley Cooper. No one will forget the impromptu football game featuring the aforementioned trio, an energetic Christopher Walken, and a sprawling green lawn.
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4. Anchorman: The Legend of Ron Burgundy (2004)
Will Ferrell is a giant within the genre of comedy. You can point to upwards of 10-15 films in which he’s been the leading man. However, Anchorman might be his ultimate opus. You can see the joy on Ferrell’s face when riffing with his co-stars. The improv level within this film is at an extremely high level. It helps in keeping the flow organic — which in turn allows the film to really hit its stride. No one thinks of Christina Applegate as a beacon for laughs. Yet, she’s the perfect foil to Ferrell and his endearing ridiculousness.
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3. Old School (2003)
Another Todd Phillips hit, Old School in many respects set the scene for many comedies to follow. It was clearly influenced by some of the comedy hits from the ’70’s and ’80’s (especially Animal House). With the frat house as the backdrop, we saw these group of men beset by ‘Peter Pan’ syndrome create this environment which bred friendship, a brotherhood, and ultimate silliness. Luke Wilson isn’t the funniest guy around, but his laid-back persona actually worked well with the bigger personalities of Will Ferrell and Vince Vaughn. Jeremy Piven was terrific as the antagonist school dean. Duly, we can’t forget some of the more iconic scenes (the ‘pledge’ scene off the building, the final physical contest montage, anything involving Blue).
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2. The Hangover (2009)
This movie took the world by storm. Director Todd Phillips took a somewhat simple premise (a bachelor party weekend) and flipped it on its head with raunchy hijinks, mass hysteria, and a host of noteworthy supporting characters. The main crew (Ed Helms, Bradley Cooper) was enhanced with the ultimate breakout of Zach Galifianakis. His role as Alan became universally known — to the point where people still dress up like him for Halloween. We’d be remiss if we didn’t mention Ken Jeong’s portrayal of an effeminate gangster.
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1. Superbad (2007)
Superbad remains a masterclass in comedic brilliance. This film appeals to multiple generations — whether you grew up as a ’90’s kid or lived through earlier decades. The soundtrack is brilliant, and the dichotomy of Jonah Hill’s anxious nature coupled with Michael Cera’s passive attitude really works. This marked the emergence of Christopher Mintz-Plasse (as the famed McLovin). Duly, the duo of Seth Rogen and Bill Hader CRUSHED it as the bumbling yet hilarious cops.
This is as quotable a film over the last 20 years as there is — regardless of genre. While we have strong elements of comedy throughout, there’s also layers of friendship, wholesomeness, and self-actualization at its core. Superbad will forever remain as a giant within the realm of comedy.
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