10 Greatest 2000s Movies Worth Watching Over and Over

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Leonardo DiCaprio as Frank Abegnale Jr lying on a bed holding a fake check in Catch Me If You Can

The 2000s were a great time for Hollywood. Something was definitely in the air back with producers were churning out one masterpiece after the other. I’m not talking about films that were great for their time, but stories that held universal appeal and were meant to feel just as great decades later as they did when they premiered.

I’m also not saying that the 2000s didn’t deliver some of the biggest cinematic disasters of all time. The point is, even those remain memorable, though, because this was a time when studios were willing to take risks, and the era of franchises hadn’t yet dawned upon us. That’s why so many films from the decade continue to outshine today’s releases. For anyone who’s still not convinced, here’s my list of the 10 greatest 2000s movies worth watching over and over again.

10 ‘Mamma Mia!’ (2008)

Christine Baranski, Meryl Streep and Julie Walters singing and dancing in Mamma Mia!

Mamma Mia! is a feel-good musical that you can just never have enough of. The film, directed by Phyllida Lloyd, is set on sun-drenched Greek Islands and understands escapism like no other. The plot is simple yet engaging enough to get invested in almost immediately. You have Sophie (Amanda Seyfried), a bride-to-be who secretly invites three men from her mother Donna’s (Meryl Streep) past to her wedding in the hopes of finally learning which one is her father. What makes the premise all the more special is how it’s built entirely along ABBA’s iconic discography, which allows Mamma Mia! to fully lean into its musicality.

This is a film that you have to watch with no questions asked, because the story’s refusal to take itself too seriously is the whole point. The brilliant ensemble cast, featuring Pierce Brosnan, Stellan Skarsgård, and Colin Firth, genuinely commits to the light-heartedness of the film while still punctuating it with hard-hitting moments. ABBA songs like “Slipping Through My Fingers” and “The Winner Takes It All” elevate the story’s emotional stakes and actually drive the story forward in meaningful ways. Above all else, though, you get the sense that the cast is genuinely having fun telling this story, and that is a feeling very few films can capture.

9 ‘Mean Girls’ (2004)

The Plastics pose at the end of their talent show Christmas Dance in Mean Girls (2004).

Mean Girls has stood the test of time and continues to define pop culture to this day. The film, written by Tina Fey and directed by Mark Waters, is the perfect high-school comedy that just about everyone can relate to. The story follows Lindsay Lohan as Cady Heron, a homeschooled teenager who attends a public high school for the first time in America. She immediately finds herself involved with the school’s trio of mean girls, led by the iconic but definitely evil Regina George (Rachel McAdams). The setup feels like your average teen drama, but soon enough, Mean Girls turns into a biting satire about the pressures of growing up and navigating social hierarchy. Obviously, the film is endlessly quotable with some of the most memorable jokes and one-liners of all time.

However, what makes Mean Girls so rewatchable is the film’s brutal honesty. The jokes land, but so do the messages behind them. As Cady becomes obsessed with popularity, her actual life starts falling apart, and this arc is what gives the film its weight. The script is smart without ever punching down or feeling out of touch with the actual struggles of being a teenager. Mean Girls might just be one of the most realistic depictions of the way high school cliques work, which is why it holds up as one of the strongest teen movies of all time.

8 ‘The Hangover’ (2009)

Hollywood went through a total reset when The Hangover first premiered. Male-centric comedy adventures can very easily lean into raunchy humor and poorly developed character arcs, but Todd Phillips took a very different direction with this one. The film follows pals Phil (Bradley Cooper), Stu (Ed Helms), and Alan (Zach Galifianakis) as they wake up in a trashed Las Vegas hotel suite with no memory of the night before, a baby in the closet, a tiger in the bathroom, and their best friend Doug (Justin Bartha) missing just days before his wedding. That sets the stage for pure chaos, and while that hooks you in, the film goes far beyond hilarious gags and shock value.

The Hangover turns the aftermath of a wild bachelor party into a mystery and forces the characters to piece together what happened. This structure gives the story its momentum and keeps the comedy rooted in something meaningful. The chemistry between the cast is easily the biggest selling point of The Hangover. Galifianakis’ Alan, in particular, became instantly iconic with how totally clueless the character is. This mix of character-driven comedy, sharp pacing, and absolute absurdity is what has earned The Hangover its lasting legacy. A lot of films from the 2000s have aged terribly, but The Hangover is one that you will want to keep going back to over and over again for these very reasons.

7 ‘Kill Bill: Volume 1’ (2003)

Uma Thurman as the bride, holding her katana defensively across her face in Kill Bill.

Quentin Tarantino really outdid himself with Kill Bill: Volume 1. The action thriller feels like an adrenaline rush with a no-holds-barred story about vengeance, memory, and survival. The film follows The Bride (Uma Thurman), a former assassin who wakes up from a four-year coma after being left to die and immediately begins crossing names off her kill list. Kill Bill: Volume 1 doesn’t even pretend to be subtle, but that’s part of its charm. You aren’t supposed to question the story’s exaggerated stakes because that ruins its purpose. This fearless commitment to absurdity is what makes the film hit with the same intensity every time you watch it.

Thurman completely dominates the screen, but Lucy Liu’s Ren serves as the perfect rival who holds her own. The House of Blue Leaves sequence remains a masterclass in pacing and visual storytelling, and is only one of the many reasons why Kill Bill: Volume 1 is a must-watch for anyone looking to immerse themselves in a completely unique experience. The film pays homage to spaghetti westerns, grindhouse cinema, and anime, and is one of Tarantino’s most ambitious works, but the way it all comes together is beautiful, fun, and heartbreaking at the same time.

6 ‘Avatar’ (2009)

Image via 20th Century Studios

James Cameron’s Avatar is a piece of art. The sci-fi epic practically redefined the genre with its larger-than-life worldbuilding, intense storytelling, and obsessive attention to detail. The story takes place on the hostile moon of Pandora and follows Jake Sully (Sam Worthington), a paraplegic former Marine who joins the Avatar Program after his brother’s death. Jake sees the mission as a second chance at purpose and mobility as he inhabits a genetically engineered Na’vi body, but soon enough, he finds himself deeply immersed in Na’avi culture and starts to fall in love with Neytiri (Zoe Saldana). This forces Jake to choose between the world he comes from and the one that finally feels like home to him. The conflict is obviously the heart of the film, but what makes Avatar special is how the film immerses its audience in the story.

Cameron spends his sweet time presenting Pandora as a fully-realized living system with its own rules, plants, animals, and ecosystems. The environment feels lived-in and almost sacred instead of coming across as sterile and digitally manufactured. This helps the audience view the Na’avi from a more empathetic lens. The film conveys strong messages about environmental preservation and the cost of colonialism, but they never feel too on-the-nose and are intertwined into the plot itself. Avatar gives its audience a world that feels fascinating and alive, and you rewatch the film to experience that spectacle all over again.

5 ‘The Royal Tenenbaums’ (2001)

The Royal Tenenbaums is not a film about good people doing good things, but that doesn’t make it any less entertaining. The story centers on Royal Tenenbaum (Gene Hackman), a disgraced lawyer and absentee father, who re-enters the lives of his estranged family by lying about being terminally ill. Ben Stiller, Gwyneth Paltrow, and Luke Wilson play the roles of his burnt-out children who return to confront the emotional consequences of their father’s indifference toward them. The premise is funny on the surface, but Wes Anderson quickly turns the film into a story about neglect and the damage parents can inflict on their children without ever realizing it. The director treats the film as a novel with a storybook structure that makes everything easy to follow.

The Tennenbaum house serves as a character with every room holding endless memories that have led up to the family’s gradual distancing. Hackman delivers the performance of a lifetime and turns Royal into a character who is selfish yet still endearing. The Royal Tenenbaums is packed with layers of meaning and has to be watched several times to be fully understood and appreciated. The film doesn’t leave its audience with a perfect happy ending, but it just goes to show that sometimes, humor can be found in sadness, too.

4 ‘Eternal Sunshine of the Spotless Mind’ (2004)

Jim Carrey behind the scenes of Eternal Sunshine of the Spotless Mind

Eternal Sunshine of the Spotless Mind rewatchable almost feels fitting, given that its plot revolves around people erasing their memories. Now, sci-fi romances are tricky to nail. Writers often focus on one of the two aspects while the other gets lost in the way, but this film, directed by Michel Gondry and written by Charlie Kaufman, strikes the perfect balance of wonder and heart. The story follows the shy and introverted Joel Barish (Jim Carrey), who learns that his ex-girlfriend Clementine (Kate Winslet) has chosen to erase all memories of their relationship.

This leads to Joel signing up for the same procedure, only to realize that he doesn’t actually want to forget any of it. The narrative structure of the film is interesting since we watch the central romance unravel in reverse. It feels disorienting initially, but then, things start to fall into place. You see just how destructive Joel and Clementine were toward each other, but as the story progresses, you see how and why they fell in love in the first place. Carrey and Winslet share an effortless chemistry that makes the buildup to the climax totally worth it. Each rewatch of this film makes you believe in the power of fate all over again and shows how even failures are worth remembering.

3 ‘Spirited Away’ (2001)

Chihiro standing among flowers and looking up in 'Spirited Away'.

It’s almost impossible to pick a favorite Studio Ghibli film, but Spirited Away stands in a league of its own. The film is a coming-of-age fantasy about ten-year-old Chihiro (Rumi Hiiragi), who stumbles into a spirit world after her parents are transformed into pigs. The fantastical setup paves the way for Hayao Miyazaki to create a whimsical universe that operates on dream logic. We follow Chihiro as she takes a job in a bathhouse for spirits run by the witch Yubaba (Mari Natsuki), which is where she learns to work and survive. Her unusual friendship with the mysterious spirit Haku (Miyu Irino) is the heart of the story. The film does a great job of letting the audience see all of this through Chihiro’s eyes.

You go through the same feelings of confusion, fear, and gradual understanding as the protagonist, and that’s exactly what the nature of the film demands. Visually, Spirited Away is nothing short of a masterpiece. Each frame is packed with hand-drawn detail, and Joe Hisaishi’s score is the cherry on top. The thematic depth of Spirited Away gives the film its rewatch value. However, the film is ultimately a story about a young, brave girl finding herself, and that’s what you want to tune in for again and again.

2 ‘American Psycho’ (2000)

Christian Bale as Patrick Bateman looking straight ahead in American Psycho

American Psycho appears to be yet another horror film about a wealthy New York banker who murders people for fun. However, that’s not the case at all, because the violence in the film is almost a distraction from the actual point. The story follows Patrick Bateman (Christian Bale), a man who lives an aggressively curated and controlled life. That’s why you really don’t see it coming when he starts committing acts of extreme violence. What’s even stranger, though, is that no one around him seems to notice or care about any of it. His coworkers keep mistaking him for other men who look like him, which is a sharp satire on how individuality no longer exists in the modern world. All that aside, the film deliberately keeps its audience in a state of confusion where you never really know what’s real.

This mirrors the disorientation that Bateman himself is going through, and turns the story into a horrific commentary on consumer culture. You slowly realize that Bateman isn’t killing because he enjoys it. Instead, he kills because he wants to be seen and feared by a society that only cares about surface-level perfection. Willem Dafoe grounds this convoluted narrative as private investigator Donald Kimball, along with Chloë Sevigny as Jean. The film’s most infamous moments, including Bateman’s monologues, only get better with time, because not only are they funny, they also expose how hollow the characters in American Psycho truly are. The horror in the film comes from the idea that we live in a society that doesn’t look beyond outward appearances, and that message continues to be relevant to this day.

1 ‘Catch Me If You Can’ (2002)

Tom Hanks sitting in a house and looking at someone off-camera in Catch Me If You Can.

Catch Me If You Can is one of Steven Spielberg's most brilliant character studies. The film follows Leonardo DiCaprio as a teenage runaway, Frank Abagnale Jr., who finds himself living a life of fraud. What starts as survival quickly becomes Frank’s personality as he slips into all kinds of roles to scam people out of money. The highlight of the film is Frank’s interesting dynamic with FBI agent Carl Hanratty (Tom Hanks), who becomes the only adult to constantly show up for him, even if it’s across an interrogation table. Their conversations strip away all pretense and reveal the hidden sadness that drives Frank’s need to keep changing appearances and always be on the run.

That’s when you start to notice how unfair life has been to Frank and how feeble his sense of self really is, with DiCaprio doing absolute justice to the protagonist’s internal conflict. By the time the story winds down, you aren’t really invested in the chase, because you see that Frank is just a troubled kid trying to escape his past. Catch Me If You Can balances charm with genuine heartbreak, and that’s what makes it one of Spielberg’s most realistic works.