The 2000s yielded some iconic films. The Lord of the Rings, Matrix, and Paranormal Activity franchises all trace their storied histories to the heady first decade of the new millennium. But you surely haven’t forgotten about these movies, nor have you forgotten about My Big Fat Greek Wedding, Avatar, or Batman Begins. All are streaming on Max, and none of them belong on this list.
This list is about the 2000s movies that, for one reason or another, haven’t stayed as fresh in our collective consciousness as, say, The Devil Wears Prada. Perhaps they were small budget movies that got overshadowed by the Star Wars prequels. Maybe they were middling movies you loved but never watched again, or they were award-winners you completely forgot once you leaped joyously into the 2010s. Whatever the case may be, each of the movies on this list is sure to spark joy when you remember that they exist and, hopefully, that they deserve a rewatch.
1. Heartbreakers
The romantic crime comedy is a highly underutilized movie subgenre. The stakes are high, the laughs are big, and the twists come with a kiss. It’s a winning combo, any way you slice it, and Heartbreakers is an archetypal triumph of the form.
Sigourney Weaver and Jennifer Love Hewitt are Max and Page, a mother-daughter con artist team who have to complete one last grift together to pay a debt to the IRS. But when Page develops feelings for a man she’s trying to con on the side (Jason Lee), their whole delicate web of lies is placed in jeopardy. Heartbreakers is a rom-com with an edge: it’s funny, it’s irreverent, and it’s unpredictable.
How to watch: Heartbreakers is now streaming on Max.
2. American Gangster
American Gangster is a smart, smooth crime thriller about the rise of 1970s heroin kingpin Frank Lucas. Denzel Washington commands the screen as Lucas, who used returning Vietnam War servicemen to smuggle drugs from Asia into the U.S. The product, Blue Magic, is so pure that it quickly dominates the markets and turns Lucas into Harlem's top crime lord. Across the river, Richie Roberts (Russell Crowe) is a Newark detective whose partner overdosed on Blue Magic, and he's been tasked with bringing Lucas’s sprawling heroin racket down.
Directed by Ridley Scott, American Gangster is enthralling, entertaining, and unforgettable. It takes the classic gangster flick and adds to it an intelligent conversation about class structure. But its most impressive features are the dynamic performances of its two arresting leads.
How to watch: American Gangster is now streaming on Max.
3. Sky Captain and the World of Tomorrow
Gwyneth Paltrow is Polly, a determined reporter in an incredible fedora who always gets her story. Jude Law is Joe, the head of an elite air force squadron, and also Polly’s ex. When enormous metal monsters attack New York City, the pair are thrown back together in a race to get to the bottom of the mystery and stop the doomsday device they fear is waiting for them there.
Taking inspiration from Old Hollywood science-fiction films, Sky Captain and the World of Tomorrow is a modern movie with a nostalgic, 1930s aesthetic. The technology seen in this fictional New York is both antique and futuristic — people travel by airships that dock at the Empire State building — a vision of the "future" as imagined by those in the past. The result is an exciting film noir/sci-fi adventure that lovingly evokes the romance of a bygone era.
How to watch: Sky Captain and the World of Tomorrow is now streaming on Max.
4. Jennifer’s Body
You can thank the internet for facilitating pop culture's reevaluation of numerous cult classics. But few were as overdue and as important as the critical reassessment of Jennifer's Body.
Directed by Karyn Kusama and written by Diablo Cody, this snarky story of a teen girl sacrificed to the devil by a rock band was largely maligned upon its release in 2009. Critics complained about its balance of comedy and horror, with many admitting they just didn't get it.
But in the wake of the #MeToo movement, female horror fans and filmmakers took to social media to reconsider the film's strongest elements — namely, its nuanced approach to addressing sexual trauma and playful presentation of queer characters in a horror context. You'll want to queue this one up just for Megan Fox's wickedly fun delivery of, "No, I'm killing boys."* — Alison Foreman, Entertainment Reporter
How to watch: Jennifer’s Body is now streaming on Max.
5. Walk the Line
Written and directed by James Mangold, Walk the Line is a hall-of-famer when it comes to movies about musicians.
This story of Johnny Cash’s ascent from Southern nobody to one of the greatest country singers of all time hits all the key beats of the classic biopic: traumatic childhood, stint in the army, shocking success, whirlwind romance, and eventual drug addiction. But that doesn’t make it any less worthy of a watch. Joaquin Phoenix is dark and captivating as the troubled crooner, singing all the performances himself to the shock of audiences who would have sworn it was Cash’s voice on the track. As June Cash, Reese Witherspoon burns up the screen with her energy, stealing every scene she’s in. She won a well-deserved Oscar for this unforgettable performance.
Watching Walk the Line is an engrossing, whole-body experience, from the toe-tapping tunes to the visceral emotions that drive these musical geniuses.
How to watch: Walk the Line is now streaming on Max.
6. I Love You, Man
The concept of a "bromance" began to seriously take root in the 2000s and was perhaps concretized by co-writer/director John Hamburg's I Love You, Man. This is not a romantic comedy, folks. It's a bro-mantic comedy.
Paul Rudd is Peter Klaven, a real estate agent whose recent engagement to the love of his life (Rashida Jones) makes him realize he doesn’t have a best man. Peter decides it’s time for another man in his life. At first it seems that crass, brazen Sydney (Jason Segel) is the opposite of what Peter is looking for, but he just might be what Peter needs after all. I Love You, Man is a sweet and bawdy romp about the discomfort of making new friends as an adult. Its greatest achievement, though, is Rudd and Segel’s sparkling chemistry — this was their third movie together, after Knocked Up and Forgetting Sarah Marshall.
How to watch: I Love You, Man is now streaming on Max.
7. Hustle & Flow
And now, the movie that garnered Three 6 Mafia an Academy Award for Best Original Song, Hustle & Flow. DJay is a Memphis pimp who yearns for a better life. He turns to music, calling in favors and putting it all on the line to record an album about the trauma of street life. His goal is to give his music to a big time rapper (played by Ludacris) at a hometown party on July 4th — will his tracks be ready in time?
Hustle & Flow, written and directed by Craig Brewer, is both wholesomely optimistic and unapologetically gritty. The world these characters navigate is cutthroat and criminal, but they always hold on to a spark of hope. Terrence Howard earned an Oscar nom for his layered performance as DJay, and the rest of the cast (which includes Anthony Anderson and Taraji P. Henson) are equally spellbinding
How to watch: Hustle & Flow is now streaming on Max.
8. Charlie Wilson's War
In 1980, Congressman Charlie Wilson (Tom Hanks) wasn’t doing much with his position besides throwing lavish parties. But prodding from a friend (Julia Roberts) pushes Wilson to take an interest in Afghanistan’s fight against the Soviet occupation. Written by Aaron Sorkin and directed by Mike Nichols, Charlie Wilson’s War is an exciting and chic take on diplomacy. It’s both an excellent vehicle for that Philip Seymour Hoffman swagger and a crash course on historical cause and effect. The events of this film directly shaped American foreign policy and engagement for years to come. A surprisingly jaunty movie about a serious moment in history whose ramifications were felt by the entire world.
How to watch: Charlie Wilson’s War is now streaming on Max.
9. (500) Days of Summer
Sometime in the 2000s, romantic comedies stopped trying to be funny and started trying to say something meaningful, none more overtly than (500) Days of Summer. This indie darling breaks from rom-com formula to tell a non-linear story of a relationship coming together and falling apart. Joseph Gordon-Levitt's sincerity is palpable and Zooey Deschanel, as the object of his affection, is a quirky girl so quirky she single-handedly ushered in a new era of messy bangs for millions of women everywhere. With unexpected touches of surrealism and a stellar supporting cast, (500) Days of Summer is a satisfying watch for a love story that hits you right in the gut.*
How to watch: (500) Days of Summer is now streaming on Max.
10. Real Women Have Curves
Real Women Have Curves, written by Josefina López, was the movie that gave us America Ferrera's big-screen debut, so for that alone we must pay our respects. But it’s also a stirring, nuanced, coming-of-age story about body positivity, the immigrant experience, and the struggle between what we owe our families and what we owe ourselves.
Ferrera is sensational as Ana Garcia, a Mexican American student who is finishing her senior year at a high school in Beverly Hills. While her fellow students head off to college, Ana stays behind, pushed by her mother to work and help to support the family. But Ana can’t help but dream bigger for herself, so while working in her family's factory, she begins to put together an application for Columbia University. A must-watch!
How to watch: Real Women Have Curves is now streaming on Max.
11. Pearl Harbor
Ben Affleck and Josh Hartnett are Rafe and Danny, 1940s air force pilots, lifelong best friends, and grade-A beefcakes. When Rafe’s plane goes down in the UK, Danny mourns alongside Rafe’s girlfriend, Evelyn (Kate Beckinsale), and their shared grief blossoms into a romance. But uh oh! Rafe miraculously returns — shocked and hurt to have escaped a POW camp to now find himself in a love triangle. Also, they were stationed at Pearl Harbor right before it was attacked. That’s a part of this, too.
Directed by Michael Bay, Pearl Harbor is a juicy melodrama that romanticizes war and glosses over minor details like "historical accuracy." Critics hated it. But honestly, who cares! We don’t need all of our movies to be good. We need some movies to be indulgently soapy fluff with absurdly high stakes and an impossibly hot cast — and Pearl Harbor is exactly that.
How to watch: Pearl Harbor is now streaming on Max.
12. Maria Full of Grace
María Álvarez is a pregnant 17-year-old in Colombia who becomes a drug mule in an effort to earn a better life for herself and her future child. Her pregnancy makes her the ideal smuggler, since it will keep her from being x-rayed. Maria Full of Grace is a truly sublime film, and a deeply human study of the modern drug-trafficking landscape. Catalina Sandino Moreno is exquisite and heartbreaking as Maria, her performance becoming even more impressive when you learn it was her first acting credit — and one that earned her a well-deserved Academy Award nomination.
How to watch: Maria Full of Grace is now streaming on Max.
13. Fantastic Mr. Fox
Adapted from the Roald Dahl children’s book by Noah Baumbach and Wes Anderson (who also directs), Fantastic Mr. Fox is a quirky and stylish stop-motion romp about a fox who just can’t quit thieving produce. When his criminal behavior puts his family in danger, Mr. Fox commits to a safer lifestyle, but years as a journalist can’t keep him yearning for his old life. He raids a local farm and catches the attention of three determined farmers who vow to take him out.
This movie is full of whimsy, giving animals a rich underground community that includes badger lawyers, opossum superintendents, and little fox kids who love juice boxes. As with all Anderson flicks, the visuals are gorgeous, and the cast is stacked. George Clooney lends his smooth voice to the titular sly fox, with Meryl Streep as Mrs. Fox, Willem Dafoe as a rat, Bill Murray as a badger — the list goes on and on.*
How to watch: Fantastic Mr. Fox is now streaming on Max.
14. Barbershop
Calvin Palmer Jr. (Ice Cube) is fed up managing his father’s old barbershop and sells it to a loan shark, freeing himself from the responsibility. But soon, Calvin regrets his decision and tries to buy back the property. Unfortunately, the loan shark wants double the original payment. Just as Calvin breaks the news to his friends and coworkers at the shop that it's about to close for good, one of his barbers is mistakenly arrested for a crime he didn’t commit, and the community has to rally together to free him. The entire movie takes place over the course of one transformative day in the barbershop itself, as newcomers pop in and out to move the plot along.
Barbershop is a warm comedy-drama that has spawned sequels, TV series, and spin-offs (Beauty Shop with Queen Latifah). It’s no wonder. The cast is magnetic (Anthony Anderson, Sean Patrick Thomas, Eve, Michael Ealy, Keith David, Cedric the Entertainer), the characters fresh and endearing, and the barbershop as vivid and vital as ever.
How to watch: Barbershop is now streaming on Max.
15. Gangs of New York
Martin Scorsese's Gangs of New York is the violent story of territorial gang warfare and revenge set against the backdrop of a 19th century New York City. Two rival gangs are fighting over the lower Manhattan neighborhood of Five Points: the Protestant Confederation of American Natives, led by Bill the Butcher (Daniel Day-Lewis), and the Dead Rabbits, led by "Priest" Vallon (Liam Neeson). Bill wins by murdering Vallon, but his triumph — such as it is — doesn't last forever. Years later, Vallon’s son (Leonardo DiCaprio) returns to Five Points to infiltrate Bill’s inner circle and avenge his fallen father.
Based on Herbert Asbury's book of the same name, Gangs of New York is a visual feast, with eye-catching costumes and astounding production design. Though like many Scorsese flicks, some critics thought the level of violence was a bit gratuitous, all agreed that Gangs is an exhilarating and gripping American epic.
How to watch: Gangs of New York is now streaming on Max.
16. The Water Horse
Angus MacMorrow is a young boy living in WWII-era, coastal Scotland who is both drawn to the water and deathly afraid of it. He spends his time collecting shells from tide pools and counting the days to his father’s return from the war. But one morning he finds a mysterious egg on the shore of the nearby loch. It hatches into a cuddly and ravenous baby Loch Ness monster (the titular "water horse") that he must keep hidden from his mother, as well as the regiment of British soldiers billeting in his house while searching for German submarines.
The Water Horse is a fantastical and heartwarming family adventure about both friendship and grief. A perfectly pleasant watch for family movie night, starring Emily Watson, Alex Etel, Ben Chaplin, David Morrissey, and Brian Cox.*
How to watch: The Water Horse is now streaming on Max.
17. The King’s Speech
There aren’t a lot of movies about the royals that leave you feeling uplifted, which is why Tom Hooper’s superb The King’s Speech is such a rare treat. Colin Firth is Prince Albert, or Bertie, the second son of King George V, whose public speaking engagements are commonly derailed by his stammer. Bertie’s wife (Helena Bonham Carter) pushes him to see unconventional therapist Lionel Logue, played magnificently by Geoffrey Rush. When Bertie’s older brother King Edward VIII (Guy Pearce) abdicates the throne, passing the crown unexpectedly to Bertie, the pressure for success becomes even higher, while Logue’s eccentric techniques come under closer scrutiny.
The King’s Speech is a captivating and effervescent historical drama, both playful and moving. It was, no surprise, an Academy Awards smash, winning Best Picture, Best Director, Best Actor for Colin Firth, and Best Original Screenplay for David Seidler.
How to watch: The King’s Speech is now streaming on Max.
18. Eastern Promises
Nothing says holiday cheer like Viggo Mortensen as a Russian gangster casually blow-drying a frozen corpse in front of a strand of Christmas lights. Eastern Promises doesn’t have anything to do with the holidays directly, but it is set during Christmas in London, where the atmosphere of hope and celebration is juxtaposed with violence and deceit.
David Cronenberg’s violent crime drama follows Naomi Watts as a midwife who discovers the diary of a young Russian girl who died in childbirth. That diary leads her to the local headquarters of the Russian mafia, and a dark scheme led by top boss Semyon (Armin Mueller-Stahl), his loose-cannon son (Vincent Cassel), and their newest recruit and fixer Nikolai (an excellent Mortensen covered in faux Russian prison tattoos). A suspenseful and gory mystery unfolds as Watts's Anna gets closer to the truth, and Nikolai balances carrying out his boss's orders with helping her. Morality and corruption constantly bleed into one another in Cronenberg’s fantastic crime fable, which features an all-timer nude fight sequence in a bathhouse.
How to watch: Eastern Promises is now streaming on Max.
19. Die Another Day
Pierce Brosnan’s last turn as James Bond marks the end of an era. A few months after Die Another Day hit theaters in 2002, The Bourne Identity premiered, ushering in a new generation of more grounded and grittier action films, subsequent Bond installments with Daniel Craig included.
Die Another Day is not gritty. It’s suave, smooth, and a little bit campy. The stunts are big and the explosions are even bigger — but its brazen improbability is its strength. This is an escapist action flick. It opens with James Bond surfing into North Korea, blowing up a war camp, and then getting tortured for 14 months while Madonna sings “Die Another Day” in the background. And that’s where the movie starts! This classic Bond flick is ludicrous and amazing. It’s as cool and breezy as action can be, and it only gets more fun when an iconic Halle Berry joins the mission.
How to watch: Die Another Day is now streaming on Max.
20. Definitely, Maybe
A surprisingly heartfelt Ryan Reynolds stars as Will Hayes, a young dad in NYC attempting to explain to his daughter Maya (Abigail Breslin) why he and her mother are divorcing. She insists on knowing the full story, so he starts from the very beginning, changing the names so the identity of her mother is a mystery, How I Met Your Mother-style. As the story unfurls, and Will grows closer and drifts apart from characters played by Elizabeth Banks, Isla Fisher, and Rachel Weisz, Maya begins to deduce which woman is her mother… and which woman is the love of her father’s life.
Definitely, Maybe is an enchanting and unique love story that confidently breaks out of the rom-com formula. With a talented cast and a cheerful tone, it was a breath of fresh air in an oversaturated decade for romantic comedies.
How to watch: Definitely, Maybe is now streaming on Max.
21. The Sum of All Fears
A bomb goes off in a Baltimore stadium and all signs point to Russia. But is Russia to blame? Or is there another perpetrator trying to trigger a new world war so they can swoop in afterwards and claim the pieces for themselves? CIA analyst Jack Ryan might be the only one who can get to the truth.
Ben Affleck is cool and capable as a younger version of Tom Clancy’s famous Jack Ryan, a role previously filled by Alec Baldwin (The Hunt for Red October) and Harrison Ford (Patriot Games; Clear and Present Danger). While The Sum of All Fears doesn't quite live up to the sophistication of its predecessors, it’s still a slick, tense, and entertaining spy thriller. And it was facing an uphill battle: Fears debuted only a few months after 9/11, and it features violence on American soil. Now that plenty of years have passed, it’s time to give this riveting suspense a rewatch.
How to watch: The Sum of All Fears is now streaming on Max.
22. Speed Racer
Unfairly maligned upon release, the Wachowskis' live-action take on the 1960s manga and anime from Tatsuo Yoshida has gained cult status in the 15 years since it flopped in theaters. This kaleidoscopic creation begs to be beheld on the big screen, spinning and whirling and careening as it does with every candy color under the sun. If you've got a good set-up at home, you can’t go wrong watching the pop-saturated adventures of Speed (Emile Hirsch), Trixie (Christina Ricci), Pops and Mom (John Goodman and Susan Sarandon), and the whole gang as they rush us through a hallucinogenic wonderland of fast cars, thrilling races, and one adorable pet chimp. As usual with the Wachowskis, this movie was deeply ahead of its time and deserves total rediscovery. At least until I can see it again on a big screen as intended!* — Jason Adams, Entertainment Reporter
How to watch: Speed Racer is now streaming on Max.
23. Kate and Leopold
Hugh Jackman is at his most dashing as Leopold, a 19th century New Yorker who gets magically transported to 2001 thanks to an inconvenient time portal. There, he meets Kate (Meg Ryan), a cynical career woman who, of course, doesn’t really believe in love. Maybe an old-timey gentleman bursting with chivalry will be just the man to warm her frozen heart! Co-written by James Mangold (Girl, Interrupted; Walk the Line) and Steven Rogers (I, Tonya), Kate and Leopold is a swoon-worthy romance with a deeply charismatic cast.
How to watch: Kate and Leopold is now streaming on Max.
24. Milk
In director Gus Van Sant's astounding biopic, Sean Penn stars as activist and politician Harvey Milk. The first openly gay man to be elected to public office in California, Milk progressed the rights of LGBTQ Americans by unprecedented leaps and bounds. Milk honors that legacy with its heartfelt imagining of an icon. Penn won Best Actor for his portrayal of Milk at the 81st Academy Awards.* — A.F.
How to watch: Milk is now streaming on Max.
25. Robots
For a throwback watch that will entertain the kiddos, look no further than 2005’s Robots. Ewan McGregor, Robin Williams, Halle Berry, Mel Brooks, Jennifer Coolidge, Jim Broadbent, and more — we can’t list names forever! — star in this high-energy animated sci-fi adventure about, you guessed it, robots. Rodney Copperbottom (McGregor) is an idealistic young inventor who becomes a local hero when he uses his skills to repair damaged or outmoded robots. The company that was trying to sell upgrades to these busted robots at a major premium? Well, suffice it to say, they’re pissed. The movie’s strength comes from its imaginative depiction of a robotic world (its transportation system is basically a Rube Goldberg machine), making Robots an enchanting pick for family movie night.
How to Watch: Robots is now streaming on Max.
26. Constantine
Before he was John Wick but after he was Neo, Keanu Reeves was Constantine, an exorcist with both a bad attitude and the ability to see half-angels and half-demons living in secret as humans. Seems like the latter might have something to do with the former, huh? Based on the DC Comics series Hellblazer, Constantine is a dark fantasy thriller filled with religious iconography and superhero vibes. Rachel Weisz, Shia LaBeouf, Tilda Swinton, and Djimon Hounsou lend their prodigious talents to the film, with Swinton particularly in her element as an androgynous half-angel. Though the movie has suffered from the inevitable comparisons to the superior Matrix trilogy, Constantine is a solid watch for horror lovers and fantasy fans alike.
How to Watch: Constantine is now streaming on Max.
UPDATE: Jan. 3, 2024, 4:15 p.m. EST This list was updated to reflect the latest offerings on Max.
Topics Film HBO Watch Guides
