Though I grew up in the 80s, and my first movie memories are from that decade it wasn’t until the 90s that I started to earn my own money, and attend the movies on a regular basis. It also wasn’t until that decade that I was finally old enough to attend movies that were rated R, and once I crossed that barrier movie viewing got a whole lot more interesting. Many of the movies of this list of the top 40 best comedy movies of the 90s earned that restricted rating, and though Bill Cosby might disagree those movies in many cases seem to elicit more laughter than their more family-friendly brethren.
That’s not to say there are a fair number of family friendly movies on the list. A film doesn’t have to be filled with profanity or crude sex jokes to get laughs. However, if it doesn’t rely on those cheap and easy laughs the writing has to be top notch to get increasingly desensitized audiences laughing.
When I made this list I tried to strike a balance of raunchy comedy and good clean laughs. Please feel free to let loose in comments and let me know if I’ve succeeded. Here are my picks for the funniest movies of the 90s.
40 – Four Weddings and a Funeral – Though romantic comedies are far from my favorite brand of movie I have to admit that as far as “chick flicks” go this Hugh Grant / Andie MacDowell collaboration isn’t bad. With witty dialogue throughout and some dark humor this film manages to keep guys and girls alike entertained throughout.
39 – Rush Hour – Though Jackie Chan’s best comedy work came in the western movie Shanghai Noon, co-starring Owen Wilson, he also had some pretty good chemistry with the abrasive comedian Chris Tucker. A hybrid action/comedy film Rush Hour has something to satisfy both types of movie fans. Rush Hour also turned out to be a great commercial success, spawning two sequels, and turning Jackie Chan into an international comedy star.
38 – Chasing Amy – Director Kevin Smith burst on the scene back in 1994 with the low budget, black and white cult comedy classic Clerks. Smith quickly proved he was no one hit wonder, reeling off several more comedies in the 90s. As with all Kevin Smith movies the dialogue is absolutely hilarious, and though this movie might seem a bit mainstream compared to Smith’s other works it is still very far from the usual Hollywood romantic comedy.
37 – Billy Madison – As soon as you see Adam Sandler’s name attached to a 90s comedy movie you can be pretty sure you’re probably not going to be very intellectually stimulated. However, the beauty of a comedy movie is that it doesn’t have to make you think; it just needs to make you laugh. Sure Billy Madison has more than its fair share of dumb humor, but you can’t help but laugh at the goofball humor and the ludicrous plot. Not Sandler’s best work, but good enough to squeak onto this list.
36 – Liar Liar – There was arguably no bigger comedy star in the 90s than Canadian funnyman Jim Carrey. Though his recent work has been more subdued, and he has even taken some dramatic turns, back in the prime of his popularity he was an over-the-top outrageous ham who could get even the most jaded viewer to burst out in laughter. In this film Carrey is perfectly cast as a lawyer who is cursed (or blessed) by the sudden inability to tell a lie. Carrey finds himself spilling his guts in all sorts of awkward situations (one particularly amusing scene takes place in an elevator). Not only is it funny, but Liar Liar manages to be a little touching as well, and even manages to slip a life lesson in there somewhere. One of Carrey’s most underrated films in my opinion.
35 – The Nutty Professor – I’m normally not a fan of remakes of classic movies, but this one was so different from the original as to seem like a completely different movies. One of the biggest comedy stars of the 80s Eddie Murphy had been in a career slump until he landed this role as Sherman Klump (and about 10 other people). Again, not much intellectual comedy here, but plenty of cheap laughs to be had.
34 – Romy and Michelle’s High School Reunion – Like blonde jokes? Love the 80s? ThenRomy and Michelle’s High School Reunion should be right up your alley. It is a bit of a talent mismatch with Oscar winner Mia Sorvino pairing up with Lisa Kudrow (Phoebe from Friends) in the lead roles. Still, the two manage to generate pretty good chemistry together.
33 – The Birdcage – This is a film that always seems to get overlooked on these lists, so I wanted to give it the kudos it deserves. Robin Williams and Nathan Lane star, so you know right off the bat the comedy will be outrageous and flamboyant. As Armand (gay cabaret owner) and Albert (his drag queen lover) they certainly deliver on both parts. Gene Hackman is equally good as a straight-laced senator whose daughter is engaged to Armand and Albert’s son. At their son’s request Albert and Armand must put up a front as a normal, conservative family. Not an easy task to say the least.
32 – Men in Black – This is another movie I never see on lists of best comedy movies. Whether it is simply overlooked or the authors simply don’t find it funny I don’t know. Personally I think it is a fantastic blend of sci-fi and comedy. Will Smith is great in his role as N.Y.P.D. police officer turned interstellar agent Jay, but it is straight man Tommy Lee Jones as Kay who really steals the show. This one is definitely worth another viewing if you haven’t seen it in the last decade or so.
31 – City Slickers – Any guys out there currently in the midst of a midlife crisis? Then this is the movie for you. Billy Crystal, Daniel Stern, and Bruno Kirby all star as three city boys who decide to shake up life a little by taking part in a real life cattle drive. Crystal’s sarcastic character Mitch Robbins immediately finds an enemy in ranch hand Curly Washburn, played to perfection by Jack Palance, and the funniest parts of the movie revolve around the conflict between the two.
30 – Hot Shots! – This isn’t a film that will appeal to everyone reading this list. However, if you like parody films like Airplane! and The Naked Gun then you will no doubt appreciate this spoof of Tom Cruise’s 80s hit film Top Gun. Charlie Sheen shows he had talent for comedy long before his hit sitcom Two and a Half Men, starring in the lead role as Topper Harley, a pilot with a haunted past who must get back into the cockpit to save the day. Sheen’s Two and a Half Men co-star Jon Cryer also appears in the film, along with Cary Elwes, Valeria Golino, and the always brilliant Lloyd Bridges, who steals many scenes in the film.
29 – Tommy Boy – Saturday night live alum David Spade and the late Chris Farley team up in this side-splitting comedy about a goof-off son who must grow up in a hurry in order to save the family auto business. Farley once again delivers his signature boisterous but charming, physical brand of comedy, and Spade as always shows his talent for delivering sarcastic quips. Though most of Farley’s film career was pretty forgettable compared to his SNL skits, this film is definitely the exception.
28 – My Cousin Vinny – Not many of the films on this list of the funniest movies of the 90s can boast an Oscar nomination, let alone a win, but this 1992 movie bucks that trend. Marissa Tomei, who was recently so good in The Wrestler landed a Best Supporting Actress statue for her work on the film. Joe Pesci is hilarious as Vinny, an inexperienced lawyer who comes to the rescue of a pair of his family members who’ve been mistakenly accused of murder and now face the death penalty. Vinny’s methods are unorthodox to say the least, but he gets the job done.
27 – Jerry Maguire – Though the signature line from this movie has been absolutely beaten to death in popular culture in the intervening years since its release it is hard to deny the popularity and the impact of this film when it was first released. This one, like My Cousin Vinny also landed an Oscar, with Cuba Gooding Jr. getting the nod as Best Supporting Actor. Tom Cruise, Renee Zellweger and Jay Mohr also deliver great performances, though much of Maguire’s over-the-top behavior in hindsight seems annoyingly close to his recent real life antics.
26 – Uncle Buck – It was a sad day for fans of comedy movies when legendary Canadian comic John Candy passed away. However, before Candy’s untimely death he created a number of comedy classics including Planes, Trains and Automobiles, The Great Outdoors, Home Alone and Spaceballs. However, his best character might have been the lazy but loveable Uncle Buck, who must grow up in a hurry when he is left in charge of his niece and nephew. Hilarious and touching at the same time, this movie is a classic that can be enjoyed by the whole family.
25 – The Cable Guy – No surprise to see Jim Carrey again on the list. Once again he is hilariously over the top as a cable repairman who terrorizes his new neighbor (Matthew Broderick) after his overtures of friendship are rejected. Anyone who has ever been to Medieval Times will find one scene in this film particularly amusing.
24 – What About Bob? – Though his most legendary films like Caddyshack, Ghost Busters andStripes were all from the 80s, funny man Bill Murray continued to make people laugh in the 90s. One of his best films of that decade was What About Bob? where Murray annoys therapist Dr. Leo Marvin (Richard Dreyfuss) nearly to death as he strives to deal with his OCD.
23 – Dazed and Confused – Though on the surface this 70s high school movie might not seem like a pure comedy there is plenty of underlying humor that will have you cracking up. Matthew McConaughey is absolutely brilliant in the role he was born to play – David Wooderson – a 20-something city worker who keeps reliving his glory days by hanging out with high school seniors. This is one of those films chock full of classic quotes, and is a great movie to watch while enjoying a few beers (or other things) with buddies.
22 – South Park: Bigger, Longer and Uncut – Though The Simpsons pushed the boundaries of good taste for television (in those days), Trey Parker and Matt Stone’s South Park took it to the next level, offending just about every demographic possible with their brand of crude humor. However, it wasn’t until they shed the restraints of television and hit the big screen that we saw just how demented the minds of these two comic geniuses really were. Appallingly crude, this is a movie that certainly won’t appeal to everyone, but if you aren’t easily offended and love shock humor then this animated classic will be right up your alley.
21 – Rushmore – About as polar opposite as you can get from South Park is the clever, intelligent comedy Rushmore. Jason Schwartzman, who is brilliant as Jonathan Ames on the HBO series Bored to Death showed his comedic talent right off the bat with his big screen debut in this film about a student with a strange addiction to his prep school . Bill Murray co-stars as his nemesis in love and war, Herman Blume. If you haven’t seen this film, or it’s been so long you don’t remember, definitely give it a rent and reacquaint yourself.
20 – Naked Gun 2 ½ – Leslie Nielsen is absolutely hilarious as Lt. Frank Drebin in this full length spin-off of the short-lived TV show Police Squad!. The film uses the same type of parody humor asAirplane! and Hot Shots so if you liked those films this one will be right up your alley. The cast is definitely unusual with Priscilla Presley, Ricardo Montalban and even OJ Simpson all surprising funny in supporting roles.
19 – The Wedding Singer – Though I’ll admit that romantic comedies aren’t exactly my thing, this film is definitely an exception to the rule. Adam Sandler and Drew Barrymore co-star, and many of Sandler’s usual cohorts make appearances in the film. Set in the 80s the movie will bring back some amusing memories for those who grew up in that decade.
18 – A Night at the Roxbury – The inclusion of this film on the list will definitely produce some cries of outrage. Yes, the acting by former SNL stars Will Ferrell and Chris Kattan is pretty awful, but there is something just so lovable about the Butabi brothers, who just want to get into the hippest club in town and rub shoulders with Richard Grieco. Critics will argue this one would have been better left as an SNL skit, but I for one (and I may be in the minority) think there is enough goodness here to warrant the full length feature film they made.
17 – Nothing to Lose – This one probably flew under a lot of people’s radar, and that makes it one of the most underrated comedies of the past couple of decades. Martin Lawrence gives one of his best performances, and co-star Tim Robbins shows an amazing talent for comedy. The pair of “desperate” men share great on screen chemistry, and there is plenty of witty banter between the two. I dare you not to laugh at the “feet on fire spider scene” or the “security guard dance scene”.
16 – Wayne’s World – Another SNL skit that became a feature film, this movie helped launch Canadian comedian Mike Myers into international superstardom. Dana Carvey co-stars in this film about a pair of long hair wannabe rockers who shoot to fame with a local cable access show in their basement. Though the humor is pretty dated now, you’ll still find yourself laughing out loud at points, and you definitely won’t be able to resist banging your head along with the boys to Queen’s Bohemian Rhapsody.
15 – Home Alone – Though at the tender age of 10 Macaulay Culkin already had a few feature films under his belt, including Uncle Buck is was this 1990 classic that really launched the child star’s career. Culkin’s character Kevin McCallister is forced to fend for himself after his stressed out family forgets him at home when they take off to France for a Christmas vacation. To make matters more complicated Kevin must defend his home against two bumbling criminals, played by Joe Pesci and Daniel Stern, who try to loot the house in the family’s absence.
14 – Mallrats – In my opinion this is Kevin Smith’s most underrated movie, and anyone who hung around the mall as a teenager will find plenty to identify with here. Jason Lee is classic as Brodie, a Sega-hockey-playing, comic-book-obsessed slacker who just got dumped by his girlfriend. He, along with buddy TS, also recently single, hit up the local mall and the adventure begins. If you are a fan of films like Clerks and Dogma you’ll definitely like this film.
13 – Groundhog Day – Bill Murray is spectacular (as usual) in this film about an arrogant weatherman who is forced to relive the same day (Groundhog Day) over and over again. Of course at the end Murray’s character predictably learns a life lesson and changes his ways, but before the typical Hollywood ending kicks in there are plenty of laughs to be had along the way.
12 – Office Space – This 1999 laugh-fest would find a high spot on a list of the biggest cult movies of all time. Peter Gibbons, a disgruntled worker suddenly finds he has ultimate freedom when a hypnotist puts him in a state of perpetual bliss, and then dies before lifting the suggestion. As a result he has no emotional qualms about hatching a plot to use a computer virus to bilk his company, after two of his best friends get their notice at work. Gary Cole co-stars as one of the truly iconic characters in comedy movie history – Bill Lumbergh – and his classic quotes live on to this day in popular culture.
11 – Waiting for Guffman – I really wanted to put the movie Best in Show on this list, but it actually came out in the early 2000s, and thus was ineligible. However, this Christopher Guest-directed film is very similar in tone, and is every bit as funny. This time instead of poking fun at the dog show world Guest takes jabs at the world of community theater actors and directors. It is a film that won’t appeal to all tastes, but if you get the humor you’ll definitely be laughing consistently throughout.
10 – Happy Gilmore – Adam Sandler gets the dubious honor of ushering us into the top 10 funniest movies of the 90s. As good as he was in The Wedding Singer Sandler’s best role has to be as hockey player turned golfer, Happy Gilmore. Channeling his anger and his incredible power Gilmore becomes an instant sensation on the tour as he tries to earn enough to save his grandmother’s house. The film has a number of classic scenes including a fist fight between Happy and former Price is Righthost Bob Barker. As with most Sandler movies the acting is pretty iffy, but the physical comedy and the biting one-liners are gold.
9 – Austin Powers: International Man of Mystery – If Wayne’s World made him a star it is this spoof of Ian Fleming’s iconic James Bond character that really launched Mike Myers into the stratosphere as a Hollywood A-list actor. Myers is brilliant as both British superspy Austin Powers and as Powers’ nemesis, the diabolical Dr. Evil. This is another movie that has transcended the film medium and has become intertwined with pop culture, and quotes from the movie like “Yeah, baby, yeah!” and “Shall we shag now, or shall we shag later?” could be heard in conversations all over the world for years following the movie’s release.
8 – Dumb and Dumber – The title alone should tell you that this is certainly not intellectually stimulating comedy. However, to qualify for this list of the best comedy movies of the 90s a film only needs to do one thing: make the audience laugh, and this film delivers laughter in buckets. Jim Carrey is great as always as the moronic limo driver Lloyd Christmas, but Jeff Daniels also displays a surprising talent for comedy as his equally imbecilic friend Harry Dunne. The pair might not have a combined IQ of 100, but they use sheer determination to get the upper hand on the bad guys in this film. There are too many classic lines and scenes in this film to count, but the snowball fight scene alone is worth shelling out the money to add the DVD to your collection.
7 – American Pie – Though the original brilliance of this movie has been watered down by a large number of sequels, spin-offs and imitators when it first arrived in theaters in 1999 it became an instant comedy classic. I don’t know if I’ve laughed as hard or as often in a theater before or since. Yes, there is plenty of dumb, gross-out high school humor, but the situational comedy about a group of friends who make a pact to lose their virginity is fantastic. Seann William Scott delivers another comedy icon as the obnoxious, but very amusing, Steve Stifler. If you’ve avoided seeing this film because you’re tired of the cookie-cutter copycat films that have been churned out of Hollywood over the past decade, I advise you to reconsider. This movie will still make you laugh.
6 – Clerks – One of the most original films to ever come out of the comedy genre, Kevin Smith’sClerks is a low budget masterpiece. Filmed in black and white the film details the daily existence of two convenience store clerks – Dante and Randal. Though it might not sound like the fodder for great comedy it is the dialog that really makes this film stand out. The back and forth banter really rings true, and though the situational comedy might not be as plausible it is still a film that anyone who has worked in a similar setting can identify with.
5 – Ace Ventura: Pet Detective – Though he’d appeared in several feature films and had been making people laugh for years on the popular comedy television show In Living Color it was this 1994 film that turned Jim Carrey into a household name. The role of Ace Ventura was the perfect vehicle for a ham like Carrey and he showed off his incredible physical comedic talent as an animal investigator. He would use the success of the film to springboard into the lead roles in such films asThe Mask, Dumb & Dumber, The Truman Show and the Ace Ventura sequel When Nature Calls.
4 – Kingpin – The Farrelly brothers make another appearance in the top 10 with this classic bowling movie. When Roy Munson’s dreams of becoming a bowling star are abruptly “cut off” he is forced to live vicariously through a young Amish man to gain revenge on his nemesis Ernie McCracken (Bill Murray). Like most Farrelly brothers movies there are a couple moments in this film that will make you squirm, but if you can get through those you’ll be laughing the rest of the way.
3 – Swingers – Another cult classic this film stars a pair of young and up and coming comedy stars in Jon Favreau and Vince Vaughn. Vaughn’s character Trent becomes something of a Mr. Miyagi to Favreau’s Mike, showing him the ropes of the club scene. When it comes to classic comedy movie quotes this film stacks up against the best of them, and is a movie that should be in every self-respecting comedy movie fan’s DVD library.
2 – There’s Something About Mary – As you can tell, I am a fan of the Farrelly brothers. However, I don’t think personal bias weighed into the decision to have this movie at the number 2 spot on the list. Ben Stiller stars in the lead role as Ted, a man who has been obsessed with Mary (Cameron Diaz) ever since he missed out on the opportunity of a lifetime to take Mary to prom in high school (due to a very unusual and painful accident). However, he is not alone. Mary has a long list of suitors, including Matt Dillon’s Healy, Lee Evans’ Tucker, Chris Elliott’s Dom and Brett Favre’s Brett Favre. You won’t be able to resist laughing at this one at the same time as you are grossed out. Hair gel scene anyone?
1 – The Big Lebowski – Okay, so maybe personal bias can be blamed on my selection for the #1 spot on my list of the top 40 best comedy movies of the 90s. However, just because I have an unabashed love of this film doesn’t mean it shouldn’t qualify for top spot. The dialog between the Dude (Jeff Bridges), Walter (John Goodman), Donny (Steve Buscemi), Jesus Quintana (John Turturro), and the rest of the brilliant cast of actors is absolutely hilarious, and that more than anything is what makes this movie so funny. The plot may seem convoluted after the first viewing, but watch the film a couple more times and you will get it sorted out, and you will appreciate the brilliance of the Coen brothers. I can’t recommend this film highly enough. It is a cult classic that grows more popular with each passing year, and there is a good reason for that. It is, quite simply, one of the funniest movies ever made.