An Escapist Vacation Guide Through Adam Sandler’s Happy Madison Movies

Call him lazy, call him a capitalist genius — either way, The Sandman has mastered the art of getting paid for going on vacation

No entertainer is a bigger fan of baggy clothes and vacations than Adam Sandler. In a legitimately brilliant mix of capitalism and work days that require getting hit in the nuts a few times, the head honcho behind film production company Happy Madison has found a way to mix business with sightseeing and staying at the nicest resorts, all on the dime of major studios like Netflix.

There’s no better time, then, to vacation vicariously through Sandler’s movies than during a pandemic. Across numerous films in the Happy Madison filmography, he’s provided what is virtually a vacation cinematic universe, starring a bunch of gorgeous tourist spots and his friends David Spade, Kevin James, Jennifer Aniston, Drew Barrymore, Rob Schneider and more. Bright sunlight, product placement (sometimes for Pepto Bismol) and comedic sequences built around watching Sandler and his on-screen family get a little tropical R&R is practically guaranteed. 

In honor of Happy Madison’s special dedication to cinematic escapism, we’re looking back at the most major trips that Sandler’s company has put together for his friends and, to a much lesser extent, your entertainment.

Honolulu, Hawaii, ‘50 First Dates’ 

This isn’t a vacation movie for one of Sandler’s characters, but 2004’s 50 First Dates warrants inclusion here, because this is where the tradition of Sandler’s paid vacations started. The original script was supposed to take place in Seattle, and naturally, it was Sandler’s idea to put it in a different place. “Yeah, that’s a very artistic idea,” he was told. And thus, 50 First Dates was rewritten for the sunnier cafes and homes of the island of Oahu, in and around the likes of Kaneohe, Ka’a’awa, Wahiawa, Honolulu and Kāne’ohe Bay. Given the film’s loving depiction of Hawaii as a place to live and not just visit for a few days, it’s no coincidence that this is one of Sandler’s sweetest movies.

Maui, Hawaii, ‘Just Go With It’ 

Sandler returned to Hawaii for a second film vacation with 2011’s Just Go With It, in which he plays a cranky plastic surgeon who wants to manipulate a younger woman (Alice Eve) into being with him, which he does by also manipulating a co-worker (Jennifer Aniston) and her two kids to pretend to be his ex-wife and children, respectively. This movie heads for the Waldorf Astoria’s Grand Wailea Resort around 45 minutes in, because where else are you going to try to execute a scheme of having a fake family and ex-wife? 

Much of the bonding takes place on the resort grounds, but there is one adventure sequence that has them kayaking, hiking and going to a waterfall at Kilauea Falls, which is actually on a different island. There’s a lot of cringeworthy stuff about this movie, but the worst might be that it offers further evidence that Sandler is a resort vacationer — even if he’s in a beguiling place like Maui, he’d prefer to just hang out by the pool. 

Royal Caribbean Cruise, ‘Jack and Jill’

In 2011, Sandler was able to get his on-screen family (and presumably his real-life one) on a cruise ship that was still in its pre-inaugural celebrations. Jack and Jill stars two Sandlers as feuding twins, but it gives the most loving screen time to Royal Caribbean’s Allure of the Seas, which is now one of the world’s largest cruise ships. True to what one of Sandler’s on-screen progeny exclaims, “This boat has everything!,” including mini-golf, an all-you-can-eat buffet, a gym, a giant pool, rock climbing, a carousel and more (all of this is shown in the movie — you know, for narrative purposes). The commercial intent was so heavy that Royal Caribbean even offered one lucky winner their own Jack and Jill inspired cruise vacation, presumably without Al Pacino making an appearance via helicopter.   

Sun City, South Africa, ‘Blended’

The farthest that Sandler has taken his Happy Madison crew was for Blended, a 2014 family comedy (starring Sandler and Drew Barrymore) about single parents whose families become enmeshed together. Like with other Happy Madison projects, the star of this movie is the resort, which in this case is the Lost City at Sun City Resort. The activities are a mix of Happy Madison shenanigans (accidentally seeing two rhinos fuck; watching monkeys play a ramshackle rendition of “Careless Whisper”; and a slew of stereotypical images of Africans) and actual resort activities, like dinner at the Crystal Court. In one of the more shameless plugs in Happy Madison lore — maybe even worse than Jack and Jill — they even take time to show off the resort’s jungle play zone, nightly pool party and disco. 

Still, the shoot wasn’t without its dangers. On Late Night with David Letterman, Sandler talked about how he was offered to give water to a cheetah. But when he bent over, the cheetah attacked him from behind — you can see it all on video. 

Las Vegas, ‘Paul Blart: Mall Cop 2’

After saving a New Jersey mall from skateboarding thieves, the next adventure for Kevin James’ vigilante takes him to Steve Wynn’s 2005-established Wynn Casino, where Blart gets to play tourist for a security cop convention, even though his heroics are inevitably called upon (never forget the age-old Blart credo: “Security is a mission, not an intermission.”) The antics that take place in Paul Blart: Mall Cop 2 (which Sandler produced) are all based in the Wynn and its sister tower, the Encore, putting Blart in front of a plate of double chicken parm at the Bartolotta restaurant (now known as the Costa di Mare), or showing off his Segway skills in the Wynn esplanade, in clear view of Cartier and Dior stores. And while evading some bad guys, Blart finds himself at the center of the casino’s resident Cirque du Soleil production La Rêve, an aquatic show on the premises. 

But you have to wait until the end to see the guy who made it all happen — Steve Wynn. He appears in a wordless cameo opposite James, playing the meta role of “guy who hands over a big check.” 

Puerto Rico, ‘The Do-Over’ 

David Spade and Sandler buddied up for 2016’s The Do-Over, a type of faked-death fantasy that calls for a different kind of getaway. The key to their reinvention is taking on the lives of people who live in Puerto Rico, so cue the montage of Old San Juan, which includes a drone shot over the amazing Castillo San Felipe del Morro that lies on the edge of the city, and images of women in bikinis. In true Happy Madison fashion, the sense of local culture is essentially, and sadly, abandoned from there. Instead, Puerto Rico gets a bleaker significance — a means for their middle-aged men to take a vacation from their sad-sack existence. 

Milan, Italy, ‘Murder Mystery’

It’s a little surprising that Sandler hasn’t embraced European vacations more, as the sightseeing in the unmistakably titled Murder Mystery is genuinely fun, and it inspires more excitement than just watching Sandler and his friends hang out in a super fancy hotel. Murder Mystery has Sandler and Aniston (as two long-married people thrown into a, well, you know) begin their accidental yacht adventure in the gorgeous port town of Santa Margherita Ligure. The script’s whodunit scenario then transplants everyone to the picturesque Milan (which does stand-in work for Monaco) and later to Lake Como, where Sandler takes part in a rare chase scene that ends with him tripping and crashing into a cart. And for all of you fans of the Italian buildings also used in Ocean’s Twelve, the climax of the movie was shot at Villa Erba, a 19th century lakefront property that you can only visit if you’re a part of a wedding there.

Oahu, Hawaii, ‘The Wrong Missy’ 

Spade wasn’t a part of 50 First Dates or Just Go With It, so he got a Hawaiian getaway with The Wrong Missy, a movie that has him and comedian Lauren Lapkus slap-sticking around the Four Seasons Resort Oahu, at Ko Olina. In this most recent Happy Madison Netflix comedy, Spade is an uptight business guy who accidentally invites a different Melissa than he intended to a work retreat. Beach-side, pool-side and shadow-dancing antics then ensue. 

Heavy sigh. 

While much of the movie takes place at the hotel, there’s a historic shark scene (at least within the history of nautical vomiting), in which Spade is in a shark cage with his boss. Part of the scene is thanks to a real tourism company in Oahu, Dolphins and You. As they affirm on their website: “We’ve never seen a large shark in the water … we promise our practices are much more sanitary. On a real Dolphins and You tour, there’s a lot more dancing, a lot more culture and a lot more dolphins!” 

For all of Sandler’s cultural tone-deafness and creative license, hopefully at least tourism businesses like Dolphins for You, and locales like Oahu, Puerto Rico and South Africa benefit from serving as Happy Madison backdrops. When we can all actually go on vacation again, that is.