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The early 1990s saw a changing of the guard in Hollywood. With the box office success of comedy films on the rise, more and more comedians were breaking into show business and establishing themselves among the Hollywood elite.
This passing of the torch was best exemplified by none other than legendary funnyman Jim Carrey, who, after a flurry of box office knockouts, famously demanded a then-unprecedented $20 million to star in his next film, ‘The Cable Guy’. Despite all odds, this heavy-hitting comedian was quickly setting the standard for actors everywhere while simultaneously showcasing the money-making potential of the comedy genre.
An era of comedy defined by oddballs, dimwits, and egotists, the early ‘90s were chock-full of buddy comedies and parody. It was a time that ushered in the acting talents of many great comics, including Mike Myers, Tim Allen, and the late Chris Farley. Meanwhile, comedy mainstays like Bill Murray, Robin Williams, and Eddie Murphy continued to develop and keep the laughs steadily coming.
The ‘90s proved to be an experimental period for comedy films where countless upcoming comedians were given the chance to crack into stardom with their own unique brand of humor.
I explained it to you already, didn’t I? It’s a procedure. I’m learning all this as I go along. I’m bound to fuck up a little…
It’s easy to dismiss courtroom comedies. After all, the banality of our legal system doesn’t typically lend itself to a whole lot of laughter. Fortunately, however, Jonathan Lynn’s ‘My Cousin Vinny’ offers an impressive rebuttal to challenge that notion. It’s a film that is genuinely as smart as it is funny. This comedy classic is worthy of close-examination and offers a case that will have you cackling until the end.
Before you object to being badgered with anymore courthouse puns, allow me to present my sincerest testimony: ‘My Cousin Vinny’ is a criminally underrated film with unforgettable performances from its lead stars Joe Pesci and Marisa Tomei.
Pesci stars as the inexperienced New York attorney Vincent Gambini, who, despite having never stepped foot in a courthouse, must defend his wrongfully-accused cousin in a capital murder case. Vinny’s completely out of place in backwater Alabama, and he certainly isn’t the most qualified person for the task, but hey, he’s family!
Try as he might to heroically save his cousin from a trip to the electric chair, poor Vinny just comically can’t seem to catch a break. He’s in way over his head while caught between his nagging, know-it-all fiancée, and an uncompromising judge that has it out for him.
Vinny’s a hysterical ticking time bomb, with Joe Pesci being flawlessly cast for the role. Similarly, Marisa Tomei is superb as Vinny’s fiancée Mona Lisa Vito. She even managed to pull off a major (and controversial) Academy Award winning upset when she won the Oscar for Best Supporting Actress. With its talented cast, absurd circumstance and smart humor, ‘My Cousin Vinny’ is a unique and laudable gem of a movie.
I want the whole universe to behold this transfer of power. No longer will our future society be based on the ideas and the music of these two fools! They will be based on my ideas, and my ideas alone!
Anyone fortunate enough to have seen the ‘Bill & Ted’ movies is sure to agree that high school bandmate boneheads Bill S. Preston, Esquire and Ted ‘Theodore’ Logan are among the quintessential ‘90s comedy duos. These two metal-head dimwits may seem like talentless musicians in the present, but they are destined to one day become the greatest band the universe has ever seen, as foretold by a time-traveler from the future named Rufus.
After narrowly passing their high school history class in their most excellent first adventure, Bill and Ted remain together with their band Wyld Stallyns now one step closer to reaching their destiny. However, things take a most unexpectedly bogus turn in this sequel when they find themselves dead. They’ll have to fight their way through Hell in order to make it back to Earth to secure the future.
First and foremost, ‘Bill & Ted’s Bogus Journey’ is a much smarter comedy than you might think. It even features a fantastic parody of Ingmar Bergman’s ‘The Seventh Seal’. Despite Bill and Ted’s ignorant stupidity, their movies are as creative and clever as they are comical.
Alex Winter and Keanu Reeves make for a wonderfully amusing pair, as Bill and Ted respectively, in a role that Keanu Reeves once feared he’d never be able to escape. George Carlin also delights in his return as Rufus. ‘Bogus Journey’ is a truly unique adventure that traverses both Heaven and Hell, while also giving us a glimpse of the harmonious utopian future that is one day derived from the legendary music of Bill and Ted.
What would you do if you were stuck in one place and every day was exactly the same, and nothing that you did mattered?
How would you like to wake up and relive the same day of your life over and over again? That’s exactly the pickle weatherman Phil Connors (Bill Murray) finds himself in during his trip to Punxsutawney for the yearly Groundhog Day festivities. For the fourth year running, Phil is assigned against his will to cover this inane annual holiday, and he couldn’t be more annoyed about it. Just when he thinks this day couldn’t be any worse, he wakes up the next day to find himself reliving it. Again and again, Phil wakes up on the morning of Groundhog Day, stuck in Punxsutawney, and trapped in a seemingly endless cycle. In a world without tomorrow, Phil Connors lives a life without consequences, but he soon discovers that this unique position provides him with unlimited chances to make the best of his situation and live his life to the fullest.
‘Groundhog Day’ is undoubtedly some of Bill Murray’s finest work. He is both comical with his cynicism and captivating with his charm. His grumpy, self-centered character becomes even more hilarious as he teeters on the verge of losing his sanity due to the inescapable repetition of his life.
It’s an entertaining and humorous experience to watch as this dreadful and egotistical person tries to find new ways to escape his own perpetual Hell. Yet it’s even more satisfying to watch his character grow and evolve from a sarcastic Scrooge into a well-rounded, good-natured human being. With ‘Groundhog Day’, director Harold Ramis delivers a dark comedy that is bold, clever, and worthy of many, many repeat viewings.
Have you ever had that feeling that this is the best I’m ever gonna do, this is the best I’m ever gonna feel… and it ain’t that great?
What better way to face a midlife crisis than by heading out into the Old West for a ride off into the sunset? Well, at least that’s how Mitch Robbin’s best friend and brother reckon it. For Mitch’s 39th birthday, the two of them present him with an opportunity to grab (or lasso) life by the horns.
Unpleased with his mundane, middling, everyday city life, Mitch agrees to join his two best friends on a guided two-week cattle drive where the three of them can learn to live like true cowboys and perhaps find some deeper meaning in their lives.
‘City Slickers’ is a fun-filled comedy with plenty of laughs and a whole lot of heart. These three aspiring temporary cowboys make for a memorable trio, with Daniel Stern being a hilarious scene-stealer as Mitch’s uptight best friend Phil. Billy Crystal, as Mitch Robbins, is comically relatable with his sarcastic and unenthusiastic approach to life on the frontier.
His two best friends, on the other hand, are eagerly embracing the ways of the Wild West, despite being a pair of city boys without a clue. Led by the mysterious and intimidating cowboy Curly, played expertly by Jack Palance, these three amigos have to get their act together and cowboy up in order to make it through this rodeo.
Hit me! Just give it to me straight! I came a long way just to see you Mary. The least you can do is level with me. What are my chances?
I’d be remiss to talk so much about Jim Carrey in the introduction and not include one of his movies on this list. ‘Dumb & Dumber’ is Carrey at his best, and is arguably one of the funniest slapstick comedies ever made.
This Farrelly Brothers’ film is so effective and thorough in its stupidity that it is nothing short of remarkable. Jim Carrey and Jeff Daniels give up their brain cells and give it their all with uproarious performances that make them a perfect comedy pair.
The film features two lovable dimwits in Lloyd Christmas (Carrey) and Harry Dunne (Daniels) who take a cross-country road trip looking to reunite Lloyd with his all-too-brief love. The two of them embark for Aspen, Colorado in search of the lovely Mary (Slippy? Slappy? Samsonite!) Swanson, and their friendship is put to the ultimate test when Harry falls head over heels for her, too.
All the while, these dummies are unknowingly mixed up in a dangerous ransom and are being pursued by a pair of hitmen. Jealousy, revenge, and hilarity ensue as Harry and Lloyd compete for the love of a woman they hardly know.
General, are you telling me that nowhere in the military is there any longer a job for trained human weapons of destruction such as myself?
Major Benson Winifred Payne is a heavily-trained, cold-blooded, military combat killing machine. The only problem is, there’s no one left for him to kill. Thus, the Marines have no choice but to discharge him from service.
In an effort to help him readjust to civilian life, Payne’s placed in charge of a JROTC program at a nearby school. It’s Rambo meets Kindergarten Cop when Major Payne arrives. He’ll have two months to turn these lazy, disobedient kids into upstanding, disciplined cadets. Major Payne will give them Hell, and they’ll band together to give him a war.
This teacher versus student comedy is filled to the brim with great pranks and some unbelievably funny insults. Damon Wayans is enthralling as Major Payne, in what is no doubt the funniest movie role of his career. He’s a brilliant combination of testosterone, sternness, and peculiarity.
Payne is virtually incapable of seeing life beyond the battlefield, and he demands the same level of inhuman dedication and discipline out of his less-than-enthusiastic students. The two opposing sides will have to learn to deal with each other or else they might just kill each other. ‘Major Payne’ is a laugh-out-loud war that will warm your heart with its ultimate amendment of respect and understanding.
Hey if you’re going to say I didn’t put the right kind in, you’re wrong. I used 10-W-30. And besides, motor oil would have nothing to do with this accident…
Saturday Night Live star Chris Farley burst onto the big screen in the early 90s, quickly becoming one of the decade’s most unique and beloved stars. He was the definitive man-child – one who would shed his gentle demeanor at the drop of a hat with fits of rage.
He was the short-tempered, lovable oaf who contrasted his overweight size with a relentless display of energy and athleticism. Despite his much-too-soon death in 1997, Farley distinguished himself as one of the most unforgettable comedians of the ‘90s.
Chris Farley landed his first starring role in ‘Tommy Boy’ alongside fellow SNL comedian David Spade, creating what would become an unlikely and inseparable comedic pair.
The film features Farley as Tommy, the childish, dim-witted son of an auto parts factory owner. When his father dies suddenly from a stroke, it’s up to Tommy to take over the family business and keep the factory from going under. With the help of his deceased father’s assistant Richard, as played by Spade, Tommy has to learn the ropes of the business world while hitting the road to sell his father’s products.
While the premise of ‘Tommy Boy’ may be a bit formulaic, the journey in this coming-of-age comedy is an enjoyably disastrous affair. Farley’s Tommy fumbles and rages through just about every possible opportunity, much to the chagrin of his snarky sidekick Richard. This spoiled, irritable, bumbling idiot is Farley at his best, and he’s perfectly contrasted by David Spade’s arrogant, experienced character.
Travis, it really tweaks my melon, to see a buff bro like Crawl here, get weezed on by a greasy scumbag like you…
Pauly Shore may be long forgotten these days, but back in the ‘90s, he was all over the airwaves. With his own variation of surfer/stoner lingo, he became a poster boy for a party-heavy MTV culture.
It wasn’t long before The Weasel made it into the movies. Despite his films being generally abhorred by critics, Pauly’s movie career wasn’t a complete failure, and a couple of his films became eventual cult classics. For one such example, look no further than 1993’s ‘Son in Law’, in which Pauly plays an eccentric California party animal named Crawl who falls in love with country girl college dorm-mate Becca who invites him to stay with her at her parent’s farm for Thanksgiving. Coming from two seemingly opposite worlds, Crawl and Becca’s parents have to learn to get along if he ever expects to have any chance of one day becoming their future son-in-law.
‘Son in Law’ is a cute and pleasant fish-out-of-water story that contrasts Crawl’s strangeness with Becca’s family’s straightness. While they make for an unlikely match, Becca’s family can’t help but find Crawl’s peculiarities rubbing off on them. Even though he’s unlike anyone they’ve ever met, they soon learn to see the good guy beneath his oddball exterior and accept him like he’s one of their own.
Pauly Shore is not only hysterical in ‘Son in Law’, but also bizarrely charming and relatable in his own unique and goofy way. Love him or hate him, there has never been another like him – this is Pauly Shore at his finest.
Tell everyone that when the day is out we shall have a wedding. Or a hanging. Either way, we’re gonna have a lot of fun, huh?
Before the incomparable parody king Mel Brooks retired from directing, he gave us one last great comedy film with ‘Robin Hood: Men in Tights’. This Robin Hood parody particularly pokes fun at the 1991 film adaptation ‘Robin Hood: Prince of Thieves’, starring Kevin Costner.
‘Men in Tights’ is a silly, light-hearted, fourth-wall-breaking, musical comedy that sees Robin Hood (as played by Cary Elwes) battle the Sheriff of Rottingham as he attempts to dethrone corrupt despot Prince John and win the heart of the lovely Maid Marian.
Complete with a talented and comical ensemble cast that includes Richard Lewis, Tracey Ullman, Mel Brooks, and Dave Chappelle (in his first ever movie role), ‘Robin Hood: Men in Tights’ is a pleasurable romp from beginning to end.
Elwes is dashing and delightful in his humorous portrayal of Robin Hood, combining his cheeky delivery with ineptitude and arrogance. Richard Lewis nails his part as the whiny, bratty, immature, placeholder ruler Prince John. The Merry Men trio of Blinkin, Achoo, and Little John are exceptionally funny supporting characters responsible for much of the film’s many laughs. All in all, ‘Robin Hood: Men in Tights’ is a fun spoof of the classic tale that the whole family can enjoy.
I’m happy for you, kid. But if you think you can hurt me again, you’re wrong. I left my heart in my other pants…
Long before the tiger’s blood, drug scandals, and the HIV reveal, Charlie Sheen was on the road to becoming an undisputed comedy movie legend. This was never more apparent than in ‘Hot Shots: Part Deux’, the Rambo-inspired sequel to ‘Hot Shots’, when Sheen was in his physical and comedic prime.
The film is a parody of the macho action movies of the ‘80s that starred actors such as Stallone and Schwarzenegger. Sheen plays Topper Harley, a retired war hero called back into action to rescue POWs in Iraq. Along the way he’ll reunite with the love of his life, fight alongside the incompetent President of the United States, and go head-to-head with the villainous dictator Saddam Hussein.
‘Hot Shots: Part Deux’ is riddled with clever jokes and quick laughs, with comedy so stupid you can’t help but smile. Nothing is off-limits in this action-inspired parody, with dozens of movie references ranging from ‘Terminator 2’ to ‘The Lady and the Tramp’. There’s even a brilliant meta movie moment featuring a cameo from Sheen’s father, actor Martin Sheen.
Charlie Sheen is outstanding as Topper, with impeccable timing and delivery. He demonstrates the presence of a true leading Hollywood star. Meanwhile the legendary Lloyd Bridges is a major standout as President Benson, in what was one of the final movie roles of his career.
‘Hot Shots: Part Deux’ is an underrated classic that will likely make you wish Sheen’s film career had lasted a little longer, but also make you grateful in knowing that he was ultimately able to recover.
The early ‘90s were a special time for the comedy genre. They ushered in the rise of so many of today’s most distinguished and beloved legendary comedians and transformed many upstart comics into unforgettable stars.
The ‘90s offered comedy that was classy in its character and intelligent in its inanity. This largely innocent era is a far cry from the vile and tasteless content of popular comedy in the decades that have since followed. It was a period that thrived in originality and good old-fashioned fun, as movie-makers were willing to gamble in the hopes of creating another long-lasting star.
Cool article man. Digging the black hair.
Thanks, Dominic! I appreciate it!
Wow, I love this Article! :) It reminds of how great comedy in the 90’s was. I am so happy Tommy Boy made the list, that movie was great! :)
Thanks so much, Lana! Yeah, the 90s are my favorite movie decade, especially with comedies. They just don’t make them like they used to! I’m glad you also enjoy Tommy Boy, and I hope you’ll check out some of the other films on the list!