219 Of Probably The Funniest 90s Movies

If there ever was a Christmas staple movie, Home Alone is it. Call it distasteful for adult bashing or stretched-thin; Home Alone is a truly iconic film of the ‘90s. To us die-hard fans, the gags are hilarious, the premise is unexpected (how is it possible to forget your own child?), and Macaulay Culkin is adorable beyond words.

There are very few actors as widely beloved as the late Robin Williams. Every movie he starred in warmed audiences' hearts and made them laugh, creating a wholesome movie-watching experience. Such is the case with Mrs. Doubtfire too, a goofy, lighthearted movie that, in the end, touches you profoundly. And, you might not know this, but a sequel to Mrs. Doubtfire was under work. Sadly, the idea was dropped right after the untimely death of everyone's favorite Williams.

Name at least one movie starring Marisa Tomei that's not funny or iconic. Or both. Anyway, we always love ourselves a sharp courtroom comedy, and besides being genuinely amusing, My Cousin Vinny was also lauded for being quite accurate on court procedures. A movie you can snort at and learn something valuable? Sign us up!

What's a sports comedy without broken bones, noses, and bruises during filming? Well, even though you couldn't tell that by watching the glorious all-girls baseball team (including a performance from Madonna!) on screen, but the making of A League Of Their Own did involve plenty of physical sacrifices from the cast. However, it isn't the thing that made this movie an iconic one. Instead, a thoroughly charming cast, non-soppy sentimentality, and lightheartedness are why this movie is still beloved even decades after its release.

Now, this is an iconic movie one might actually call time-defying (get it?). This movie is so impactful that even its name, Groundhog Day, became a widely-used phrase to reference a repetitive and monotonous situation. Groundhog Day's innovative use of the time loop made it popular with general audiences and was since repeated in several movies, TV shows, and video games. And though a direct sequel was quickly ruled out upon the original film's release, you can always relive Groundhog Day by watching a musical by the same name.

Men In Black, an adaptation of a comic book of the same name by Lowell Cunningham and Sandy Carruthers, was a bonafide blockbuster hit. Thanks to its original story, charismatic performances, and tasteful jokes, Men In Black secured itself three sequels, animated series adaptation, and spawned six video games.

As stated by the Friday director F. Gary Gray, working with Ice Cube in a comedy "scared the sh*t out of me." Yet we say it was funny as hell! Throw the "toughest man in America" into comedic situations on a buddy stoner film, and it is instantaneously hilarious. So if you're a fan of hood comedies, give this 1995 movie a look-see.

A simple premise doesn't always mean a simplistic movie. And though the main idea of a lawyer that's forced to tell nothing but the truth might seem like an incomplex one, the movie Liar Liar comes out as nothing but. With another stellar Carrey performance, this comedy gained favorable acclaim from audiences and cemented Carrey's comedian career.

Though a more 'serious' movie than others on our list, Big Lebowski by the Coen brothers has gained a cult-like following and even inspired a whole new philosophy called Dudeism. Peppered with hilarious and memorable performances from supporting actors (Turturro's Jesus is by far one of the greatest supporting characters ever), The Big Lebowski is a real adventure to watch. And if you haven't already, we strongly recommend it!

I won't even start counting the memes existing purely because of this hilarious 1994 movie. Yet, the most crucial point is proven once again - everything Jim Carrey stars in turns right into comedy gold. And who else, if not mister Carrey, would've made a bottlenose dolphin rescue such an uproarious affair.

A coming-of-age sports comedy that's so nostalgic it'll make you cry-laugh? Yes, it's The Sandlot in its full glory. As with most movies on our list, this comedy film found itself out of favor with the critics, but who are they to judge a comedy, right? And if one Sandlot just doesn't cut it for you - there are two sequels to this 1993 gem.

Starring Cameron Diaz, a legitimate It Girl of the era, There's Something About Mary was a wildly successful film. Listed in the American Film Institute's roster of 100 best comedies of all time, There's Something About Mary will always be funny due to its universal sense of humor, enjoyable performances, and lighthearted tone.

The aniseed of the movie industry, Adam Sandler is one of those guys whose movies and performances you love or loathe. But, no matter which side you are supporting on the aniseed debate, Happy Gilmore was a huge commercial success, gaining nominations for such sought-after awards as the Golden Raspberry Awards and Stinkers Bad Movie Awards! Not many movies in our list can beat that, for sure.

There are many cases when a book-based movie turns sour, but Clueless is a stellar example of how such a movie should look and feel, I daresay. Loosely based on Jane Austen's 1815 novel Emma, Clueless is considered to be one of the greatest teen movies ever made. The film's success propelled young Alicia Silverstone's career, had us all swooning for Paul Rudd, adopting the "As if!" and wishing for the dazzling outfits from Cher's and Dionne's closets.

Relentlessly stupid yet highly entertaining, Dumb and Dumber is truly an iconic comedy of the era. If not for the glorious partnership of everyone's beloved actors - Jim Carrey and Jeff Daniels - we're sure this buddy comedy film wouldn't have been as successful in the box office as it was upon its release.

Born out of a Saturday Night Live sketch, Wayne's World was the highest-grossing of 11 movies spawned from SNL. With a feature film debut performance from Mike Myers and such supporting cast as Dana Carvey, Rob Lowe, and Lara Flynn Boyle, Wayne's World was acclaimed critically and enjoyed great success among audiences. Filled with memorable catchphrases and original jokes, Wayne's World cemented itself as one of the best comedy movies of the ‘90s.

Though met with very lukewarm reviews, Tommy Boy has gained itself a spot on the cult movies list. Definitely not because of its predictability or jokes you've probably heard too many times, but because of the superb and loveable performances of Saturday Night Live colleagues David Spade and Chris Farley. So, if you're looking for a movie that'll surely induce a real-life ROFL, try Tommy Boy.

A commercial flop upon its release, Office Space later did so well with selling on home video and DVDs that it gained a cult-like following just a couple of years later. Several elements of the film are still reused as memes to this day - remember the one about working on Saturday? Curiously enough, a red Swingline stapler became a staple of the movie, and the manufacturers started offering such a non-existent-before stapler for purchase.

Though it might seem like an unlikely contender, we think Toy Story is absolutely worthy of being on our list of the best ‘90s comedies. Not only is it one of the most impactful animated movies, but it's also probably the only film with a cast member that went on a real space mission. Well, okay, not really a cast member, but a figurine of Buzz Lightyear taken on a Space Shuttle mission STS-124 in 2008 that was used for experiments in zero-g. Still quite an impressive achievement, I might say!

There's nothing better than a light-hearted, psychedelic parody of something as serious as the James Bond franchise. And Austin Power's frontman Mike Myers delivered it! A goofy spy, Bondesque gags, flocks of beautiful ladies clad in skimpy ‘60s attire, and iconic one-liners - everything you could've wished for in a comedy is here!

Surprisingly romantic, sweet, and beguiling, The Wedding Singer is consistently named one of the best Adam Sandler comedies. And you know what, we might just agree - everything's better with a bit of romance and an awesome soundtrack in it. It's also one of the few movies on our list that got a Broadway remake, and though it wasn't a massive success, The Wedding Singer musical has become popular with community theaters and high schools.

Five high school guys on a deflowering quest can only mean lots of embarrassment, hilarity, mishaps, and raunchy jokes. And if that's what you're looking for in a comedy, American Pie is a bullseye shot. This teenage drama-comedy-romp was so hugely successful that it spawned three direct sequels and five spin-off movies.

"Sssomebody stop me!" before I run and get myself a Milo from a dog shelter and try to mimic all the legendary scenes from The Mask. Loosely based on the comics by the same name, The Mask stars comedy icon Jim Carrey with a debuting Cameron Diaz by his side. Call it either fantastic or bombastic; this movie made us hee-haw throughout its whole 101 minutes run time and left us wishing for more of The Mask's shenanigans.

Ah, Adam Sandler and his never-ending portrayals of somewhat mentally challenged personas. So here's one more to add to this list - The Waterboy. And as with basically all the other Sandler movies from the era, this one was also nominated for Golden Raspberries and Stinkers Bad Movies. Still, to us, it encapsulates the naivete and simple way of living of the ‘90s better than anything.

A dark comedy starring Bill Murray can only mean success in our book. What About Bob? follows a relationship (of sorts) between an irritating patient and his psychotherapist. With such a premise, jokes can only get dark and the situations amusing. Interestingly enough, it might have been Woody Allen in the role of Dr. Leo Marvin and in the director's chair. However, he refused as he always worked on projects generated by himself.

Still not had enough of Adam Sandler? No probs, here's another movie of his, portraying a dimwitted adult as per usual! However, if you watch this movie keeping in mind that Sandler's persona is meant to be an irritating one, the laughs will definitely come, as some of the sequences in this movie are beyond hilarious.

A sequel to the 1995 Toy Story, it opened to wild box office success and just as its predecessor did, it gained a rare 100% rating on the website Rotten Tomatoes. But, if not for Galyn Susman, Toy Story 2 might've perished without us ever seeing it. See, in 1998, two years into making this animated film, one of the animators accidentally deleted all the material created up to date. But thanks to Galyn, who was working from home while taking care of her newborn baby, backup files were kept, and the production moved on.

There aren't many romantic comedies on our list, but it wouldn't be complete without Pretty Woman. Though it is filled with slick humor and charisma supplied by Julia Roberts and Richard Gere, the critics weren't too enthralled about Pretty Woman's premise, and the reviews were quite average. Average or not, the movie resonated with audiences and saw the highest ticket sales for a romantic comedy ever.

Another Golden Razzies and Stinkers award nominee by Adam Sandler on our list might not even come as a surprise anymore. What's surprising, though, is that it was the seventh highest-grossing movie of the year it was released and Sandler's biggest earner up until Hotel Transylvania 2. And though critics once again bashed Big Daddy, the film has an unlikely fan - director Paul Thomas Anderson (Boogie Night, There Will Be Blood) named it among his all-time favorite movies.

A second installment in the Austin Powers movie series, The Spy Who Shagged Me, was an instant box office hit. Filled with theme-appropriate jokes and spy-inspired gags, this movie was even more successful than its predecessor. And there's always a spot on our list for a special agent with horrible teeth and a great sense of humor!