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Sunday, October 1, 2023

Adam Sandler’s Best Movies From the 2000s

The new millennium was a wonderful time. Ripe with possibility and carrying a refreshing sense of creativity, the decade left behind the ‘90s and allowed new things like technology and pop culture to enter. It was a time of social media, bracelets, and sk8er fashion. Things were finally fun again. Amidst it all, the entertainment industry was paving the way for actors who would continue to endure in their signature goofy, feel-good way.



While Adam Sandler had been steadily honing his brand of charming man-child humor through the ‘90s, it was in the 2000s that he hit full stride. After being surrounded by an influential group of co-stars on and off the sets of Saturday Night Live, Sandlar chose to channel the same stardom into film and secured his place as a beloved actor. His sweet and silly personality paired with a carefree wardrobe made him instantly likable.

For many viewers, Adam Sandler’s movies are comforting. Often appearing in slice-of-life romances, he made comedy accessible to living rooms and streaming services. The stories he told were heartwarming and time-relevant, and the characters he played were earnest and funny. As the era drew to a close and the trends began to change, Sandler’s output in the 2000s turned out to contain movies that encapsulated the culture and aesthetic of the decade. And what better time to revisit it than now?

10 Grown Ups (2010)

Adam Sandler in Grown Ups
Sony Pictures Releasing

The movie that won Adam Sandler a People’s Choice Award for Favorite Comedic Movie Actor is often ridiculed for its silly premise, but we all know the actor has a distinguished way of shining in that area. There’s a lovely air of nostalgia in Grown Ups, which centers around five childhood friends whose glorious days of adolescence and high school are nothing but forgotten memories. Now married and settled in their careers, the friends reunite to attend the funeral of their high school basketball coach and visit their hometown with their spouses and kids.

The movie shows their male camaraderie passed down to the children as well because the chemistry they share is truly beautiful. Along with the rest of the comedic cast, Sandler anchors this heartwarming story and infuses it with scenes like pulling pranks and having fun outdoors.

9 Funny People (2009)

Adam Sandler & Seth Rogen in Funny People
Universal Pictures

Funny People features some of the funniest actors in the industry, and with Judd Apatow’s sublime direction, the film is a pure masterpiece. Charting the territory of mature comedies, the film stars Sandler as a mega-comedian recently diagnosed with a terminal illness. While most people at his status would spend their remaining time reflecting on past joys and regrets, George Simmons decides to take an aspiring comic (Seth Rogan’s Ira) under his wing and show him the ropes.

Through several sessions, Simmons trains Ira in stand-up comedy and how to pack a punch in a set. With Leslie Mann’s old flame entering the picture and Simmons’ cancer in control, the movie moves in an entirely different direction then. Apatow’s script is enhanced by performances from Jonah Hill, Eric Bana, and Aubrey Plaza.

8 Bedtime Stories (2008)

Adam Sandler in Bedtime Stories
Walt Disney Studios Motion Pictures

If you’re a genuine Adam Sandler fan, you won’t listen to the critics who brand Bedtime Stories as a movie filled with saccharine stuff. You’d know that the movie is one of Sandler’s top five movies. Directed by Adam Shankman, this wholesome Disney film revolves around Skeeter Bronson, a hotel handyman whose bedtime stories for his young niece and nephew start coming to life hilariously and wonderfully.

Hoping he can get himself and the kids out of this puzzle, Bronson weaves his storytelling accordingly, only to fall deeper into the rabbit hole. Supported by an endearing cast including Keri Russell, Teresa Palmer, and Russell Brand, the movie takes you on a ride. It doesn’t even matter if you’re a kid or an adult because Sandler will make you smile.

7 Reign Over Me (2007)

Adam Sandler in Reign Over Me
Sony Pictures Releasing

Written and directed by Mike Binder, Reign Over Me is a buddy drama starring Adam Sandler and Don Cheadle. Following the devastating events of 9/11, Sandler finds himself torn after losing his wife and daughters in the attacks.

While overcoming the tragedy is weighing him down, an awkward reunion with his college roommate, Alan Johnson (Cheadle) helps him heal and come to peace with his internalized grief. The movie is as subtle as it is authentic. It guides you around the beautiful premise with emotion and then strips itself of any pretense and showcases just how brutal life can get when you’re alone. Sandler’s performance is empathetic and respectful towards every person who grieved their losses, which is perhaps another thing that makes the film so good.

6 Click (2006)

Adam Sandler in Click
Sony Pictures Releasing

Fantasy hasn’t looked more joyous and thought-provoking than in this 2006 film by Frank Coraci. As an overworked architect, Michael Newman is always faced with complaints from his wife and children that he never makes any time for them. But when he stumbles upon a universal remote control that allows him to fast forward or rewind any portion of his life, Newman has fun with it.

But you know how these things work. Or don’t work. Soon, the remote begins to override Newman’s commands and he’s faced with complications. Adam Sandler infuses his character of a father and a husband with nuance and thriller. And while Clickdoes work best as a comedy, its sentimental value cannot be ignored.

Related: The 10 Best 2000s Movies That Exude Y2K Vibes

5 The Longest Yard (2005)

Adam Sandler in The Longest Yard
Sony Pictures Releasing

Burt Reynolds may have manufactured the formula for this prison football classic in 1974, but Adam Sandler sure steps up to bring more laughter and more emotion in this remake. The Longest Yard follows Adam Sandler playing Paul Crewe, a disgraced NFL quarterback who lands himself in jail.

Challenged by the warden and encouraged by an inmate, Crewe ends up coaching and orchestrating a match between the inmates and the guards. James Cromwell, Adam Sandler, and Chris Rock trade playful insults and emerge as the ultimate buddy cop trio in the movie. Despite its unconventional setting, the film has this gorgeous underdogs-winning-against-all-odds vibe that makes it all the more exciting.

4 Spanglish (2004)

Sony Pictures Releasing

James L. Brooks wrote the screenplay for and directed this unique slice-of-life movie starring Adam Sandler and Téa Leoni. Flor Moreno is a Mexican single mother who recently moved to America with her daughter, Christie, so that they can live a carefree life. She starts working at the Clasky home, run by an obnoxious but kind Deborah and her husband John, living with their two children.

The first few days, the household runs smoothly, but soon Flor mentions that she can’t keep up with the schedule because she also has to take care of her daughter. To which, the Claskys suggest that Flor and Christie can come live with them. Torn by culture and creativity, the families have candid moments and dysfunction in equal proportion. Beyond being authentic and comforting, Spanglishalso has the sharpest dialogues ever.

3 50 First Dates (2004)

Drew Barrymore and Adam Sandler in 50 First Dates
Columbia Pictures

From the director of The Longest Yard and Anger Management, we have this quintessential romantic comedy that redefined the 2000s as an era of love. 50 First Dates stars Adam Sandler alongside Drew Barrymore, and it follows the former playing Henry Roth, a young veterinarian. Despite being a ladies man, Henry has his heart set on a local girl named Lucy. Lucy is somewhat of an oddball.

Because of her short-term memory loss, she can’t remember any moment from the day before so Henry has to try to impress her every day. Her resetting mind and his tape-recording explanations make for a charming chemistry. To witness their romance going back to square one is truly delightful.

2 Anger Management (2003)

Adam Sandler and Jack Nicholson in Anger Management
Sony Pictures

Have you ever had an anger fit so intense you’re holed up with a therapist in your house? No? Well, Adam Sandler’s character in Anger Management has. Directed by Peter Segal, this crowd-pleaser follows Dave Buznik, who loses his sh*t when on a plane.

But instead of being sent to jail, he is sent to an anger management expert who claims that he can treat his short-fused personality. Dr. Buddy Rydell is played by Jack Nicholson. Rydell is a quirky man and an unconventional therapist who moves into Buznik’s house to stay with him 24/7 and help him fight his inner demons. Being comedic icons themselves, both Sandler and Nicholson bring magnificent chemistry to the screen, leaving the audience agape.

1 Punch-Drunk Love (2002)

Columbia Pictures

The best way to close up this list is with a Paul Thomas Anderson movie. With Punch-Drunk Love, the director crafts a beautiful story of love. It stars Adam Sandler as Barry Egan, a shy bathroom supply business owner who often spends his time alone for two reasons – he is a volatile person and he is ridiculed by his seven sisters.

However, Egan is bent on changing his life. The occurrence of one particular incident – him using an adult phone service and falling in love with Lena Leonard, one of his sister’s colleagues – works for his cause. The movie constantly fixates on mankind’s primal need for affection, and while several films have navigated this territory, what makes Punch-Drunk Love stand out is the eerie score, dreamlike visuals, and astonishing performances from Sandler and Emily Watson.

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