22 of the Most Hilarious Films of All Time

Movies are some of the best therapy humans can give themselves. Whether you want to laugh out your sorrows, indulge your mental health needs with a great rom-com, or delight in scaring your best friend with a killer horror flick, movies are a medium that unequivocally caters to everyone without bias. If you’re looking for the laugh of your life, that belly-busting guffaw that sticks with you forever, we’ve got some great movies up for grabs. So, pick one for your next movie night and work your ab muscles with laughter!

1. TOMMY BOY (1995)

Tommy Boy (1995)
Image Credit: Paramount Pictures.

Chris Farley and David Spade star in this non-stop comedy piece. Given to partying more than studying, Tommy Callahan is all about a good time. Richard Hayden is the no-nonsense babysitter who goes on the road with Tommy to try and save the family business. If you’re a fan of David Spade, you’ll love this laugh-filled offering that features the late Chris Farley in one of the most iconic roles of his unfortunately short life. Tommy Boy is a fantastic watch for anyone looking for non-stop laughs.

2. TRAINS, PLANES, AND AUTOMOBILES (1987)

Trains, Planes, and Automobiles (1987)
Image Credit: Paramount Pictures.

If you like to laugh, you can’t do much better than Planes, Trains, and Automobiles. I’ve seen this movie at least four times, and the laughter comes so quickly every single time. Featuring the legendary Steve Martin and the late John Candy, this movie is a feel-good flick perfect for holiday cheer or any time of the year laughs as Martin plays businessman Larry Page. Page is trying to make it home for Thanksgiving when he crosses paths with Del Griffith, a shower ring salesman with a heart of gold and a penchant for getting Page into mishap after mishap. You’ll laugh until your sides hurt and tears roll out of your eyes.

3. NIGHT AT THE ROXBURY (1998)

Night at the Roxbury (1998)
Image Credit: Paramount Pictures.

Based on a sketch from the ever-popular Saturday Night Live called “The Roxbury Guys,” Will Ferrell and Chris Kattan play oddball brothers Steve and Doug Butabi. By day, these two work for their father, delivering orders of artificial flowers to clients. By night, they frequent nightclubs to practice picking up women, which they fail miserably. Their dreams are to gain entry into Roxbury, a trendy downtown nightclub they are never allowed to enter, and to open up a lounge to rival the Roxbury.

4. MONTY PYTHON AND THE HOLY GRAIL (1975)

Monty Python and the Holy Grail (1975)
Image Credit: 20th Century Studios.

Easily one of the best and most well-known comedies ever made. On a severely low budget of around $410,000, which was crowdsourced before crowdfunding was a thing, Monty Python and The Holy Grail has risen to the height of the second-best comedy in British history, a fitting place for a film such as this.

5. LOCK, STOCK AND TWO SMOKING BARRELS (1998)

Lock, Stock and Two Smoking Barrels
Image Credit: Summit Entertainment.

Guy Ritchie directed this British black comedy about four friends who stink at being criminals and the series of “bad guys” they run into. When friends Eddie, Tom, Soap, and Bacon put together more than $125,000 to enter a high-stakes card game, they’re assured a win because Eddie is a master card shark. Unfortunately for him and his friends, however, their opponent, Harry “Hatchett” Longdale rigs his games so that he always comes out on top. As Eddie and his friends try to regain their financial loss, Eddie tasks Tom with disposing of a set of antique shotguns that came to them during their attempt to regain their loss and the only evidence left to tie them to the case of stolen money and drugs.

6. FANBOYS (2009)

Fanboys (2009)
Image Credit: The Weinstein Company.

If there was ever a movie about Star Wars that you had to see, even though it wasn’t an original Star Wars film, this is it. Fanboys is an epic comedy about four superfans who are running out of time. One of them is dying, quite literally, to see the screening of Star Wars: Episode 1 – The Phantom Menace. With a ton of cameo appearances from stars you’ll know, including William Shatner and Carrie Fisher, Fanboys remains a classic comedy, especially if you’re also a fanboy.

7. WHAT ABOUT BOB? (1991)

What About Bob (1991) - Bill Murray
Image Credit: Touchstone Pictures.

Bill Murray and Richard Dreyfus were a comedy match made in Heaven when they teamed up for What About Bob? Bob Wiley is an anxious individual who relies on his therapist, Dr. Leo Marvin, to reassure him constantly. When Dr. Marvin decides to go on vacation, Bob follows him, interjecting himself into Leo’s downtime. His laughable hijinks are too much for Leo to handle, especially as his family begins to accept Bob’s presence. Hilarity ensues as Leo becomes more and more aggravated by Bob’s constant neediness, mainly because his family finds Bob endearing. Despite some off-set rudeness on Murray’s part, both Drefus and Murray pulled off one of the best comedies of the early nineties.

8. NAKED GUN 33 1/3 (1994)

Naked Gun 33 13 (1994) - Leslie Nielsen
Image Credit: Paramount Pictures.

When it comes to comedy, there is nothing quite like a Leslie Nielsen comedy. Add in OJ Simpson, the late Anna Nicole Smith, and even Weird Al Yankovich, and you’ve got a recipe for disaster that will keep you laughing until your sides hurt. Nielsen, who starred in 100 movies and 1500 television episodes, including the Naked Gun series, was legally deaf and wore hearing aids most of his life. Even so, he was able to make a healthy success of his comedic acting career.

9. RAISING ARIZONA (1987)

Raising Arizona (1987) - Nicolas Cage, Holly Hunter, and T.J. Kuhn
Image Credit: 20th Century Studios.

Nicolas Cage and Holly Hunter star in this hilarious film about a subject that isn’t quite so funny. Infertility is no laughing matter, but Ethan and Joel Cohen turned the issue into comedic gold with Raising Arizona. When Edwina and H.I. McDunnough can’t have a baby, they decide that watching over one of Nathan Arizona’s five babies will do them just fine and create the family they’ve always wanted. Nathan Arizona Jr. is one of Arizona’s quintuplets. As the most famous furniture magnate in their small town, his family is well-known, and Ed figures they don’t need so many children anyway. However, once the little boy is in their care, the pair will run into several off-the-wall situations as they try to keep “Junior” safe. When Nathan Sr. offers a reward for his son’s safe return, everyone will be hunting Ed and H.I. to try and get their hands on the boy. John Goodman, William Forsythe, and Sam McMurray starred in this over-the-top, heartwarming, hilarity-inducing film.

10. HAROLD & KUMAR GO TO WHITE CASTLE (2004)

Harold & Kumar Go to White Castle (2004)
Image Credit: New Line Cinema.

When friends Harold and Kumar decide they’re hungry and take a trip to White Castle Burgers, they’ll encounter situations they never imagined. Side-splitting humor and, for some, a sense of deja vu will keep you entertained and laughing from start to finish. As these two friends try to survive a trip that is anything but the easy answer to their extreme case of the munchies, they’ll overcome a set of the most extreme obstacles to score burgers from White Castle.

11. 40 YEAR-OLD VIRGIN (2005)

40 Year-old Virgin (2005) - Steve Carell
Image Credit: Universal Pictures.

Steve Carrell, Seth Rogen, Paul Rudd, and Romany Malco star with Catherine Keener in this stupid-funny film about a shy guy who is so introverted that he’s a virgin at 40. Thanks to his colleagues, who are dead set on ending his celibacy, Andy gets all sorts of advice on how to go about wooing a woman. Fortunately for him, he could be better at taking direction. However, when he meets Trish, all bets are off, and the laughs keep coming. A

12. SUPER TROOPERS (2001)

Super Troopers (2001) - Jay Chandrasekhar, Steve Lemme, Paul Soter, and Erik Stolhanske
Image Credit: Fox Searchlight Pictures.

Buckle up for a laugh-out-loud patrol party. When four Vermont state troopers vie for the prestige of prominence with the local police department and enjoy razzing citizens who use their stretch of the highway, you’re only guaranteed non-stop laughs. While the humor here is purposefully mind-numbingly stupid, this is not a family movie night option if you have young children. Seventeen and up for this one, and if you’re in the mood to keep the comedy rolling, there is a sequel, Super Troopers 2.

13. LIAR LIAR (1997)

Liar Liar (1997) - Jim Carrey and Amanda Donohoe
Image Credit: Universal Pictures.

One of Jim Carey’s finest films is the 1997 comedy gem Liar Liar. When Fletcher Reede disappoints his son on his birthday, the little boy makes a bold and catastrophic wish, at least for his lawyer dad. Unable to tell a lie for 24 hours, Fletcher finds himself impossibly hindered by a big case he’s supposed to handle that afternoon. As his life starts to spiral out of control because he has to be brutally honest, the laughs that only Jim Carey can pull off ensue over and over again. In fine Carey fashion, you’ll want to watch this one on repeat.

14. NATIONAL LAMPOON’S ANIMAL HOUSE (1978)

National Lampoon's Animal House (1978) - John Belushi, Tom Hulce, and Stephen Furst
Image Credit: Universal Pictures.

Before anyone knew Jim Belushi, they knew his older brother John. Larger than life and gone far too soon, this actor had a way with slapstick comedy that was as natural as breathing. National Lampoon’s Animal House was just one example of John Belushi’s easy, laugh-inducing antics that made him a household name. The comedic legend, who burst onto the scene on Saturday Night Live, left us far too soon.

15. THE MONEY PIT (1986)

The Money Pit (1986) - Tom Hanks and Shelley Long
Image Credit: Universal Pictures.

While Tom Hanks went on to star in numerous roles, from serious drama to raucous comedy, The Money Pit is one movie that endeared him to fans before he got his star on the Walk of Fame. One of the moments that made this movie so special is Hanks’ characteristic laughter when their tub falls through the floor.

The Money Pit truly couldn’t be any more apt for those who’ve gone through the painful and sometimes costly expense of renovating a home, and yet seeing Anna and Walter go from happy homebuyers to miserable cohabitants is undoubtedly, as one respondent says, “one of the most underrated films of the 1980s.”

16. DIRTY ROTTEN SCOUNDRELS (1988)

Dirty Rotten Scoundrels (1988) - Steve Martin and Michael Caine
Image Credit: Orion Pictures.

Comedy is sure to ensue when you put Steve Martin, Michael Caine, and Glenne Headly together. Freddie Benson (Martin) is stepping on the toes of another con artist, (Caine), but for all their worldly knowledge, they don’t know everything, particularly about women. Still, the way they go about conning a young woman working together, even as they try to one-up one another, is all they need to keep you laughing until the very end. Remade from Bedtime Story (1964), which starred Marlon Brando, David Niven, and Shirley Jones, this version does justice to the story for the Gen X crowd and is one they can pleasantly show their older children for a night of fun and easy laughter.

17. BILLY MADISON (1995)

Billy Madison (1995) - Adam Sandler and Bridgette Wilson-Sampras
Image Credit: Universal Pictures.

As Adam Sandler’s first significant movie role, Billy Madison solidified his comedic ability, leaving Sandler open to more films like Happy Gilmore and The Wedding Singer. While some would argue that Sandler is the same “dim-witted” character in every role, The Cobbler showed depth and his ability to take on more serious roles. Four years later, Sandler starred in Uncut Gems, showing a maturing acting repertoire that has come with age.

18. WHITE CHICKS (2004)

White Chicks (2004) - Marlon Wayans and Shawn Wayans
Image Credit: Columbia Pictures.

Marlon and Shawn Wayans go savagely undercover to save their careers and the lives of two hotel heiresses, Brittany and Tiffany Wilson. Their antics are iconic comedy and brilliantly scripted after disguising themselves as the two young women. The idea that no one would see through their disguises is a bit of a stretch and only adds to the comedic value of this film. If you want to laugh aloud, you could do much worse than a trip with two White Chicks.

19. SINGING IN THE RAIN (1952)

Singing in the Rain (1952) - Gene Kelly, Debbie Reynolds, and Donald O'Connor
Image Credit: Loew’s Inc.

1952 was a fantastic year for cinema. Gene Kelly and Debbie Reynold starred in a beautiful, uplifting musical romantic comedy known as Singing in the Rain. Kelly portrays Don Lockwood, a silent film star, transitioning alongside his co-star Lina Lamont to “talkies.” Don, who has been trying to dissuade Lina from pursuing him, finds himself obsessed with Kathy Selden, a woman he met when he took refuge in her car while escaping a slew of fans. Gene Kelly’s performance in the film was one-of-a-kind.

20. BLACK SHEEP (1996)

Black Sheep (1996) - Chris Farley and David Spade
Image Credit: Paramount Pictures.

Comedic duo David Spade and Chris Farley are back in the usual fashion for Black Sheep, where Spade plays political aid Steve Dodds to gubernatorial candidate Al Donnelly. As an aid, Spade takes on the adventurous task of keeping tabs on Mike, Al’s younger and certainly dopier brother. Mike, who has a heart of gold, can’t seem to figure out how to do anything without screwing it up on a grand scale, and Steve’s only job is to keep Mike as far away from Al’s campaign as possible until after the election. While Farley wasn’t particularly fond of how Black Sheep turned out, we’re still fans of this outing.

21. AIRPLANE! (1980)

Airplane! (1980) - Leslie Nielsen and Lorna Patterson
Image Credit: Paramount Pictures.

Leslie Neilsen is at it again in Airplane! When a jetliner crew takes ill, Ted Striker, a capable pilot except for his fear of flying and subsequent drinking problem, is asked to step in and land the giant plane. Thanks to Dr. Rumack (Neilsen), Ted knows the crew and several passengers received rotten fish that caused them to have food poisoning. While Ted tries to land the plane, slapstick gags, and ever-quotable lines will bring you back again and again for the type of laughter that makes your sides hurt.

22. PINEAPPLE EXPRESS (2008)

Pineapple Express (2008) - James Franco, Seth Rogen, and Danny McBride
Image Credit: Columbia Pictures.

Seth Rogen, James Franco, and Danny McBride star in this comedy about a recreational drug enthusiast on the run after witnessing a murder. True to their sort of comedy, Rogen, Franco, and McBride bring the laughs as they try to escape from the murderers. Franco and Rogen don’t collaborate on wits anymore, so it’s unlikely this one will get a sequel.

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