

Who doesn’t enjoy a really great comedy that makes you laugh, lifts your spirits, and gives you a group of likable characters and memorable quotes for 90 minutes or so? The ’90s was packed with amazing comedies, with quite a few running under the radar, only to be discovered later on cable, rental, and streaming. Here are 50 titles that are, to varying degrees, overlooked or underrated. Some of these will be well-known, others fairly obscure and underrated. Hopefully you’ll find a few new titles to enjoy while remembering many more that delivered a great time back in the day.
And I’ll start this gigantic list off with…

Career Opportunities (1991): One of John Hughes’ last teen-centered projects, this one sticks the gorgeous Jennifer Connelly and some other dude in a Target overnight. It’s a fantasy in more than one way, but sadly not that well-known today.

Dirty Work (1998): Sadly undercut by a studio’s reluctance to give this an R rating and NBC’s vendetta against Norm Macdonald, Dirty Work bombed in theaters. Yet it became a legit cult comedy in ensuing years, and you can even find a “Dirtier Version” if you look hard enough.

Down Periscope (1996): Kelsey Grammer cuts loose as an unorthodox submarine commander with a ragtag crew of misfits… you know the drill! This is far better than what you might first assume and a great example of a solid ’90s comedy.

Mystery Men (1999): Made slightly before the huge superhero explosion of the 2000s, Mystery Men seems oddly ahead of its time in retrospect. A satire of superhero flicks with an amazing cast? Yes, please!

Heavyweights (1995): Judd Apatow and Ben Stiller collaborated on this subversive comedy about overweight kids stuck at a summer camp from hell. It’s got an edge that might surprise Disney viewers.

The Chase (1994): Charlie Sheen and Kirsty Swanson make sparks as an unlikely hostage duo racing for the Mexican border. It’s a really well-rounded movie that I find almost nobody remembers… but they should.

Dead Man on Campus (1998): How far would two college kids go to get an A? This slightly dark comedy sees how the effort to badger students into suicide for a good grade can backfire in unexpected ways. You’ll also never see Zack from Saved by the Bell in the same way again.

National Lampoon’s Senior Trip (1995): The National Lampoon brand actually produced something worthwhile this decade — a wacky senior class trip to Washingon with Tara Strong, Jeremy Renner, and Matt Frewer. It’s such a fun ride.

Overnight Delivery (1998): An ageless and manic Paul Rudd and angsty Reese Witherspoon go on a road trip that is the same plot of Road Trip (which this allegedly inspired). It’s a touch surreal and predictable in a romcom way, but that’s not a knock against it.

My Boyfriend’s Back (1993): Can you woo the girl of your dreams from beyond the grave? This imaginative and wildly funny movie says, “Absolutely you can! Just don’t fall apart doing it!”

Cabin Boy (1994): This surrealist voyage of a “fancy lad” on a boat will either be the best or worst thing you’ll see all year. It was a bomb that gradually, so gradually built up a fanatical following. Join this crew!

Noises Off! (1992): You don’t have to be a theater brat to appreciate the escalating antics of Christopher Reeve, Michael Caine, and company trying to get through a doomed play performance over three nights.

Kids in the Hall: Brain Candy (1996): The Canadian cult TV show became a cult movie in truth, and the world is richer for it… or it would be, if people actually watched this! It’s weird and demented, just like the sketch show was.

Can’t Hardly Wait (1998): The ultimate ’90s teen party flick, this movie has a great cast, kinetic energy, terrific music, and so many classic lines. Plus, Seth Green cosplaying a gangster is *chef’s kiss*.

Romy and Michele’s High School Reunion (1997): Perhaps the ultimate “dumb blonde” movie with stealthy smarts and some quotes I still use today. “Excuse me, I’ve got to go. I cut my foot earlier and my shoe is filling up with blood.”

Party Girl (1995): Parker Posey steps into a rare main role as a career party girl who trades her costumes in for a job as a librarian… and loves it. It’s not super-deep or angsty, but it is some of the most likable stuff Posey’s ever done.

Wrongfully Accused (1998): Leslie Nielsen was pumping out a lot of rotten spoofs by this point, but this one was actually worth seeing. It’s also got a strange fixation with Minnesota, because why not?

Crazy People (1990): This may be the only movie on this list my mom turned me on to, and that’s because she was in advertising for a few years there and thought that this lampooning of the advertising industry was amazing. It kind of is! Really funny ads and a group of mental patients proving that they can speak truth in a way that marketers can’t.

Trial and Error (1997): Made by the same guy who did My Cousin Vinny, this trial/romcom flick didn’t do nearly as well, even though it’s pretty funny in its own right. It’s about a lawyer whose actor friend ends up taking over for him at a backwater courthouse.

Major Payne (1995): There’s something deeply wrong and yet funny about an overly intense drill instructor turning that intensity on troubled kids. This was Damon Wayans Sr’s Billy Madison, if that makes ANY sense. Wouldn’t get made today, but you can watch it today.

Airheads (1994): Fraser, Buscemi, Sandler, Farley, McKean, and so many more crammed into this story of a radio station takeover by a dim-witted rock band. It’s perfect cinematic junk food for the soul.

The Brady Bunch Movie (1995): This may be the best and most clever ’90s adaptation of a TV show, and it’s all thanks to the idea of keeping the titular family stuck in a ’70s mindset while the culture has shifted around them. I love this and its sequel so much, and it never gets enough praise.

Almost Heroes (1998): Chris Farley’s last flick is a knee-slapping road trip through Americana — with Matthew Perry, no less. It’s very quotable and a worthy sendoff to a comedic legend.

Fatal Instinct (1993): Almost nobody remembers this Basic Instinct spoof, but it’s actually really good — even without Leslie Neilsen propping it up! And hey, isn’t that Shooter McGavin?

Mystery Science Theater 3000: The Movie (1996): This is a sleek starter package for the zany riffs of Tom Servo, Crow, and Mike. As a plus, we get a pretty fine scifi B-movie in the background!

The Ref (1994): Looking for a Christmas comedy with a bite? Denis Leary crushes it as a robber who takes a bickering family hostage on Christmas Eve, only to help them sort out their problems.

Night at the Roxbury (1998): The old school clubbing vibes are strong with this SNL skit-turned-flick. Chris Kattan and Will Ferrell are having a great time in this, and it shows.

Fierce Creatures (1997): I actually prefer this reunion of the Fish Called Wanda cast over their previous effort, as the foursome grapple with a struggling zoo that labels its adorable creatures as “fierce” to draw in crowds.

Empire Records (1995): I consider this to be the ultimate Gen X movie, tossing the viewer into a single day at the most unhinged record store on the east coast. Romance, music, concerts, pop stars, art, shoplifting, brownies, and far too many one-liners ensue.

BASEketball (1998): I consider this film the best that the South Park duo’s ever done. It’s edgy, slightly gross, and bonkers, all wrapped around an imaginary sport.

Stay Tuned (1992): Satan throws a bickering couple into an ever-changing TV wasteland of (now-very-dated) parodies, and it’s unlike anything else you’ll see that decade.

The Truth About Cats and Dogs (1996): This feels like a romcom for those of us who have no chance and no hope. Loads of witty exchanges and some very cute people (and pets!) fill in the runtime quite nicely.

The Castle (1997): An airport expansion can’t get in the way of this overly upbeat Australian family who fights tooth and nail to keep their home. This feel-good flick is a national treasure down under, and you owe yourself to see it.

Half-Baked (1998): Stoner comedies continued to be pretty popular in their own way this decade, and Dave Chapelle’s effortless charm carries this gonzo story through to the end credits.

PCU (1994): An amazingly prescient comedy about political correctness run amok on college campuses, PCU is wall-to-wall quotes, music, likable characters, and a pretty great message.

So I Married An Axe Murderer (1993): This feels like the only real solo Mike Meyers movie that’s not hanging on an IP of sorts — and it’s one of my all-time favorites. Great soundtrack, great supporting cast, and two roles by Meyers himself.

Don’t Tell Mom The Babysitter’s Dead (1991): Probably the most implausible premise ever, but who cares? It’s a wild journey of watching spoiled kids grow up in a hurry and finding that adulthood isn’t always the power trip they imagined. Loved the soundtrack, too.

Quick Change (1990): Bill Murray, Geena Davis, and Randy Quaid have a hoot as a trio of bank robbers who can’t seem to escape the town that they robbed. Any time that Bill Murray is given leeway to be sarcastic is going to be a good time, and this is definitely a good time.

Vegas Vacation (1997): Critics and the public dismissed this fourth Vacation entry, but it’s actually incredibly amusing. Cousin Eddie comes back, and Ethan Embry has a blast as “Papa Gorgio from Yuma.”

Loaded Weapon 1 (1993): If you know, you know — and fans of this spoof KNOW. You’ve got Emilio Estevez winding down his career while Samuel L Jackson is revving his up, and Tim Curry is right there in the middle.

Black Sheep (1996): The “other” Chris Farley/David Space collab, Black Sheep never gets brought up even though it’s actually pretty darn funny. Plus, these two actors have great chemistry together… I wish we got more.

Captain Ron (1992): Kurt Russell is a free-spirit captain who’s hired to take a family on the craziest Caribbean voyage of their lives. Everyone here looks like they’re having a blast.

Bill and Ted’s Bogus Journey (1991): Not quite the instant classic as the first film, Bogus Journey’s really grown on me as a trip through life, death, and the afterlife — with very early ’90s fashion. William Sadler rocks in this as the Grim Reaper himself.

Ski School (1991): A goofy ’80s-style throwback to non-conformists vs. snobs, this time on the powdery slopes. It was a laugh riot from start to finish — and the sequel ain’t that bad, either.

Son in Law (1993): Pauly Shore’s finest moment is a pretty great college flick, romcom, and fish-out-of-water tale all in one! Keep your eye open for a quick Encino Man cameo, too.

The Cutting Edge (1992): Toepick! Maybe my favorite romcom from the ’90s (and then again, maybe not), this love-hate relationship sports flick has two heated snarkers going at each other while the sparks fly.

The Man Who Knew Too Little (1997): Bill Murray gave us a spiritual successor to What About Bob? with this story of an American who becomes an inadvertent British spy thanks to an interactive theater event. It’s prime Murray.

Encino Man (1992): I am a massive fan of this zany caveman-out-of-time tale. Everything, from Brendan Fraser’s physical performance to the soundtrack to the early ’90s teen vibes, makes for great memories.

Hudson Hawk (1991): An absolutely surrealist comedy with a big budget, Hudson Hawk confused everyone expecting Die Hard with a Burglar Mask. It’s so weird and goofy, and I love it to pieces. It’s also the movie that kicked off Mutant Reviewers!

The Wrong Guy (1997): Definitely the funniest movie you’ve never seen, this one stars Dave Foley as a dope who thinks he’s on the run for a murder he didn’t commit, but nobody’s actually chasing him. Trust me, you got to see this one.