The Playbook For The Modern Man

These Are The Most Iconic Comedy Films Of All Time

Dark, witty and absolutely inappropriate jokes make the world go round.

Dark, witty and absolutely inappropriate jokes make the world go round. Whether you’re in the office or hanging out, an intuitive quip is essential for every man’s survival. Why not draw influence from the best comedy films around? From old-school slapstick or blunt deadpan humour, check out our list of top flicks for a healthy laugh and necessary comedic relief when you need it most.  

Trading Places

Trading places is a farce commentary on the 80’s “Decade of Greed”. When two millionaires (Duke & Duke) bet they can breed conman bum Billy Ray Valentine (Eddie Murphy) into a magnificent bastard, snobby managing director Louis Winthrope III (Dan Ackroyd) gets the short end of the stick. Turning his life upside down as Murphy takes over his job, house and network of friends. As the Duke’s plan begin to unravel, the two men and their cohorts devise to take down the brothers. Dark, cruel but utterly hilarious, Trading Places is a must see on every man’s watchlist.   


Happy Gilmore

Ludicrous, over-the-top, and ridiculously funny, Happy Gilmore is the prime example of a 90’s Adam Sandler flick. The story revolves around aggro hockey player, Happy (ironically enough), who can whack a golf ball further than the pros. When his beloved grandmother hits financial issues, Happy tests his luck on the PGA tour. His main rival – Shooter McGavin, a pro who sees Happy as a disgrace to the game of golf. Happy’s loud, rambunctious and will certainly have golfers changing the way they play the game.

Dazed & Confused

Your last day of high school was probably nothing like Randall “Pink” Floyd’s (Jack London)back in Texas 1976. Cruisin’ around in a 1970 Chevy Chevelle SS 454, endlessly smoking grass and causing neighbourhood ruckus. If you’ve pondered on what life was like in America during the 70’s, here’s your free chanc eto time travel. From soundtrack to wardrobe and the retro verbiage – Dazed & Confused is everything quintessential. Where Matthew McConaughey coined the film’s catchphrase “That’s what I love about these high school girls, man. I get older, they stay the same age.”

Anchorman: The Legend of Ron Burgundy

Anchorman doesn’t pull strength of it’s storyline, no. Ron Burgundy and his notoriously funny news team are known for their ridiculous antics and random comical situations. Burgundy, a shallow and pretentious news anchor, is baffled when a woman is added to the news room for “diversity”. From there the stage is set for digs at male-dominated media, love interests and news network competition. The film doesn’t try to be smart or witty, but rather revels in it’s stupidity as Will Ferrell leads the way.

Hot Fuzz

For those who thought Simon Pegg couldn’t top his Shaun of the Dead performance, guess again. When London cop Nicholas Angel (Pegg) is relocated to a quaint English village, his foolish new partner and him uncover a menacing conspiracy. Although the plot is mediocre, the comedic expertise lies in the films catchy dialogue, fast jokes and enjoyable action scenes. Director Edgar Wright does tongue-in-cheek cop-comedy with a twist of creativity for Hot Fuzz- definitely one to see for continuous adrenaline rushes and healthy laughs.



When an airplane crew takes ill, only one person is able to land the plane – an ex-fighter pilot who’s afraid to fly. A situation which normally precedes impending doom, is met with complete satire in this classic spoof film. Brush up on your 80’s pop culture prior to watching. The films deadpan in-humour and jokes reference back to the era and can fly overhead…easily.

The Hangover

A bunch of guys hit up Vegas for their buddies bachelor party – in the morning no one remembers anything. Watch as these guys go through farce hell to find their missing friend before his wedding while trying to hold off his questioning finance. Bradley Cooper, Zach Galifianakis and Ed Helms, with the assistance of Mike Tyson & Mr. Chow (Ken Jeong) make for a solid flick and heed the warning “What happens in Vegas, stays in Vegas”.

American Pie

Relive your virgin high school days alongside these four teens who set out on the sexual conquest to lose “it” by prom night. And before you think it’s another kitchy high school film, stop there. American Pie goes further than the stereotypical teenage life. Each character has their own distinct story which adds a level of depth to them you don’t find in similar films. One liners, gags and outlandish situations bring endless hilarity to a original, and entirely relatable, storyline done well by American Pie.

Austin Powers: International Man of Mystery

Michael Myers puts forth the first James Bond parody film with a stereotypical 60’s twist. Riddled with crude sexual innuendo, awfully corny jokes and poor British dental work, Austin Powers is by far one of the funniest “arch nemesis takes over the world” action-comedy films to date.

Old School

Mitch’s (Luke Wilson) life comes to a halt when he comes back from a business trip to find his wife amongst a menacing threesome. In an attempt to revitalise their newly single mate, his best lads led by Beanie (Vince Vaughn), decide to relive their college years by starting a fraternity. Totally cliche, seriously cheap laughs and wild parties with girls wrestling in KY jelly bring your reckless college nostalgia back to life in this big studio comedy.


There’s Something About Mary

We’ve all had that one dream girl. She was stunning, charismatic and ultimately, wouldn’t bat a look until she found out you were wealthy. Ben Stiller led this sophomoric comedy as he was presented the opportunity to rekindle with the long sought-after, Mary. The Farrley Brothers did comedy right with it’s blunt digs on every race, demographic, gender and orientation. It’s unfortunately relatable, highly amusing and will certainly keep you laughing until close.


Friday’s easily one of those charismatic films you can watch a few times a year. Not only is it easy to laugh with, the film offers a lighter look on southern LA culture which contrasts prior films like Boyz N The Hood. The plot revolves around two friends, Smokey (Chris Tucker) and Craig (Ice Cube) who smoke their dealers weed and struggle to find a way to pay him back. It’s the film that made the mark for Chris Tucker and continues to be one of the funniest movies around today.

Step Brothers

Brennan Huff (Will Ferrell) and Dale Doback (John C. Reilly) have everything in common – from sleepwalking to being unemployed and devoid of any of life’s responsibilities. The two 40 year old men are essentially overgrown children. When their parents force them to live together, their personalities collide whilst hilarity ensues. It’s a typical Ferrell film, so be prepared for the absurd, “stupid” comedy that leaves us coming back for more Will Ferrell year by year.  

Forgetting Sarah Marshall

First off, Kristen Bell, who plays Sarah Marshall, is seriously beautiful. And any guy that loses her would hate to know she’s now mackin’ a famous rockstar. Imagine being bloody ex-boyfriend Peter (Jason Segel) when he runs into the lovebirds in Hawaii. Through a series of awkward interactions watch as crude humour, understated jokes and well-timed digs create a memorable vacation for everyone. Leaving you guessing if Segel will fall for Sarah one last time, or hook it with the alluring, way cooler Mila Kunis.

The Royal Tenenbaums

Wes Anderson brings us the dysfunctional Tenebaum family. A quirky group of oddball child prodigies who reunite when their father, Royal, declares he’s dying. The story is incredibly emotive and aided by the enchanted Wes Anderson cinematography we know and love. Owen Wilson, Bill Murray, Ben Stiller and others comprise a charming cast in this eclectic dark, tragi-comedy.


Blazing Saddles

Dedicated fandom will call Blazing Saddles “the funniest film of all time”, which in part is true for it’s arguably Mel Brooks best work. The story revolves around a corrupt politician played by Gene Wilder who’s determined to ruin his white western town. In doing so, he hires a black sheriff, for in it’s time (the 70’s) was considerably shocking. Enjoy traditional slapstick scripts, copious sight gags and overtly sexual perversion which brings Blazing Saddles forth as one of the best comedies of it’s time.

Crocodile Dundee

Crocodile Dundee is another time-after-time film for those days you’re in need of a good laugh. A classic “fish out of water” flick, American reporter Linda Kozlowski investigates legendary Aussie “Crocodile Dundee” and brings him back to NYC. He’s charismatic, humourous and carries an eccentric spirit of adventure through the streets of the Big Apple. The well-known trope has been redefined – Never bring an Aussie to a knife fight.

Dumb & Dumber

You’ll either love or hate the “stupid-funny” comedy performance put forth by Jim Carrey and Jeff Daniels in this cult classic. Every line delivered reflects how… well, dumb these two guys are. As they travel across the United States to return a forgotten suitcase to Carrey’s limo passenger, they find themselves amongst a kidnapping scheme and a mess of trouble. The dialogue is plagued with slapstick joke after joke and certainly shaves a few points off your IQ post viewing.

Knocked Up

Ben Stone (Seth Rogan) ends up living every man’s nightmare –  when a one-night stand leads to a baby. And where Knocked Up separates itself from the typical teenybopper dram-com is it’s well-written script and, yes, heartfelt scenes. A comedic spin on how adults act when unexpected pregnancy arises. The female lead Alison Scott (Katherine Heigl) is just as lively as her counterpart producing a clever flick with grinning snickers and engaging side plots.

Wedding Crashers

Personally, Wedding Crashers is one of my favourite comedy films from the 2000’s and redefined the way men see rom-com’s. Vince Vaughn and Owen Wilson play two divorce mediators who spend their weekends picking up girls at random weddings. Their relationship showcases an ideal for best mates who intuitively get each other and party hard. Delivering a performance streamlined with inappropriate jokes, witty digs and memorable times… until someone falls for the wrong girl.


Kingsman: The Secret Service

Fans of Bond and old-school action films with take to Kingsman if you haven’t seen it already. Besides seriously tailored suits and high-tech espionage, the film subtly sports a dark English humour amongst it’s cliche plot. Resting midway on the spy film parody scale with more a serious tone than say, Austin Powers.

Shaun of the Dead

When self-casted loser Shaun (Simon Pegg) finally realises the world has been taken over by the undead, he sets out to save his mum, his ex and drink until the zombie apocalypse passes. The film created the “zoo-rom-com” genre albeit the popularity of it’s successors like Warm Bodies and Night of the Living Deb. It hits all the marks for a lovely horror-comedy: light gore, deadpan dialogue and digs at true horror films. And no, it’s not a direct parody of Dawn of the Dead.

Horrible Bosses

Crude, sexual, and racial humour keeps the laughs coming during Horrible Bosses. The plot follows three friends who ultimately want to murder their, as the title shows, bosses. It’s unpredictable and relentless with a dark side that the cast portrays effectively. Props to Jennifer Aniston for her atypical role as a manipulating man-eater dentist whom I personally wouldn’t mind being harassed by. And Charlie Day for holding to his truly annoying yet riotous character. The plot twists, turns and will leave you wondering whether employees actually like you or not.

Bad Santa

Cinema was in need of a dark Christmas classic which was exactly what this deadpan film delivers. An alcoholic, disorderly, and quite repulsive Santa who robs department stores at the mall he’s working at each year. Aided by a Bernie Mac sidekick and troubled teen, the characters effortlessly synchronise with foul language, bad attitudes and crude, crude jokes. Needless to say, but you’ll either frankly despise or openly love Bad Santa.

The Big Lebowski

If you’re already a follower of His Dudeness, you need no explanation of The Big Lebowski’s greatness. A cult classic mastered by the Coen brothers where “The Dude” Lebowski simply wants his urine-drenched rug paid for and won’t stop until his financial retribution. There’s no punchlines, gags, or slapstick jokes. Just a peculiar, well-thought story of rejected morals, kidnapping, porn and the markings of everything a laid back, quintessential dude should be.

Pineapple Express


Don’t let the critical claims and teen hype for this pot-forward film strip you of all it’s glory. The plot follows two ridiculous stoners as they try to outrun a series of hitmen after witnessing a murder by their dealers boss. But what goes unseen by certain demographics is the amount of heart put into each character. Of course, it’s riddled with silly humour (nothing Will Ferrell fans aren’t used to), drug references and absurd action gags, but the magic lies in the depth of these charming performers that keep you watching, and laughing until close.


England’s criminal underworld has never seen an eclectic league of ordinary gentlemen like this before. When an 84 karat diamond goes missing, the series of events that trails brings a hodgepodge of unusual mates together in efforts to retrieve the goods. Catchy dialogue, dark humour and a convincing Irish gypsy Brad Pitt come together to portray a witty, enjoyable gangster-comedy film with spectacular cinematography.

National Lampoon’s Animal House

The college comedy that inspired later teen sex comedies we all know and laugh with today. If you’ve never seen National Lampoons Animal House (or any of the National Lampoon series), nows your chance to get started. The plot is straightforward, a bunch of rogue kids causing mishap on campus in ’62. But it’s historically accurate digs, classic party scenes and catchy scripts framed a milestone for comedic cinema and is worth having a watch for those who appreciate it.

Office Space

If you’ve ever hated your corporate desk job, watch Office Space. An entire deadpan comedy dedicated to the daily death of cubicle life in America, keeping us grateful for our current jobs… unless of course you’re in a cubicle.  The film follows Peter Gibbons as him and two friends rebel against an incompetent boss.It’s soundtrack was fuel for the swift popularity of “Damn, It Feels Good To Be A Gangsta”, and is known for the iconic company copy machine destruction scene.

Wet Hot American Summer

Those who opt for sketch comedy like Monty Python and The State are in for a treat. The film portrays a direct parody of 1980’s summer camp films and hits the mark with it’s coming of age jokes. Watch as these sexual, drug-loving counselours disregard their anticipated character development and become the reason your parents never sent you to day camp.


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