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10 Essential Comedy Movies From 1995

August 23, 2025 by Tom Jolliffe

It’s laughs aplenty with these ten essential comedies from 1995… 

When life gives you lemons and you have no clue how to make lemonade, sometimes you need to brighten your mood another way. Step forward the humble comedy film, where you’ll hopefully spend the best part of 90 minutes laughing until your ribs ache. Or, you could watch Slam Dunk Ernest.

To the chagrin of many, comedy films aren’t as frequently made or as amusing as they used to be. It’s a genre deemed largely irrelevant as a big-screen enterprise. Once a former deity of big screen comedy, Adam Sandler has recently been repackaged as a prolific deliverer of straight-to-Netflix specials, not least his recent (long-awaited) sequel, Happy Gilmore 2. The original film represented his firm establishment of box office pedigree, and this follow-up shows just where Sandler and the genre stand currently.

Travelling back 30 years to a period that saw the Sandman, Jim Carrey and more become champions of the genre and money-spinning box office behemoths, shows big screen comedy lovers were well served with limitless options. Here are ten essential comedy films from 1995…

Billy Madison

Speaking of the Sandman, before his hugely successful golfing comedy the following year, his first big breakout came in 1995, with Billy Madison. Sure, Rodney Dangerfield had kind of covered the concept a decade earlier with Back to School, but with Madison, Sandler perfected his man-child persona starring as an uneducated shlub. He’s sent back to elementary school and tasked with passing if he hopes to inherit his family business.

Cue the comical sight of Sandler sat next to small kids, uncomfortably stuffed into the tiny chairs and tables and getting outsmarted by the booger-ridden little oiks. Along the way, he falls in love with one of the teachers and gets into all manner of comical situations. Scattergun in its approach and filled with sight gags, immature humour and prat falls, it’s the formula that Sandler has rarely strayed from, and here at its best whilst he was young and affably imbecilic. The star turn, however, comes from a brief but brilliant cameo from Chris Farley.

Tommy Boy

As for Farley, he was part of that new wave of SNL comedians turned movie stars and big things were expected of him, as they were from Sandler. Tommy Boy marked the first major lead role for Farley, finding himself in a comically mismatched double act with David Spade. Farley is all OTT explosions of manic and clumsy energy, clashing with the ruthlessly apathetic and dry character portrayed by Spade.

Though Tommy Boy lives on the chemistry of its two leads and the outrageous and ludicrous goofball comedy, it remains as popular and well-loved because it’s undercut with just the right amount of heartfelt sincerity. Tommy might be a comical buffoon, but he’s a good guy, and you’ll want him to win the day and save his family business.

Friday

Ice Cube has just unleashed upon the world a version of War of the Worlds that got even worse reviews than the version I co-wrote, called War of the Worlds: The Attack (it’s quite fun, I promise). 30 years ago, however, Cube showed himself as surprisingly adept at screen comedy, with the cult classic, Friday. He and Chris Tucker play a pair of slackers, in need of quick cash to avoid being killed by a fearsome gang leader (played brilliantly by the late, great Tiny Lister).

Tucker and Cube bounce off each other perfectly, and the film stepped ahead of many rival black-led comedies of the time thanks to great performances and the rising comical mishaps. It’s fair to say that the inimitable late John Witherspoon steals every scene he’s in, to the point I still have to watch his Friday highlight reels on YouTube.

Mallrats

After the success of Clerks, Kevin Smith was given just a little bit more money to play with and shot in colour, to give us Mallrats. Greeted by solid if unspectacular reviews, it didn’t feel like the out-of-left-field indie dong slap to the forehead that Clerks was, but that was never the goal.

In time, its irreverent slice of life charm has seen its legacy grow and is often cited as a favourite among Smith fans. Part of the Jay and Silent Bob universe, it feels as if it slots in and pairs well with the others, while retaining its own unique charms. The cast of (then) rising stars is in good form. Where it really found its lasting appeal for many, in how it stands up to multiple viewings. It’s pure comfort movie fare. Like the rest of Smith’s finer work.

Welcome to the Dollhouse

Todd Solondz’s film seems to have remained somewhat undervalued and underseen. With quirky oddball characters, a nerdy protagonist and a distinct style, it pairs very well with 2004’s Napoleon Dynamite.

Welcome to the Dollhouse’s style, pacing, and humour are an acquired taste (like Napoleon Dynamite in fairness), but if you vibe with it, there’s plenty to enjoy. The sheer affable awkwardness of Heather Matarazzo as Dawn, in this coming-of-age comedy, really makes this a joy. A perfect outsider comedy that captures its time and place so well.

Clueless

Perhaps more than any other film of 1995, Clueless really seemed to capture the zeitgeist. It didn’t so much brilliantly encapsulate that era as it did the overarching media representation of it. It was broad, loaded with caricatures of archetypal high-school cliques, not least with Alicia Silverstone’s protagonist, Cher. She’s the perfect amalgamation of every rich high school fashionista/sociolite you’ve ever seen in 80s and early 90s film and TV.

Clueless is filled to the brim with colourful characters, played to pitch perfection by the cast (including Paul Rudd, Stacy Dash and the wonderful Brittany Murphy). Spawning a TV spinoff, a musical and long long-held desire for a sequel, Clueless has aged very well, and its bright, nostalgic designs from sets to costumes, to bold performances, will appeal to new fans.

Bad Boys

Will Smith may have imploded his career with slaps, baffling lack of self-awareness and regrettable songs about how much he likes girls, but back in 1995, he was the biggest thing on TV, stepping into the big screen arena with Bad Boys. Likewise, Martin Lawrence was making the same jump, and we were about to discover what ‘Bayhem’ was.

Yes, 1995, I was 14 and upon watching Bad Boys (at the perfect mental age to appreciate it), I thought it was the greatest thing since someone decided bread should come sliced. In hindsight, the film is often infantile and ruthlessly simplistic, but it’s still masses of fun. Smith and Lawrence trade fast talking jabs relentlessly, and Bay cranks every stylistic choice up to 10 (he’d later move to 11 for the sequel and his 21st-century fare). It’s also loaded with quotable lines.

To Die For

Probably the most wryly satirical and black laced comedy of the year, To Die For was a real standout role for Nicole Kidman, courtesy of Gus Van Sant. From child actor to the starlet, almost unshakably known as a go-to love interest or just Tom Cruise’s wife, she showed a whole new fide with this pitch dark comedy as a weather girl plotting to murder her husband to further her career.

This film feels like it’s perennially viewed as an underrated gem you haven’t seen. Adorning many 90s-themed lists, focused on overlooked movies. It really does deserve more appreciation, and it remains one of Kidman’s best roles and performances. She was nominated for a Bafta and Golden Globe no less, and it was instrumental in her shift up to the top of the A list. 

Toy Story

How on Earth is Toy Story 30 years old? To make matters worse, having been years in the making, Woody and Buzz are even older than that. Never mind, because the legacy this film has is undeniable. It was the film upon which one of the great animation studios was built. Pixar, from here on and pretty consistently to this day, pumped out hit after hit and with rarely a misstep out of Five Star City.

Though we’ve had more elaborate and technologically advanced adventures of Woody and the gang since, the original film is still an unbridled joy for babies dazzled by the colour, right up to centenarians (dazzled by the colour).

Kicking and Screaming

It doesn’t feel like it, but Noah Baumbach has been firing out indie hits for 30 years, and it all began with Kicking and Screaming, not to be confused with the dire little league soccer comedy starring Will Ferrell.

Baumbach’s film showed a director learning the ropes but laying the foundations for a skilled blend of observational and hip ensemble comedy. Well-defined characters, thrust into adulthood and all the realities that entail, and their diverting pathways. It’s well cast with Eric Stoltz, somewhat seasoned by that point, and provided a good platform for Parker Posey to cultivate her on-screen persona. In fact, it was a great year for her, with Party Girl also coming out.

What’s your favourite comedy films from 1995? Let us know on our social channels @FlickeringMyth…

Tom Jolliffe

 

Filed Under: Articles and Opinions, Featured, Movies, Tom Jolliffe, Top Stories Tagged With: Bad Boys, Billy Madison, Clueless, Friday, Kicking and Screaming, Mallrats, To Die For, Tommy Boy, Toy Story, Welcome to the Dollhouse

About Tom Jolliffe

Tom Jolliffe is an award-winning screenwriter, film journalist and passionate cinephile. He has written a number of feature films including 'Renegades' (Danny Trejo, Lee Majors), 'Cinderella's Revenge' (Natasha Henstridge) and 'War of the Worlds: The Attack' (Vincent Regan). He also wrote and produced the upcoming gothic horror film 'The Baby in the Basket'.

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