Labor Day is often seen as the official end of summer, a time for one last hurrah before the cooler months roll in. It’s a chance to take that final weekend road trip, soak up the sun at the beach, or unwind with a great movie. But why not make it a truly memorable Labor Day with some hilarious comedies? Whether you’re in the mood for office shenanigans, a chaotic family vacation, or a hilariously bad shark movie, these five films are sure to have you laughing all weekend long.
White Chicks (2004)
For many East Coast socialites, Labor Day means a trip to the Hamptons for glitzy parties and extravagant gatherings. But *White Chicks* takes a hilarious swipe at this world, poking fun at the vapid lifestyles and petty social drama of America’s elite. The Wayans brothers play undercover FBI agents who must infiltrate this exclusive social scene, posing as white women to protect a family that might be in danger. The film is a brilliant satire of the over-the-top world of socialites and the catty girl culture that dominated the 2000s. It’s a masterclass in punching up, offering comedic commentary on a culture that often deserves a good laugh. Catch *White Chicks* on Netflix.
The Way Way Back (2013)
Nothing feels more quintessential Labor Day than a trip to a charming New England seaside town. In *The Way Way Back*, a shy young boy named Duncan spends a summer vacation with his mom and her new, rather unpleasant boyfriend. As Duncan navigates the challenges of a dysfunctional family dynamic and the pressures of fitting in, he finds solace and self-discovery through the kindness of the people he meets in the town and at his summer job. The film is a beautiful blend of comedy and coming-of-age story, resonating with anyone who’s ever felt like an outsider. The incredible cast, featuring Toni Collette, Steve Carell, Allison Janney, Maya Rudolph, and Sam Rockwell, adds even more depth and humor to the experience. You can find *The Way Way Back* on Paramount+.
Jaws: The Revenge (1987)
Now, you wouldn’t think *Jaws: The Revenge* was meant to be a comedy, but it’s undeniably one of the funniest movies ever made, unintentionally of course. The film centers around Ellen Brody, the widow of Chief Brody from the first two films. After witnessing firsthand the terrifying power of a giant shark, she is understandably cautious around the ocean. But the film takes a hilarious turn as she travels to the Bahamas, a destination that seems particularly unwise given her shark-induced PTSD. The shark itself adds to the comedic absurdity. It appears in some scenes as a bobbling toy, in others it magically glides through the air. The climax is truly a sight to behold, with the shark standing upright in the ocean and emitting a terrifying roar. If you’re looking for a truly outrageous laugh, *Jaws: The Revenge* on Max is the way to go.
Clockwatchers (1997)
While Labor Day is a celebration of leisure, it’s also a reminder of the American workforce and the rights they fought for. To truly honor the holiday, consider watching *Clockwatchers*, a film about the mundane lives of four office temps. Their routine takes a comical turn when office supplies mysteriously disappear, leading to a series of humorous misadventures. The film’s strength lies in its phenomenal cast, including Parker Posey, Lisa Kudrow, and Toni Collette. While more mainstream workplace comedies like *Office Space* or *The Devil Wears Prada* might be familiar, *Clockwatchers* is a hidden gem, a witty and insightful indie comedy that deserves a second look. You can watch *Clockwatchers* for free on Peacock and Tubi.
Vacation (2015)
*Vacation* isn’t a reboot, but a sequel, picking up decades after the original films. Rusty, all grown up, decides to take his own family on an epic cross-country adventure in the spirit of his father’s notorious road trips. As you might imagine, the Griswold family’s trip quickly descends into chaos. From Arkansas to the Grand Canyon, San Francisco, and even Wally World, the Griswolds encounter a series of hilarious mishaps across America. The original cast members, Chevy Chase and Beverly D’Angelo, reprise their roles as Clark and Ellen, alongside a talented ensemble that includes Ed Helms, Leslie Mann, Charlie Day, Regina Hall, and Chris Hemsworth. Catch *Vacation* on Max.
