Rewatch These 25 Movies Turning 25 Years-Old In 2024

Tom Cruise and Nicole Kidman play a married couple (the pair were also married in real-life at the time) in this Stanley Kubrick film, the director’s last. In it, Cruise’s character embarks on a wild night, infiltrating New York’s secret underground of the wealthy. The tension crackles throughout and it’s one of Cruise’s best performances.

Brad Pitt is a bad boy who ropes straight-laced Edward Norton into forming an underground fighting ring. Or is he? This movie requires two viewings so you can take it in before and after you know the twist.

Shakespeare has never been as much fun as it is in this reimagining of “The Taming of the Shrew.” Julia Stiles and Heath Ledger both pop as teens moving from hate to love and one memorable song scene, where Ledger’s Patrick declares his love in a stadium, made us swoon.

If you only know Ripley through the Netflix TV series, check out this other super stylish adaptation of the Patricia Highsmith novel where Matt Damon plays a con artist who worms his way into the lives of a rich couple (Jude Law and Gwyneth Paltrow) living on the Amalfi coast. If this doesn’t make you book a trip to Italy, then nothing will.

A remake of the Steve McQueen caper, this version about an art heist is far better (and sexier for that matter). Pierce Brosnan and Rene Russo have smoldering chemistry, amazing wardrobes and lots of scenes spent sans wardrobes.

Jim Carrey utterly transformed himself into bizarro comedian Andy Kaufman and this is probably one of his best dramatic roles. Courtney Love brings her softer side to the film as his girlfriend Lynne.

The lives of sad residents of the San Fernando valley intersect in this film by Paul Thomas Anderson. The star-studded flick is set to a soundtrack by Aimee Mann (whose lyrics inspired the film), upping the melancholy to new heights. This is the perfect watch when you want to wallow.

The plot of Big Daddy is rather cringey: Adam Sandler pretends a little boy is his son to get his girlfriend back, but it’s the cute interactions between Sandler and twins Cole and Dylan Sprouse (who took turns as Julian) that make this a classic.

She’s just a girl standing in front of a boy — but the girl is Julia Roberts and the guy is Hugh Jackman, at their cutest — in this cozy London romance about an actress who falls in love with an average bloke.

A film probably before it’s time, it tells the true story of Brandon Teena, a trans man who falls in love, only to become the victim of a hate crime. Hilary Swank won the Academy Award for Best Actress and Chloë Sevigny was nominated for Best Supporting Actress.

From the twisted minds of Spike Jonze and Charlie Kaufman is this whimsical film about a puppeteer (John Cusack) who discovers his office is a portal into the mind of actor John Malkovich. Cameron Diaz and Catherine Keener also star.

Since this film, where humanity is unknowingly trapped in a simulated reality, there are people who believe that it may be a true story. We can’t necessarily prove them wrong, but we can say that this film cemented star Keanu Reeve’s career as an A-list action star. Three more Matrix films have since followed.

Achingly beautiful with a dreamy soundtrack, this debut film by Sofia Coppola made her a director to watch. It also made Kirsten Dunst, who plays one of the five Lisbon sisters featured in the film, leading lady material.

This chilling thriller, about a kid who can see ghosts, still holds up and is actually even better when you know the twist. Bruce Willis, Haley Joel Osment and Donnie Wahlberg all give incredible performances and the film kicks off director M. Night Shyamalan’s career with a bang.

Drew Barrymore is peak adorable as Josie, a woman who goes back to high school for a journalism assignment and gets to live the life of a teenager much cooler than she actually was. Surprisingly, the film was based on a true story.

Nothing should come between a boy and his giant robot, not even the U.S. military. Director Brad Bird made his directorial debut with this cult animation classic and went on to direct “The Incredibles.”

Woody accidentally ends up in the hands of a toy collector in this sequel, but we also get to meet Jesse and Bullseye in this essential “Toy Story” chapter.

This Universal monster movie, starring Brendan Fraser, is a remake of a 1932 movie and was rebooted again in 2017 by Tom Cruise, but I think we can all agree this one is the best.

It’s hard to believe some essential pop culture characters didn’t get introduced until this sequel to “Austin Powers,” but we couldn’t imagine any of these movies without Mini-Me. Is this “The Empire Strikes Back” of silly comedies?

A grieving mother, an actress, the actress’s lover and a pregnant nun all find common ground in this Pedro Almodóvar masterpiece, yet another of his collaborations with longtime muse Penélope Cruz.

Randy teen boys make a pact to lose their virginity by graduation, thereby launching the careers of Jason Biggs, Chris Klein, Alyson Hannigan, Natasha Lyonne, Thomas Ian Nicholas, Tara Reid, Mena Suvari, Eddie Kaye Thomas, Seann William Scott, Shannon Elizabeth and Jennifer Coolidge.

It’s probably one of the worst "Star Wars" prequels but it’s still a "Star Wars" prequel. It sets up the trilogy to come and introduces us to Queen Amidala, young Anakin Skywalker and a young Obi-Wan like we’ve never seen before. Also, Jar Jar Binks (womp womp).

This found-footage film made us never want to walk in the woods again and kicked off an entire genre of found-footage horror. The film cost less than a million to make and earned over $248 million so it was a monster hit.

Several of the lines in this office comedy became mantras of the young working generation and it spawned so many memes. Swingline even made a stapler that looked just like Milton’s, the breakout character of the film who was obsessed with his office supplies.

Reese Witherspoon’s Tracy Flick, a teen obsessed with school elections, is the mirror villain of her other famous character, Elle Woods.