Top 20+ Funniest Movies of All Time to Make You LOL | Cheezburger

• 01

  Pineapple Express, 2008

  
  via imdb

  Director: David Gordon Green
  Writers: Judd Apatow, Seth Rogen, Evan Goldberg
  Runtime: 117 minutes

  Box Office: $102.4 million

  Rotten Tomatoes: 68%

  Judd Apatow's production company very nearly raised a decade of comedy-lovers. And 2008's Pineapple Express may be one of its most-beloved efforts. The quirky and talented supporting cast, the cleverly convoluted antics, and the overwhelming presence of its main stars (marijuana, Seth Rogen, and James Franco) made this romp a classic for stoners and humor-hunters alike. 

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• 02

  Blazing Saddles, 1974

  
  via Amazon

  Director: Mel Brooks

  Writers: Mel Brooks, Norman Steinberg, Andrew Bergman, Richard Pryor

  Runtime: 93 minutes

  Box Office: 119 million

  Rotten Tomatoes: 88%

  
  What can we say? Mel Brooks' Blazing Saddles is a must for comedy-lovers of all ages. Zoomers may not be drawn to the nearly 50 year old movie, but once the self-aware jokes start hitting, the film is close to ageless. This sly and satirical spin on classic Westerns pits corrupt politician Hedley Lemar (Nod to Hedy Lamarr?) against a black sheriff (Cleavon Little) he appointed in the hopes of orchestrating a town's downfall. Needless to say, things don't go as planned - and the ensuing antics are a riot. 

• 03

  Bridesmaids, 2011

  
  via imdb

  Director: Paul Feig 
  Writers: Annie Mumolo, Kristen Wiig
  Runtime: 125 minutes

  Box Office: $288 million

  Rotten Tomatoes: 90%

  2011's Academy and Golden Globe-nominated Bridesmaids ushered in a new era for women in comedy by giving Apatow's crew of man-children a run for their money. Kristen Wiig, Maya Rudolph and the rest of the gang play women who are not afraid to be disgusting, drunk, and sometimes even obnoxiously selfish. The contrast between comedic restraint, raw emotional character arcs, and all-out potty humor made this female-led project feel completely fresh - and it all holds up today. 

• 04

  Zoolander, 2001

  
  via imdb

  Director: Ben Stiller

  Writers: Writers: Ben Stiller, John Hamburg, Drake Sather

  Runtime: 89 minutes

  Box Office: 60.8 million

  Rotten Tomatoes: 64%
   

  Modeling has always seemed like a ridiculous gig to us regular people, but Ben Stiller took the profession's absurdity to the next level with this movie about a dimwitted male supermodel Derek Zoolander. As the model agonizes over a rivalry with a younger model (Hans, masterfully played by Owen Wilson), he becomes embroiled in a dangerous conspiracy at the hands of evil fashion designer Jacobim Mugatu (Will Ferrell). Between the all-star cast (David Bowie makes an appearance), their goofy performances, and the ridiculous jokes, Zoolander hits all the marks.

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• 05

  The Room, 2003

  
  via imdb

  Director: Tommy Wiseau

  Writer: Tommy Wiseau

  Runtime: 99 minutes

  Box Office: 4.9 million

  Rotten Tomatoes: 23%

  
  There are a lot of movies out there that fall into the category of "so bad it's good." But none of them compare to the insane hilarity of The Room. Written and directed by the enigmatic Tommy Wiseau, this drama has reached cult classic status with its wooden acting, laughably bad production, and its melodramatic - and sometimes confusing - plot. Never have we ever seen a love triangle with so little chemistry. That said, if we're giving points for enthusiasm, The Room easily gets extra credit; Wiseau's passion for his magnum opus oozes out of every hilariously awkward scene. 

• 06

  The Princess Bride, 1987

  
  via MGM Studios

  Director: Rob Reiner

  Writer: William Goldman 

  Runtime: 98 minutes

  Box Office: 30.9 million

  Rotten Tomatoes: 98%

  
  There's a reason Rob Reiner's take on William Goldman's The Princess Bride has a whopping 98% fresh on Rotten Tomatoes. For one, the part-parody, part-family adventure is a hit with viewers of all ages. As Chicago Tribune critic Dave Kehr aptly put it, the film is "a pastiche of fairy tales and half- forgotten movies," a trait that makes the story and aesthetic instantly familiar for all generations. Then there's the sarcasm and self-aware humor, which is judiciously applied by narrator Peter Falk, playing a grandfather reading a fairy tale to his grandson (Fred Savage). While the plotlines of romance, a kidnapped princess, action and revenge aren't anything new, it's the attitude that sets The Princess Bride apart. The insanely talented cast (Cary Elwes, Robin Wright, Mandy Patinkin) doesn't hurt either. 

• 07

  Wedding Crashers, 2005

  
  via IMDB

  Director: David Dobkin

  Writers: Steve Faber, Bob Fisher

  Runtime: 119 minutes

  Box Office: $288 million

  Rotten Tomatoes: 76%

  The dynamic duo of Owen Wilson and Vince Vaughn play a pair of reprehensible womanizers who crash weddings to get lucky with no strings attached. When Wilson's character, John Beckwith, falls for a politician's daughter their well-oiled seduction machine starts to malfunction - much to Jeremy's (Vaughn) chagrin. While a tad predictable, the star-studded cast (Rachel McAdams, Isla Fisher, Christopher Walken), adult themes, and roasting of WASPy families made Wedding Crashers one of the decade's instant classics. 

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• 08

  Meet the Parents, 2000

  
  via imdb

  Director: Jay Roach

  Writers: Greg Glienna, Mary Ruth Clarke, Jim Herzfeld 

  Runtime: 108 minutes

  Box Office: $330.4 million

  Rotten Tomatoes: 84%

  
  While Zoolander may be Ben Stiller's magnum opus, it was romantic comedies like Meet the Parents and There's Something About Mary that really jump-started the actor's career. This movie pits Stiller's male nurse, Greg Focker, against his intimidating future father-in-law - a suspicious retired CIA agent masterfully played by Robert De Niro. The series of unfortunate events surrounding their introduction were funny (and gross) enough to warrant not one, but two sequels. 

• 09

  Dumb and Dumber, 1994

  
  via imdb

  Directors: Peter Farrelly, Bobby Farrelly 

  Writers: Peter Farrelly, Bobby Farrelly, Bennett Yellin 

  Runtime: 107 minutes

  Box Office: $247 million

  Rotten Tomatoes: 68%

  
  The aggressive stupidity of Dumb and Dumber may not be for everyone, but it's certainly a 20th century comedy classic. Jim Carrey and Jeff Daniels live up to the name of this Farrelly brothers comedy, marrying their dimwitted ways with slapstick humor. Their many mistakes lead them on a cross-country trip that's mostly spent toying with kidnappers. It really lives up to the ancient "it's about the journey, not the destination" adage. 

• 10

  Superbad, 2007

  
  via Sony Pictures

  Director: Greg Mottola 
  Writers: Seth Rogen, Evan Goldberg 
  Runtime: 113 minutes
  Box Office: $121.5 million
  Rotten Tomatoes: 88%

  At the risk of seeming like we have a boner for Seth Rogen, here's another one from our favorite pothead turned ceramics expert. The film follows a pair of friends (Jonah Hill, Michael Cera) on a quest to have an epic night of underage partying. While the movie is extremely vulgar in both language and subject-matter, this take on a coming-of-age film still manages to be a heartwarming tribute to teen friendship. 
   

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• 11

  Top Secret!, 1984

  
  via Amazon

  Directors: David Zucker, Jim Abrahams, Jerry Zucker

  Writers: David Zucker, Jim Abrahams, Jerry Zucker, Martyn Burke

  Runtime: 90 minutes

  Box Office: $20.5 million

  Rotten Tomatoes: 75%

  The parody masters behind Airplane! are responsible for Val Kilmer's debut in this action comedy that spoofs everything from WWII spy films (namely Casablanca) to Elvis Presley's goofy 1950's musicals. Kilmer plays Nick Rivers, an American rock and roll star who finds himself stuck in West Germany helping the resistance rescue a scientist from the merciless fascist government. Despite the semi-serious subject matter, nearly every scene is jam-packed with groan-worthy jokes, making it perfect for regular viewings - especially when under the influence of laugh-inducing substances. The film's familiar faces (Omar Sharif, Peter Cushing, Jim Carter) are a nice bonus. 

• 12

  Knocked Up, 2007

  
  via Amazon

  Director: Judd Apatow

  Writer: Judd Apatow

  Runtime: 133 minutes

  Box Office: $357 million

  Rotten Tomatoes: 89% 

  
  While some may argue that The 40 Year Old Virgin made way for the rest of Apatow Productions' features, we think it's Knocked Up that really sparked the mania. And judging by its impressive Rotten Tomatoes rating and box office pull, people seem to agree. In this comedy, an accidental pregnancy bring journalist Alison Scott (Katherine Heigl) and slacker Ben Stone (Seth Rogen) together for a messy journey navigating pregnancy, parenthood, and compatibility. Despite its serious themes, the film keeps things pretty lighthearted thanks to its killer supporting cast (Leslie Mann, Paul Rudd, Jonah Hill).

• 13

  Wet Hot American Summer, 2001

  
  via IMDB

  Director: David Wain

  Writers: Michael Showalter, David Wain

  Runtime: 97 minutes

  Box Office: $295.2 thousand

  Rotten Tomatoes: 38%

  Don't let the low box office gains or Tomatometer score fool you. This movie was ahead of its time where humor is concerned. The incredibly horny movie follows a group of camp counselors trying to get laid and/or get high. The hormonally-charged satire features a pretty insane cast: Paul Rudd, Bradley Cooper, Amy Poehler, Elizabeth Banks, and Christopher Meloni all make appearances. With talent like that, it should be on everyone's watchlist. 

  
   

  
   

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• 14

  Forgetting Sarah Marshall, 2008

  
  via Amazon

  Director: Nicholas Stoller

  Writer: Jason Segel

  Runtime: 111 minutes

  Box Office: 105.8 million

  Rotten Tomatoes: 83%

  When composer Peter Bretter (Jason Segel) is unceremoniously dumped (in the nude!) by his TV star girlfriend, Sarah Marshall (Kristen Bell), he decides to take a trip to Hawaii in an attempt to get over their flawed 5 year relationship. Unfortunately, Sarah is staying at the same resort with her new boyfriend, British rock star Aldous Snow (Russell Brand). It's a huge letdown for Peter, but the hotel concierge, Rachel (Mila Kunis), hooks him up with a lavish suite to dull some of the pain. The suite does less to lift his spirits than Rachel herself, something that doesn't go unnoticed by an unsatisfied Sarah. Jealousy and jokes ensue. Best of all? This comedy isn't afraid to get emotional, which definitely makes it one of our favorite Apatow Productions features. 

  
   

• 15

  Rush Hour, 1998

  
  via Rotten Tomatoes

  Director: Brett Ratner

  Writers: Ross LaManna (story), Jim Kouf (screenplay)

  Runtime: 98 minutes

  Box Office: $244 million

  Rotten tomatoes: 61%

  
  We'll be the first to admit that this movie hasn't aged very well. But if you can get past the stereotypes, and Chris Tucker's ties to Jeffrey Epstein, you're in for a very enjoyable action-packed comedy. The chemistry between Jackie Chan and Tucker is incredible, and the movie is filled with timeless moments (that War! scene) that really never get old. The thrilling kidnapping plot doesn't hurt either. 

• 16

  What We Do in the Shadows

  
  via Amazon

  Directors: Jemaine Clement, Taika Waititi

  Writers: Jemaine Clement, Taika Waititi

  Runtime: 86 minutes

  Box Office: 7.2 million

  Rotten Tomatoes: 96%

  What We Do in the Shadows is more than a vampire movie. The mockumentary comes from the brilliant minds (and acting talent) of Flight of the Conchords' Jemaine Clement, and Thor: Ragnarok's Taika Waititi. So, obviously, it's wildly hilarious. More than that, it's a very fresh take on the genre. Of course there's brooding and bloodsucking, but the brooding is as theatrical as a heartbroken teenager going through their first goth phase. And the bloodsucking, well, it's pretty goofy. The "insight" we get on vampires is priceless: they're neurotic, insecure, and experience agonizing breakups and obsessions. The flick definitely evokes a sort of Christopher Guest charm, but really goes for it with the goofiness, making it accessible to people who prefer their humor to be a bit more literal. It's a fun-filled ride, and best of all? The film was adapted for American television by FX - so there are three seasons of vampiric antics to be enjoyed if What We Do in the Shadows tickles your fancy.

  
   

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• 17

  American Pie, 1999

  
  via imdb

  Director: Paul Weitz

  Writers: Adam Herz

  Runtime: 95 minutes

  Box Office: 101.7 million

  Rotten Tomatoes: 61%

  
  Tweens and teens reveled in the raunchy and humiliating humor of American Pie in 1999, making lines like "One time at band camp" the era's equivalent of  "That's what she said." The movie follows a group of friends on a quest to lose their virginities. The high schoolers (with the exception of Stifler) make a pact to do the deed before high school graduation, engaging in some seriously embarrassing behaviors in the process. The movie is helped by its ensemble cast, featuring Jason Biggs, Seann William Scott, Natasha Lyonne, Mena Suvari, and Jennifer Coolidge, as the one and only 'Stifler's Mom.' The horny teen movie may not be for everyone, but there's a reason the original gang got back together for three sequels. 

• 18

  Shaun of the Dead, 2004

  
  via imdb

  Director: Edgar Wright

  Writers: Simon Pegg, Edgar Wright

  Runtime: 99 minutes

  Box Office: $30 million

  Rotten Tomatoes: 92%

  
  Nothing shakes up a dull and thankless existence quite like a zombie apocalypse. In this gruesomely funny film ( the first installment of Edgar Wright's Three Flavours Cornetto trilogy) Simon Pegg plays the titular character, a bored, miserable electronics salesman coping with a breakup. Until, of course, the undead start popping up about town. Wright's romp pays comedic homage to the zombie films of George Romero - who was actually so impressed with the movie that he asked the writers for cameos in 2005's Land of the Dead. 

• 19

  Step Brothers, 2008

  
  via IMBD

  Director: Adam McKay
  Writers: Will Ferrell, Adam McKay
  Runtime: 95 minutes
  Box Office: 121.8 million
  Rotten Tomatoes: 55%

  Step Brothers is an absolute revelation for people who like immature and obnoxious humor. Will Ferrell and John C. Reilly play a pair of manchildren who live with their mother and father, respectively. When their parents get married and decide to blend their families, the pair of 40 year olds have nothing but contempt for one another. Eventually, against all odds, they develop a friendship. Unfortunately the camaraderie isn't enough to end their childish antics, which lead to their newlywed mother and father to go their separate ways - forcing the two to work together to mend their family. While the movie is largely comprised of stupidity and gross-out humor, it will definitely appeal to fans of Ferrell and McKay's signature style of silly. 

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• 20

  Borat, 2006

  
  via imdb

  Director: Larry Charles

  Writers: Sascha Baron Cohen, Peter Baynham, Anthony Hines

  Runtime: 84 minutes

  Box Office: $262.6 million

  Rotten Tomatoes: 91%

  The antics of Sascha Baron Cohen's Borat are both riotously funny and completely cringey. But that's kind of the point. The titular character is tasked by the Kazakh government to make a documentary about American culture. While the blaringly ignorant and offensive humor from Borat take center stage, the film is actually a bracingly clever satire, and a scathing commentary of American society.

  
   

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