90’s Comedies That Could Not Get Made Today

The 90’s was an amazing time for movies and TV and there were a huge amount of great comedies released, including many that just could not get made today. Comedies that may well make you cringe for their very non-pc moments but they still have a lot of laugh out loud moments. Take a look at this list and see how many you have seen:

TommyBoy (1995)

“Tommy Boy” follows the misadventures of Thomas “Tommy” Callahan III (Chris Farley), a good-natured, but socially awkward and clumsy man-child. After seven years of barely making it through college, Tommy returns home to his father’s (Brian Dennehy) auto parts factory in Sandusky, Ohio.

However, upon his arrival, Tommy discovers that the family business is in deep financial trouble and is at risk of being taken over by the conniving Ray Zalinsky (Dan Aykroyd). Determined to save his father’s legacy and the jobs of the factory’s loyal employees, Tommy teams up with his father’s sarcastic and cynical assistant, Richard Hayden (David Spade).

Together, the oddball duo embarks on a hilarious cross-country sales trip to sell a new line of brake pads in a last-ditch effort to save the factory. Their journey is filled with mishaps, outrageous humor, and heartwarming moments as they navigate through various comedic situations.

“Tommy Boy” is a classic comedy that showcases Chris Farley’s physical comedy talents and the comedic chemistry between Farley and David Spade. The film combines slapstick humor with heartfelt moments, making it a beloved cult favorite among comedy fans.

Happy Gilmore (1996)

“Happy Gilmore” follows the story of Happy Gilmore (played by Adam Sandler), an aspiring ice hockey player with a powerful slap shot but a complete lack of skating skills. After his grandmother’s house is threatened with foreclosure due to unpaid taxes, Happy discovers that he has an uncanny talent for hitting golf balls with tremendous power and accuracy.

Determined to save his grandmother’s home, Happy decides to use his golfing skills to enter professional tournaments and earn enough money to pay off the debt. However, his unorthodox and often brash playing style clashes with the traditional golfing norms, leading to conflicts with other players, particularly with the snobbish and arrogant golfer Shooter McGavin (played by Christopher McDonald).

As Happy rises through the ranks of professional golf, he gains both supporters and detractors, including a feisty public relations executive named Virginia Venit (played by Julie Bowen) who sees potential in Happy’s unconventional persona. Throughout the film, Happy faces numerous challenges on and off the golf course, and he must learn to control his temper and harness his talents to become a better golfer and a more mature individual.

As the climactic tournament approaches, Happy must confront Shooter McGavin in a final showdown to determine the future of his grandmother’s house and secure his place in the golfing world.

American Pie (1999)

“American Pie” is a popular teen comedy film released in 1999, directed by Paul Weitz. It follows the story of four high school friends on a quest to lose their virginity before their senior prom. The film became a cultural phenomenon and spawned several sequels and spin-offs.

The film centers around Jim Levenstein (played by Jason Biggs), an awkward and sexually inexperienced high school student who makes a pact with his three best friends: Kevin Myers (Thomas Ian Nicholas), Chris “Oz” Ostreicher (Chris Klein), and Paul Finch (Eddie Kaye Thomas). The pact is to lose their virginity before their senior prom.

Throughout the movie, each of the four friends embarks on their own humorous and sometimes embarrassing attempts to achieve this goal. Jim, in particular, has numerous hilarious mishaps in his pursuit of sexual experience, often resulting in awkward and embarrassing situations. Meanwhile, Kevin tries to rekindle a relationship with his ex-girlfriend, Vicky (Tara Reid), while Oz attempts to impress a girl named Heather (Mena Suvari) by joining the school’s lacrosse team.

The film also introduces Steve Stifler (Seann William Scott), an obnoxious and crude character who becomes the comic relief and adds to the misadventures of the group. Stifler’s antics often lead to both humorous and uncomfortable situations for the group.

As the prom approaches, the friends face challenges and revelations about themselves and their relationships, which eventually lead to some heartwarming and memorable moments. In the end, they come to realize that their experiences and friendships are more important than just losing their virginity.

Milk Money (1994)

“Milk Money” is a heartwarming comedy-drama directed by Richard Benjamin. The story revolves around three 11-year-old boys: Frank Wheeler (played by Michael Patrick Carter), Brad (played by Brian Christopher), and Kevin (played by Adam LaVorgna).

Frank and his friends are curious about sex and girls but are still quite innocent. They decide to pool their money together to see a naked woman for the first time. So, they sneak into the city, where they meet V (played by Melanie Griffith), a street-smart and good-hearted prostitute.

In a twist of fate, the boys end up witnessing a crime, and V takes them under her wing to protect them from the dangerous criminal involved. She decides to take the boys back to their suburban neighborhood, where they pose as her nephews to avoid suspicion.

V ends up staying with Frank’s single father, Tom Wheeler (played by Ed Harris), and tries to pass off as a math tutor to the boys’ friends and neighbors, while keeping her true profession a secret. Along the way, she learns about the struggles and complexities of suburban life, and a tender bond forms between V and Tom.

Ace Ventura: Pet Detective (1994)

“Ace Ventura: Pet Detective” is a comedy film released in 1994, directed by Tom Shadyac and starring Jim Carrey in the lead role as Ace Ventura. The film follows the adventures of Ace Ventura, a quirky and eccentric private investigator who specializes in retrieving lost or stolen pets.

Ace Ventura is renowned for his unique and unorthodox methods of finding missing animals, and he has earned a reputation as the best pet detective in Miami. When a rare and valuable dolphin named Snowflake is kidnapped from the Miami Dolphins football team, their mascot and good luck charm, the team’s owner hires Ace to track down the missing dolphin and bring it back before a crucial football match.

As Ace delves into the case, he encounters a series of hilarious and outrageous situations. With his unconventional investigative skills, including his mastery of animal behavior and unique disguises, Ace follows the trail of clues, leading him through a wild and zany journey.

During his investigation, Ace encounters colorful characters, including the team’s suspicious manager, the beautiful and mysterious publicist, and various bizarre suspects. His humorous antics and absurd methods bring both laughter and chaos, captivating the audience along the way.

As the plot unfolds, Ace gradually unravels the truth behind the kidnapping and uncovers a surprising conspiracy involving the Miami Dolphins. The film culminates in a climactic showdown, where Ace must use all his skills and eccentricities to save Snowflake and reveal the culprits behind the dolphin’s disappearance.

Big Daddy (1999)

“Big Daddy” is a 1999 comedy film directed by Dennis Dugan and starring Adam Sandler. The movie revolves around the life of Sonny Koufax (played by Adam Sandler), a lazy and irresponsible 30-year-old man who lives off a lawsuit settlement from a minor accident.

Sonny’s life takes an unexpected turn when his girlfriend leaves him, feeling fed up with his lack of ambition and maturity. Around the same time, a young boy named Julian (played by twins Cole Sprouse and Dylan Sprouse) shows up on his doorstep, claiming to be the biological son of his roommate and friend Kevin. Julian’s mother, whom Kevin had a one-night stand with, is now facing legal troubles, and Kevin is out of town for a business trip.

Initially overwhelmed by the responsibility, Sonny decides to care for Julian temporarily until Kevin returns. However, as time passes, Sonny starts to bond with Julian and realizes the joys and challenges of parenthood. He adopts the nickname “Big Daddy” and attempts to provide the boy with a fun and unconventional upbringing, often resorting to comedic and offbeat parenting methods.

As Sonny gets more involved in Julian’s life, he also starts to reevaluate his own. He discovers a newfound sense of purpose and maturity, understanding the importance of being a responsible adult and caring for others.

Never Been Kissed (1999)

“Never Been Kissed” is a romantic comedy film released in 1999. The movie stars Drew Barrymore as Josie Geller, a 25-year-old copy editor for the Chicago Sun-Times who dreams of becoming a successful reporter. Josie is highly intelligent and dedicated to her work, but her social life has been less than fulfilling.

Assigned to go undercover as a high school student to research a story on the teenage experience, Josie gets a chance to relive her high school years and correct the mistakes she made the first time around. However, as she tries to fit in with the popular crowd and rediscover her teenage self, she faces numerous challenges and insecurities. Josie finds herself struggling to balance her journalistic integrity, developing friendships, and navigating romantic interests.

Josie’s brother, Rob Geller (David Arquette), who was popular in high school, joins her undercover operation to support her and ensure her safety. As she navigates the halls of high school, Josie realizes the complexities of teenage life and how different it is from her memories. Despite the challenges, Josie’s quirky and endearing personality eventually wins over some of her classmates.

During her time undercover, Josie develops a romantic interest in her English teacher, Sam Coulson (Michael Vartan). As she wrestles with her feelings for Sam and the ethics of her journalistic assignment, she starts questioning her true identity and desires.

As the story unfolds, Josie learns valuable life lessons, gains self-confidence, and forms meaningful connections with her classmates. However, things take a dramatic turn when her cover is blown, and her true identity as a reporter is exposed in front of the entire school.

In the climax, Josie must confront the consequences of her actions, mend broken relationships, and take a stand for what she believes in. The film concludes with a memorable prom night, where Josie finally experiences her long-awaited first kiss in a romantic and heartwarming moment.

“Never Been Kissed” explores themes of self-discovery, acceptance, and the importance of being true to oneself, and it delivers a heartwarming and humorous tale of second chances and finding love in unexpected places.

The Waterboy (1998)

“The Waterboy” is a popular American sports comedy film released in 1998. The movie stars Adam Sandler in the lead role as Bobby Boucher, a socially awkward and stuttering waterboy for the South Central Louisiana State University (SCLSU) football team.

Bobby Boucher is a simple-minded but kind-hearted waterboy for the SCLSU Mud Dogs, a struggling college football team. Despite his dedication to providing water to the players, Bobby is often mistreated and ridiculed by both the players and the coaching staff due to his constant stutter and lack of social skills.

One day, during a practice session, Bobby gets fed up with the constant abuse and unleashes an unexpected burst of anger, showcasing his untapped talent as a ferocious tackler. The team’s coach, Coach Klein (played by Henry Winkler), notices Bobby’s hidden football abilities and decides to recruit him as a linebacker for the Mud Dogs.

Bobby’s newfound football skills quickly make him a star player, and the team’s fortunes start to turn around. He becomes an essential part of the team and leads them to a series of improbable victories. Along the way, Bobby also starts to gain self-confidence and begins to come out of his shell.

However, his overprotective and controlling mother, Mama Boucher (played by Kathy Bates), disapproves of his involvement in football, fearing it will lead to his injury. As the Mud Dogs progress towards the championship game, Bobby must confront his mother’s fears and the challenges that come with newfound fame and success.

“The Waterboy” is a hilarious and heartwarming story that revolves around football, personal growth, and the power of believing in oneself. It was a commercial success and further established Adam Sandler as a popular comedy actor in Hollywood.

Austin Powers: International Man of Mystery (1997)

Austin Powers: International Man of Mystery is a comedy film released in 1997, directed by Jay Roach and starring Mike Myers in the titular role. Here’s a synopsis of the movie:

The film revolves around the character of Austin Powers, a swinging 1960s British secret agent known for his groovy style and womanizing ways. Powers is frozen in a cryogenic chamber in the 1960s by his nemesis, Dr. Evil (also portrayed by Mike Myers), an eccentric and comically evil villain with plans of world domination.

Fast forward to the 1990s, where Dr. Evil returns and threatens the world with a doomsday device. The British Secret Service decides to unfreeze Austin Powers, believing he’s the only man who can stop Dr. Evil. Powers, who’s hopelessly outdated and completely out of touch with the modern world, is reintroduced to the swinging ’90s, and his humorous antics ensue as he struggles to adapt to the changes in society and technology.

With the help of his attractive sidekick, Vanessa Kensington (played by Elizabeth Hurley), daughter of his former partner, Austin Powers sets out to foil Dr. Evil’s evil plans. Along the way, they encounter a variety of hilarious and absurd characters and situations, all while paying homage to the spy genre and the 1960s pop culture.

Throughout the movie, Austin Powers delivers iconic catchphrases and engages in over-the-top action sequences that parody classic spy films like James Bond. The film combines witty humor, slapstick comedy, and clever references to create a cult classic that has continued to entertain audiences for years.

South Park: Bigger, Longer, and Uncut (1999)

“South Park: Bigger, Longer & Uncut” is a 1999 animated musical comedy film based on the popular TV show “South Park.” The film was directed by Trey Parker and follows the same comedic style and irreverent humor as the series.

The story begins in the small, fictional Colorado town of South Park, where four foul-mouthed boys, Stan Marsh, Kyle Broflovski, Eric Cartman, and Kenny McCormick, are eagerly anticipating the release of a new R-rated Canadian movie called “Terrance and Phillip: Asses of Fire.” The movie features their favorite crude humor duo, Terrance and Phillip, who frequently engage in inappropriate and vulgar antics.

The boys sneak into the movie despite its adult rating, and their minds are corrupted by its crude content. As a result, they start using profanity and obscenities, which upsets their parents and teachers. The parents of South Park, led by Kyle’s mother, Sheila Broflovski, form a campaign to ban Terrance and Phillip and blame Canada for corrupting their children.

Their efforts escalate when the United States government, fearing war with Canada, pressures the execution of Terrance and Phillip for their influence on American children. Meanwhile, Satan and his lover, Saddam Hussein, are planning to take over the world, with Saddam determined to conquer Canada as well.

The boys realize the gravity of the situation and decide to take matters into their own hands. They, along with their schoolmate Wendy Testaburger, embark on a mission to save Terrance and Phillip and prevent a war between the United States and Canada. The adventure takes them to a bizarre journey through various locations, including Hell itself.

Throughout the film, the story explores themes of censorship, freedom of speech, and the impact of media on society, all while delivering a plethora of crude humor, satirical commentary, and catchy musical numbers.

As the plot unfolds, the boys encounter numerous absurd and hilarious situations, blending satire and social commentary with the show’s characteristic crude humor.

“South Park: Bigger, Longer & Uncut” received critical acclaim for its sharp wit, musical numbers, and unapologetic humor. Despite its controversial content, it is often praised for its intelligent satire and commentary on societal issues. The film remains a beloved cult classic among fans of “South Park.”

What did you think of this list? Which comedy films would you have added?