10 Movies Turning 20 In 2026 That You Have To Rewatch

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It was a simpler time in 2006. Songs like "Every Time We Touch" by Cascada, "Welcome to the Black Parade" by My Chemical Romance, and "Ms. New Booty" by Bubba Sparxx (featuring the Ying Yang Twins) were dominating eighth grade dances. Barry Bonds surpassed Babe Ruth's Major League Baseball all-time record by hitting his 715th career home run. And before they became the divisive trash fires they are today, the general public was just starting to discover the newly-launched social media platforms known as Facebook and Twitter.

It was also another banner year for the movies. Masters of the craft like Spike Lee, Sofia Coppola, and Richard Linklater captivated audiences with their latest works. Fan-favorite filmmakers Jason Reitman, James Gunn, and the Duplass Brothers presented the directorial debuts that launched their careers. Shortly after the Walt Disney Company purchased Pixar, the world was introduced to a rambunctious race car and his tow truck bestie as they fueled up the massive global franchise that would spawn sequels, theme park attractions, and Rascal Flatts' version of "Life is a Highway" with "Cars."

While it's hard to imagine that the adventures Lightning McQueen and Mater are turning 20 years old in 2026, there are a ton of films from that year that are celebrating that milestone as well and are certainly worth revisiting. Some of them even warrant multiple viewings. With that in mind, here is a list of movies from 2006 that have endured two decades and deserve a rewatch or two.

Starting in 1997 with "Under Wraps," Disney Channel Original Movies rose to prominence. Kids of the late 1990s and early 2000s sang the praises of classics like "Brink!," "Johnny Tsunami," "Motocrossed," and the "Halloweentown" trilogy. Although, not literally because these staples of tween cable cinema weren't typically musicals like the House of Mouse's beloved major motion pictures (with the exception of "The Cheetah Girls) in 2003). However, all that changed in 2006 with the arrival of "High School Musical."

Long before DCOMs like "Teen Beach Movie" and "Camp Rock" or the Fox series "Glee" premiered, Troy Bolton and Gabriela Montez ushered in a new age of musicals for teenagers. Not that it was ever uncool to do musical theater, but seemingly more kids were loud and proud of their fandom thanks to the characters portrayed by Zac Efron and Vanessa Hudgens who came from two very different worlds (sports and academia) to find love for each other and the fall musical.

The movie's powerful message to unapologetically be who you are, paired with catchy songs and memorable dance numbers from acclaimed choreographer-turned-director Kenny Ortega, is really what made the film stick with its audience. While the script is essentially a nearly beat-for-beat modern retelling of "Grease" (which itself is basically a musical retelling of "Romeo & Juliet" minus the tragedy), screenwriter Peter Barsocchini and composer David Lawrence updated this tale as old as time for a new generation of viewers.

Whether you're looking to relive your younger days or you've reached a point where you have a teenager who could benefit from hearing the Wildcats' story, you might say "High School Musical" is what I've been looking for.

This probably goes without saying, but Martin Scorsese is one of the greatest filmmakers ever. With a career spanning over 50 years, many entries on his filmography are considered to be among the best movies of all time. In fact, projects like "Taxi Driver," "Raging Bull," and "Goodfellas" are foundational elements of any education in cinematic storytelling. But if each of those movies represented a masterpiece from each decade he has been active in the film industry, then the next movie in the pattern would most certainly be "The Departed."

A remake of the acclaimed Hong Kong crime drama "Infernal Affairs," director Scorsese and writer William Monahan also loosely based their award-winning movie on the real-life Boston Winter Hill Gang. The film features Jack Nicholson as mob boss Frank Costello as he plants a spy (played by Matt Damon) among the ranks of the Massachusetts State Police. Meanwhile, the cops assign Leonardo DiCaprio's Billy Costigan to infiltrate Costello's operation.

Obviously, Scorsese has dabbled in the world of organized crime before, but "The Departed" feels grittier and more psychological than some of his previous work. It also helps when he has an impressive cast that also touts Mark Wahlberg, Martin Sheen, Ray Winstone, Alec Baldwin, and Vera Farmiga among the ensemble. They managed to take the grim, often fatal subject matter and somehow authentically infuse levity into the happenings that come along with undercover work. On top of these all-star performers delivering the lines, it's no wonder that Monahan's script earned the Academy Award for Best Adapted Screenplay.

For fans of Scorsese or mob movies in general, this is definitely worth a rewatch every so often.

When people think about comic book movies, it's likely that they picture Batman, Superman, or The Avengers adorning the poster. But 2006 wasn't a great year for those kinds of movies, as that was the year that "X-Men: The Last Stand" and "Superman Returns" debuted. However, one of the best stories to make the jump from your local comic book shop to the megaplex also premiered during that same year, and even 20 years later, despite its creator's objections and the departures from the source material, "V For Vendetta" may go down in history as one of the greatest comic book movies of all time.

Based on the best-selling Vertigo Comics limited series by Alan Moore, David Lloyd, and Tony Weare from the 1980s, this dystopian thriller follows a freedom fighter in a Guy Fawkes mask named V as he carries out an elaborate plan to inspire a revolution and take down the fascist government in an alternate 1990s United Kingdom. The film adaptation starring Natalie Portman, John Hurt, Stephen Rea, and Hugo Weaving also has a lot to say about the political climate at the time of its release. Unfortunately, the themes of fear mongering, media manipulation, and corruption have persisted, making this movie as relevant as ever.

As the old saying goes, those who don't learn from history are doomed to repeat it. To supplement the lessons we take away from domestic and global history, it might be worth it to revisit "V For Vendetta" often to remind ourselves that people should not be afraid of their governments; governments should be afraid of their people. After all, what better way to remember remember the fifth of November than with a rewatch of this classic film.

Since Disneyland opened 70 years ago, fans have flocked to Disney Parks around the world. But around the year 2000, the Walt Disney Company decided to start bringing its beloved attractions to life on the silver screen for fans to experience outside of the parks. Surprisingly, they found one of their biggest franchises when "Pirates of the Caribbean: The Curse of the Black Pearl" hit theaters in the summer of 2003. 

Despite the ride being a beloved piece of Disney Parks lore, expectations were low for Gore Verbinski's pirate project starring Johnny Depp, Orlando Bloom, and Keira Knightley. But after racking up plenty of acclaim by becoming the fourth-highest-grossing film of that year, fans were ready to join Captain Jack Sparrow's crew. So how does the House of Mouse top this unexpected treasure of a franchise? By delivering not only one of the best chapters of the series to date, but a technical marvel that still stands up to modern advancements in computer-generated effects.

In "Pirates of the Caribbean: Dead Man's Chest," Depp's now-iconic Sparrow finds himself hunted by the mythical Kraken due to an unpaid debt he owes to the legendary pirate Davy Jones. But as Jack attempts to find the titular chest to gain control over the Flying Dutchman and its gnarly squid/crab/pirate hybrid of a captain, a number of other parties also seek this treasure to serve their own purposes.

This swashbuckling sequel has so much to offer. With Captain Jack's rum-fueled antics, the family drama of Will and Elizabeth, and the phenomenal performance of Bill Nighy as the terrifying Davy Jones alongside his cursed crew of creatures, there are plenty of reasons to set sail for a rewatch every now and again.

When it comes to rewatching movies, viewers will often go back to revisit their favorites and relive the emotions they felt during their first watch. But sometimes a film can be so entrancing that it would warrant multiple viewings just to retrace the steps for a closer look at how things ended up where they did. One filmmaker who has become an expert at crafting films like this is Christopher Nolan. From "Memento" to "Inception" to even "The Dark Knight" trilogy, the director has his own signature way of unravelling a deeply psychological plot with plenty of twists, turns, and misdirection. One of his films where it's absolutely paramount to the story that he nails misdirection happens to be the one about magic.

"The Prestige" is a sci-fi thriller starring Hugh Jackman and Christian Bale as Robert Angier and Alfred Borden, magicians in Victorian London who become bitter rivals as they each try to perfect a teleportation trick in order to one-up the other. The two men become so obsessed with their rivalry that the feud results in a larger-than-usual body count for an occupation that is steeped in illusion.

A magician typically doesn't reveal how they execute their act. But Nolan's viewers have the ability to rewatch this incredible film to see exactly how things come together. Just as Angier and Borden challenge each other, the viewers are challenged by all the unsuspecting twists and turns of "The Prestige." It's definitely one of those great films where you pick up something new each time it's revisited. And due to dazzling performances from Jackman and Bale (plus a great appearance by David Bowie as Nikola Tesla), it's very easy to press play over and over again.

Before "Rick and Morty," "Bob's Burgers," or "Family Guy" rose to prominence, adult animation pioneer Mike Judge was changing the game with "Beavis and Butt-Head" and "King of the Hill." But despite being best known for his animated work, Judge still had his fair share of live-action hits, including HBO series "Silicon Valley" and cult classic film "Office Space." Although, his third film "Idiocracy" may stand as one of the best works on his resume.

The sci-fi satire follows Luke Wilson and Maya Rudolph as mild-mannered librarian Joe and sex worker Rita as they enter a government program to be guinea pigs for a suspended animation experiment. However, the program is ultimately forgotten and the duo end up being revived 500 years into a future where the average intelligence of the general public has greatly decreased. This leads to a crumbling societal infrastructure, vapid media output, and rampant consumerism. Now essentially the smartest man in America, average Joe sets out on a journey to find a time machine and return himself and Rita to their own time before succumbing to the stupidity of society.

Like "V For Vendetta," modern audiences (especially Americans) can unfortunately draw parallels between "Idiocracy" and reality. But rather than the doom and gloom of the Vertigo Comics adaptation, Judge's film has a bit more hope for the future, even though it was uncertain whether the movie itself would even have a future. After testing poorly, receiving a limited theatrical release in only seven cities with no promotion, and being abandoned on home video relatively quickly, it endured and achieved cult classic status like "Office Space." Now, hopefully a 20th anniversary rewatch will help US citizens find a positive light at the end of the dystopian tunnel they currently find themselves in.

Throughout the 2000s and 2010s, Clive Owen solidified himself as a bona fide leading man in Hollywood after gaining acclaim in his native England. And a crowning jewel of his filmography came in 2006 when he joined forces with Alfonso Cuarón for "Children of Men."

The visionary filmmaker behind "Harry Potter and the Prisoner of Azkaban," "Gravity," and "Roma" directed and co-wrote this dystopian action film based on the 1992 novel of the same name from P.D. James. Set in the not-too-distant future of 2027, the movie introduces a world where civilization is on the brink of collapse because humans have been unable to reproduce for two decades. But when cynical civil servant Theo Faron is tapped to aid a refugee escape the totalitarian government of the United Kingdom and find asylum. But when Theo learns that he's transporting the only known pregnant woman in the world, the stakes are raised considerably higher.

"Children of Men" just works on so many levels. There's adrenaline-fueled action, gorgeous cinematography with incredible technical innovation, and an ultimately optimistic outlook despite signs of a bleak future. Cuarón and company deliver one of 2006's best films that absolutely earns a place on any rewatch list

Will Ferrell cemented his legacy as a comedy superstar throughout the late 1990s and early 2000s. After his stint on "Saturday Night Live," he went on to star in several movies that defined comedy in the 2000s. You couldn't go anywhere at that time without hearing people quote his characters from "Zoolander," "Old School," "Anchorman," or "Wedding Crashers." "Elf" has become as synonymous with the Christmas season as Rankin and Bass stop motion animation. In 2006, the actor delivered yet another crowd-pleasing hit with "Talladega Nights: The Ballad of Ricky Bobby." But as rewatchable as that movie is, the offering from Ferrell's extensive filmography that made our list is actually "Stranger Than Fiction."

Directed by Marc Foster ("Quantum of Solace") from a script written by Zach Helm ("Mr. Magorium's Wonder Emporium"), this surreal dramedy tells the story of IRS auditor Harold Crick as he starts hearing a disembodied voice narrate his life – including the fact that he will die soon. Understandably, Harold is freaked out by this notion and starts spinning out (something that Ferrell does very well). But rather than going completely off the rails like he usually does in his movies, he shows restraint by demonstrating his dramatic chops just as fellow comedy icons Steve Martin and Robin Williams did before him.

In addition to the excellent performance from Ferrell in "Stranger Than Fiction," Harold is surrounded by a wonderful cast of characters played by legends in their own right, including Dustin Hoffman, Emma Thompson, Tony Hale, and Queen Latifah. And though these players can certainly handle the whimsical farce that many thought they would be getting here, the final product is an incredibly clever, intimate, and sweet film that deserves to be rewatched just as much as the star's other work. 

James Bond entered an all-new era when Daniel Craig stepped into 007's shoes for "Casino Royale." Following the trend of taking pop culture icons and looking at them through a more gritty and realistic lens (like "Batman Begins" or "King Kong"), we see Craig's Bond as a newly minted 00 agent with a fresh license to kill. In his first big mission, he targets Mads Mikkelsen's terrorist financier Le Chiffre as he enters a high-stakes poker game in order to take down the entire operation.

While a controversial choice at first, many will choose "Casino Royale" as the best James Bond movie. Though Craig portrays a more vulnerable and less experienced Bond, he still resonates with an audience who is more used to Jason Bourne or Ethan Hunt. His version of the character was praised as a throwback to Sean Connery and Timothy Dalton, while also evoking more of Ian Fleming's original character from the novel. Fans also appreciated filmmaker Martin Campbell's use of practical stunts versus the CG effects favored in prior installments of the series. All this was reflected at the box office as "Casino Royale" became the highest-grossing James Bond film until 2012's "Skyfall" premiered. 

With Amazon MGM Studios preparing to turn the page on this chapter of Bond with producers Amy Pascal and David Heyman, now is probably a good time to revisit the iconic character and his most recent escapades before it all begins again.

The practice of staying at a stranger's house instead of a hotel or motel seems commonplace these days. But back in 2006, Airbnb was largely foreign to the general public. Although, one thing that may or may not have eased people into the idea could be the beloved Nancy Meyers romantic comedy "The Holiday."

Kate Winslet and Cameron Diaz star as Iris Simpkins and Amanda Woods, two women who are fed up with love and are looking for a bit of an escape from their lives. Luckily, they connect through a website that offers them each an exciting getaway by exchanging homes. As Amanda heads to a quaint English cottage and Iris hops off the plane at LAX to explore sunny California, they each find love literally knocking at their doors when they least expect it.

Like many of Meyers' other works, "The Holiday" is cozy like a warm blanket during a snowy night. The plot may be somewhat predictable, but elements of the film are so charming that some shortcomings can be overlooked. First, Jack Black is such an incredible romantic lead that it's a shame that he didn't get many other roles like this one in his career. The scene where Iris and Miles are perusing Blockbuster is still legendary though. And second, Hans Zimmer really went hard with the score on this one. No one was expecting him to bring out the big guns for a holiday rom-com, but he came out guns blazing with the sweeping orchestration of "Maestro." As a result, this film has become an integral part of the winter holiday movie viewing.