There are certain films that practically every movie fan has seen or at least heard of, and that’s never more true than with the comedy movies of the 1990s. Whether they were smash-hit blockbusters that saw a new lease of life on VHS, DVD, and streaming, or critically acclaimed masterpieces whose quality will always attract an audience. This group of pictures will stay relevant for generations to come – even if the comedy movies of the ’90s did have some cringe moments.

It’s impossible for any ’90s comedy movie to be fully forgotten if it’s been committed to film, because there is always a chance it was somebody’s favorite childhood film, or a huge cinephile found it during their extensive research of movies throughout the ages. The 1990s were a treasure trove of comedy classics, some much more long-lasting than others, from the best romantic comedies of the ’90s to the classic teen comedies of the ’90s. Though many people might have seen them once or twice, they haven’t quite reached the cult status that some other films of the decade have managed to do.

10

Trading Mom (1994)

Directed by Tia Brelis

Times were very different in the 1990s (that’s no surprise) and the market for movies made for younger audiences was rife. Families took trips to the cinemas together, and home video releases were very popular, with kids collecting their favorite tapes to watch whenever they could. Nowadays, a phone with internet access allows for unlimited viewing, and films like Trading Mom are being made less and less. Whether it’s a good or bad thing is up for debate. Some might remember watching this nostalgic gem with their parents or friends, and it’s one of those films that unlocks core memories.

The premise is relatable and follows a group of siblings who feel frustrated with their mom and decide to swap her for a modified model. The alternative тιтle is The Mommy Market, which is where they find these new versions (all played by Sissy Spacek). As expected, it turns out the mom they have is genuinely the best, and it gives them a newfound appreciation for their loving parent. It’s a message that is definitely worth reminding. A post My Girl Anna Chlumsky also stars.

9

Detroit Rock City (1999)

Directed by Adam Rifkin

Having a quest at the center of the plot allows for some entertaining comedy hijinx, as the viewers journey along with the heroes to get to their chosen destination. In this instance, the place to be is a KISS concert, and the heroes are a group of rebellious teens who escape their overbearing households in hopes of seeing their favorite rock band perform. It’s set in the ’70s and features a lot of music by the legendary band, and even sees them co-star in the film.

In addition to the many obstacles the boys have to overcome in order to reach their goal, the movie shows just how important a role music plays in people’s lives. It’s not just a vehicle for rebellion for young people, but it serves as a soundtrack to all the stages of one’s life. Despite a very relatable premise, great score, and celebration of nostalgia, the film failed to set the box office alight, meaning it didn’t necessarily reach as many people as it should have. But, this forgotten gem is genuinely worth a watch.

8

Little Giants (1994)

Directed by Duwayne Dunham

Little Giants may have been a film intended for younger children, but it has a message that is important to this very day. Ed O’Neil and Rick Moranis provide the star power to keep the older viewers entertained, as the plot follows rival peewee football teams that compete for the right to represent their district in the official league. The reason that there are two teams is that a talented young girl is not allowed to play alongside the boys on the team.

One team is made up of varsity types who also have the tendency to bully those who are deemed weaker or lesser-than, while the other is formed of scrappy outcasts who just want to be part of something special. Bearing in mind this film was made in the early ’90s, there are so many positive messages about inclusivity and giving people a chance, it feels relevant now more than ever. Devon Sawa’s extreme ’90s curtain haircut encapsulates the era perfectly.

7

Airheads (1994)

Directed by Michael Lehmann

The 1990s are well-known for leaning into teen counterculture and saw the rise of “slacker” comedies. With strong satirical elements, highlighting the absurdity of the music industry, Airheads manages to make a statement while also making the audience laugh. The dynamic trio of Brendan Fraser, Steve Buscemi, and Adam Sandler forms a heavy metal band called “The Lone Rangers”, who are desperate to make it big on the music scene. After facing a lot of rejection and heartbreak, they decide to take over a radio station in order to get their record played.

It’s not just a metaphorical takeover that involves a run-of-the-mill guest co-hosting spot, but rather a hostage situation. What ensues is a clash of corporate protocols and rebellious anarchy which sums up the sentiment of the movie really well. The band gains media attention, but the cost is very high, and it leads them to question whether such exposure is a negative influence on their artistic vision. With similar issues affecting many musicians today, this nostalgic comedy still holds up.

6

Dick (1999)

Directed by Andrew Fleming

The Watergate scandal has had many outings in cinema. All the President’s Men and Frost/Nixon looked at it through a serious lens, and Forrest Gump took some liberties, as it did with many other historical events. But, Dick manages to completely reimagine this infamous moment in time. Kirsten Dunst and Michelle Williams play a couple of sweet but slightly shallow teenagers, who somehow end up being the ones to uncover the cover-up and bring down a powerful president.

Rewriting history through comedy is always fun to watch, as viewers get to enjoy the creative ways of making actual facts fit into the story being told onscreen. The seemingly ditzy girls are ultimately able to outsmart a lot of influential political figures, and the film does a great job of showcasing the pitfalls of a corrupt government. The callbacks to the 1970s are also a treat, with some great music, authentic set decor, and fashion.

5

Jawbreaker (1999)

Directed by Darren Stein

While this film has certainly built a cult audience, and there are those who would consider it their absolute favorite teen film of all time, it’s important to note that it does not quite have the same name recognition as Clueless or Cruel Intentions. But, this dark comedy dressed up in bright colors is a delicious showcase of what made this daring decade so great. Playing on themes of popularity, and the extremes people would go to achieve it, it tackles some truly heavy themes hidden behind a killer soundtrack.

Rose McGowan is one of the most iconic mean girls in teen movie history, as she delivers some vicious lines with the sweetest fake smile. Judy Greer also does a great job in a very “Judy Greer” type of role, and the costumes are nothing short of award-worthy. While some films of the same genre might try and deliver a hidden message that’s saccharine and cheesy, Jawbreaker does not stoop to those levels. While the villain may get punished, it still has an edge that it shares with its 1980s predecessor, Heathers.

4

Honeymoon in Vegas (1992)

Directed by Andrew Bergman

Before Nicolas Cage got his Academy Award for Leaving Las Vegas, he headed to Sin City to marry his longtime love, played by Sarah Jessica Parker. Neither actor had reached their peak of fame when this underrated gem came out, and the biggest star of the picture was James Caan. The love triangle that occurs between the three fabulous actors is truly fun to watch, as the action takes viewers from Vegas to Hawaii and back again.

There is a dash of typical neuroses and ennui, especially evident in the cynical Jack Singer, who is haunted by a deathbed request that causes a lot of tension in his relationships. When he’s finally a step closer to committing to Betsy, a suave businessman steps in to wreak havoc on their plans to elope. With some laugh-out-loud moments, as well as a smidgen of deception, there is a lot to like about Honeymoon in Vegas. The opening animation, Bruno Mars’ short and sweet cameo, and some skydiving Elvises are only a few of the highlights to look out for.

3

But I’m a Cheerleader (1999)

Directed by Jamie Babbit

The humor in this ’90s indie classic is dark and scathing, as it satirizes the idea of forcefully imposing gender norms and conformity on a group of LGBTQ+ youths. Set at a conversion camp, it follows a seemingly bubbly cheerleader who is suspected by her parents of being a lesbian, and in need of being “cured”. But, what actually happens at the camp is her finding a meaningful romantic connection, and more importantly, finding her true self.

Satire is certainly at the heart of the film as it uses the stereotypical ᴀssociation of colors like pink and blue to reinforce hetero-normative gender conventions. There is also a focus on the “traditional” behavior expected of the feminine and masculine characters, as they are put in a variety of ridiculous situations in order to help “de-program” them. It’s a film that holds up to this day, with some witty and moving performances from Natasha Lyonne, Clea DuVall, and Melanie Lynskey.

2

Singles (1992)

Directed by Cameron Crowe

Very much in the vein of Reality Bites and Empire Records, this slightly less well-known project similarly follows a group of young people trying to find their way in the world. Part of Cameron Crowe’s impressive early body of work, it captures the feeling of uncertainty that many twentysomethings feel, but dresses it in plaid and combat boots for a suitably grunge feel. The Seattle setting adds even more credence to the rebellious and anarchic feeling that this movement invoked at the time. This is further fortified by the soundtrack and music moments throughout the film.

Bridget Fonda’s wide-eyed portrayal feels relatable to this day, and the romantic entanglements also hit close to home despite the very different way the dating scene looked back then. There are some bittersweet laughs, and a lot of food for thought. While it didn’t stand the test of time the way some other similar films of the era did, it has a lot to offer and is definitely worth rediscovering.

1

Can’t Hardly Wait (1998)

Directed by Harry Elfont and Deborah Kaplan

Similarly to Jawbreaker, this film is unlikely to have been forgotten by true fans of the genre, and those who grew up being raised by TV and film. But, for the casual viewer, or one who rarely re-watches films of the past, this brilliant teen comedy might have slipped through the net. The cast reads like a who’s who of ’90s stars, and includes Jennifer Love Hewitt, Seth Green, and even the teenage witch herself, Melissa Joan Hart, in an uncredited role, that has more lines than many of the credited ones.

As a group of recent graduates enjoys one last big high school party, the film follows different groups who all have their own storylines, each more fun and entertaining than the other. There is a shy guy pining for the homecoming queen, a very culturally inappropriate group with a goal of losing their virginity, and even a washed-up ex-football captain who provides a much-needed reality check for those who peaked in high school. In addition to being very funny, it’s just so fun to try and spot all the famous faces in the background.