First-Class Adam Sandler Movies You Can Watch Over And Over

7 minute read

By James Sheldon

Adam Sandler was once considered the most adored celebrity in the entertainment industry. Yes, he’s still beloved for what he has done, but not so much for what he is doing. For those coming to Adam Sandler party late: no, he didn’t always make terrible movies. His recent obsession with casting his closest friends to take care of his closest friends has somewhat spoiled a lasting legacy, but if you want proof that he’s done some excellent stuff, check out the following 10 movies!

10. I Now Pronounce You Chuck and Larry (2007)

We’ll start in the gray area of the Adam Sandler library. I Now Pronounce You Chuck and Larry could easily be tossed into another category of Sandler’s biggest flops. But the sentiment was sincere, and the comedy of errors played well, making it a watchable movie. We won’t go so far as to call it a film. Adam was bound to take advantage of his funnyman friend, Kevin James, and this one worked well for the two of them. Adding names like Jessica Biel and Ving Rhames to the mix certainly didn’t hurt the box office punch. And of course, Sandler movie regulars, Steve Buscemi and Dan Aykroyd were injected into the on-screen magic. If you haven’t seen it, two straight NYFD veterans pose as a gay couple in order to enjoy partner benefits, and the comedy unfolds. Via sky.comSource: Screenshot via Universal Pictures

9. Billy Madison (1995)

While many will experience a knee-jerk reaction to Billy Madison being listed at #8 on this list, at least it’s on this list…and deservedly so. Billy Madison introduced us to the Adam Sandler-led feature film, and as bad as some of the movie is from a general, filmmaking perspective, nobody was hoping this film would break new ground. Every once and a while, we all need to laugh at some crass humor, and a bunch of dick and fart jokes. Billy Madison has no shortage, and it has no shortage of talent who are willing to go with Adam on his romp through absurdity. This includes the late, great Chris Farley, as the world’s greatest school bus driver. Adam Sandler plays Billy, a definitive brat who never grew up, and only finished school due to his father’s influence. To prove his worth, Billy goes back to school, beginning with kindergarten. Via RollingStoneSource: Screenshot via Universal Pictures

8. Click (2006)

The ‘Click’ story is nothing new. It takes several ideas from classic literature, as well as films that came before it. It features a man obsessed with all the wrong things finally coming to terms with how short life actually is. Adam employed another pretty stellar cast for this outing, including legendary voice actress, Julie Kavner, who played his mother. Julie is most recognizable as the voice of Marge Simpson. Additionally, Adam also pulled some strings to score Kate Beckinsale as his wife, Henry Winkler as his father, and David Hasselhoff as his boss. Christopher Walken plays some weird dude representative of the all-knowing, which is pretty much Chris Walken playing Chris Walken. It always works. Via justwatch.comSource: Screenshot via Sony Pictures Releasing

7. Happy Gilmore (1996)

Happy Gilmore is a fine example of Adam Sandler hitting his stride, and the working toward the peak of his popularity in the 1990s. This was the first film released after Adam left the cast of Saturday Night Live, following a five-year residency, and it thrust Adam into the eyes of an entirely new audience. Instead of being a fixed commodity of the 18-34 demographic, he made a movie about a former hockey wannabe becoming golf pro and lured the baby boomers to the theater. Similar to its predecessor, Billy Madison, Happy Gilmore is far from a perfect film, but again, who really cares? We’ll take Adam Sandler and Bob Barker doing hand-to-hand combat any day. Happy Gilmore has also survived a 20-year test of time, and is regularly referenced on the sports network boasting four letters, and quoted often by those stinking up the golf course. Via TVGuide.comSource: Screenshot via Universal Pictures

6. 50 First Dates (2004)

When Adam Sandler and Drew Barrymore are at their best, they are two of the most engaging, likable movie stars to have ever graced the silver screen. 50 First Dates worked, and it was a bit of a bait and switch. The film begins as a traditional Sandler comedy, laden with over-the-top absurdity, but into the second and third acts of this surprisingly sentimental comedy, the story dives below the surface to spotlight some medical issues that plague a select few people, and that charge is led by the incomparable Dan Aykroyd, as the doctor to Drew Barrymore’s character. Sure, if you’re a cynic, this movie only annoys you, but if you’re capable of adjusting perspective, it’s easy to imagine this film surviving the test of time. Sadly, the third collaboration between Adam Sandler and Drew Barrymore, Blended, didn’t play out like the first two.

Source: Screenshot via Sony Pictures Releasing

5. The Waterboy (1998)

“You can do it!” Another film frequently referenced on “the network,” The Waterboy was a very pleasing film effort for football fans. Too many times, filmmakers, and TV producers attempt to offer quality football to the screen, and it just doesn’t work. That’s one of the reasons football comedies tend to do better than dramas. For the love of the ghost of Vince Lombardi, please, let there never be another football movie like The Program. The Waterboy remains a guilty pleasure. Colonel Sanders, and the baseball through the window? One of the greatest two seconds in cinematic history. And every fan of “The Fonz” is so thankful that Adam insisted they grab Henry Winkler to play the (now) legendary Coach Klein. This motion picture is best enjoyed in late August, just before the start of the new NCAA Football season. Via Sky.comSource: Screenshot via Buena Vista Pictures

4. Big Daddy (1999)

Think back to the summer of 1999. It was a summer of icons, and iconic disappointments. Star Wars Episode 1: The Phantom Menace disappointed everyone, but the gang from American Pie didn’t when they delivered one of the most outrageous, and testosterone-charged comedies since Screwballs. Theaters projected the final Stanley Kubrick film, Eyes Wide Shut, and Adam Sandler offered up one of his most enjoyable wheelhouse efforts to date: Big Daddy. Sandler is a family man, and he loves to push the agenda. It’s one reason so much of his early stuff worked when he ventured into the realm of sentimental comedy. It is rather evident in all of his projects, and it is completely universal. In this particular film, he’s roped into playing the father to an orphaned child and grows from being a man-child to a man in the process. Via Sky.comSource: Screenshot via Sony Pictures Releasing

3. The Wedding Singer (1998)

There’s something pretty special about a 1980s period piece being made in the late 1990s. Possessing an obvious sweet-spot for the era, Adam Sandler has dropped about a million 1980s references throughout his body of work in TV and cinema. The Wedding Singer is like a fluorescent highlight marker across the decade in the form of a film, featuring a down on his luck wedding singer, his band, the girl he falls in love with (Drew Barrymore), and the fact that she’s betrothed to a real Miami Vice wannabe. The Wedding Singer was a show of promise for Adam Sandler’s fledgling Happy Madison production company. (It wasn’t technically a production, but it helped give birth to HM.) The cast of support characters are what made The Wedding Singer fly. Christine Taylor may have been at her best.

Source: Screenshot via New Line Cinema

2. Spanglish (2004)

There’s something about Spanglish that grows on a viewer. It’s not overly impressive during a first viewing, but it’s a film that resonates. For those who are used to seeing Adam Sandler yuck it up with the boys, a film like this will take a little adjustment from the audience’s perspective. This is far from a Happy Madison production, written and directed by comedic genius James L. Brooks, yet it’s not really a comedy. Sure, it’s classified as a comedy or dramedy, perhaps, but it’s not a surface level romp we’re so used to seeing Adam in. In Spanglish, he stars as a renowned chef, John Clasky, and the film explores the family dynamic of the Claskys, as well as their housekeeper, and her daughter Flor (Paz Vega) and Christina Moreno. It’s complex, funny, sad, uncomfortable and quite enlightening. Via YouTubeSource: Screenshot via Columbia Pictures

1. Punch Drunk Love (2002)

When Paul Thomas Anderson announced he was casting Adam Sandler in his 2002, weirdly dark, romantic comedy, it was cause for pause. Anderson was looking to get as far from the cinematic experience of Magnolia as possible, while still offering something of impressive quality. Anderson’s work is never short of whimsy, or uncanny moments and Punch Drunk Love provides more than a few. Adam Sandler was perfectly cast as Barry Egan and offered a tour de force when considering the grand picture of his career. For the hardest of the hardcore film buffs and critics, they were pleasantly surprised by Adam’s performance in the film. We’re imagining Adam enjoyed the experience, but not enough to set aside his attempts at making more raucous comedy for the sake of box office success. That stated, another film like this is precisely what Adam needs at this point in his career. Via hopelies.comSource: Screenshot via Sony Pictures Releasing

James Sheldon


James Sheldon has been writing about music, movies, and TV for Goliath since 2016.