The 2000s yielded some iconic films. Lord of the Rings, The Matrix, and the Ice Age franchise 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, Training Day, or Miss Congeniality. All are streaming on HBOMax, 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, I Am Legend. 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 would have been award-winners had they not premiered in the same year as Slumdog Millionaire. Whatever the case may be, each of the movies on this list is sure to spark joy as you remember that they exist and, hopefully, that they deserve a rewatch.
1. Matchstick Men (2003)
Nicolas Cage is a Los Angeles con artist whose life gets turned upside down when he finds out he has a 14-year-old daughter. Directed by Ridley Scott, this dark comedy is both funny and thoroughly absorbing. Sam Rockwell is an absolute gem (when is he not?) as Cage’s protégé, and Alison Lohman shines as Cage’s young daughter. Matchstick Men wholeheartedly deserves a rewatch and will certainly charm you as effortlessly as its characters do their marks. You know, there were a surprising amount of con-artist comedies in the early 2000s, including Heartbreakers, Catch Me If You Can, and Matchstick Men. Scamming regular people was obviously a much funnier concept before the 2007 housing market crash!
How to Watch: Matchstick Men is streaming on HBO Max.
2. The Town (2010)
Credit: Warner Bros / Kobal / Shutterstock
In 2010, Ben Affleck looked in the mirror and said, “I am going to make a Boston movie that is SO Boston.” Enter The Town, the Affleck-starring, -written, -directed, and -produced crime thriller about a group of Boston-born bank robbers planning to rob Boston’s Fenway Park, home of the Boston Red Sox. It may sound comical, but The Town is a surprisingly excellent film loved by critics and audiences alike. Part of its success comes from its impressive ensemble cast: Rebecca Hall, Jon Hamm, Jeremy Renner, Blake Lively, Titus Welliver, Pete Postlethwaite, and Chris Cooper, to name a few. Come for the iconic (and sometimes clichéd) Boston accents, but stay for the tense, well-written plot — your new favorite crime thriller awaits!
How to Watch: The Town is streaming on HBO Max.
3. Blue Crush (2002)
It’s the new millennium, baby! Women can surf now! This fluffy sports flick stars Kate Bosworth, Michelle Rodriguez, and Sanoe Lake as female surfers who clean hotel rooms during the day and surf Hawaii’s famous waves at night …even earlier in the day. Bosworth’s character was close to going pro until a harrowing accident halted her progress. Can she regain her confidence in time for an upcoming competition? There’s nothing new about the plot — you’ve seen this movie before — but the surf sequences are fresh and exhilarating. The movie feels like a breezy summer day: warm, bright, and fun. You might also squeal with delight when you see Bosworth’s love interest, Matthew Davis, who you’ll recognize exclusively as Warner Huntington III from Legally Blonde. But this time, he’s a good guy, we promise!
How to Watch: Blue Crush is streaming on HBO Max.
4. Changeling (2008)
For a meaty drama that hasn’t aged a day, look no further than Changeling, directed by Clint Eastwood and starring Angelina Jolie in an uncharacteristically delicate role. This poignant film tells the true story of Christine Collins, a woman in 1920s Los Angeles whose son has gone missing. When the LAPD announces they’ve found the boy, she claims they’ve brought back the wrong kid. Unfortunately, the LAPD disagrees. What follows is the heart-wrenching saga of a mother who will stop at nothing to get her son back, and the powerful forces conspiring to keep her quiet.
Changeling is absolutely astounding, in large part because the events that unfold — the gaslighting, sexism, and emotional abuse Collins endures — actually happened. Screenwriter J. Michael Straczynski meticulously included newspaper clippings and court documents with each scene of the screenplay. As a result, Changeling could legally be designated “a true story,” instead of “based on a true story” like so many other historical dramas. Stirring and unforgettable, with a magnetic performance from Jolie, Changeling is a must-watch whose themes still resonate today.
How to Watch: Changeling is streaming on HBO Max.
5. Romeo Must Die (2000)
Romeo Must Die is a kung fu/hip-hop adaptation of Romeo and Juliet starring Jet Li and Aaliyah. We’ll give you a moment to let that sink in. The 2000s were quite a time to be alive! Instead of feuding families, this insane and enthralling movie gives us warring Chinese American and African American gangs in Oakland, California. While the plot can get a bit slow, what we’re really here for are the astounding martial arts sequences paired with an electrifying hip-hop and R&B soundtrack. The juxtaposition, though fairly common now, was downright provocative at the time, cementing Jet Li’s performance as his breakout role for American audiences. Aaliyah also received praise for her work, which was both her acting debut and the only one of her films released in her lifetime.
How to Watch: Romeo Must Die is streaming on HBO Max.
6. The Brothers Grimm (2005)
Credit: Dimension / Miramax / Kobal / Shutterstock
Matt Damon and Heath Ledger in a middling adventure movie about 18th-century brothers battling supernatural forces? Yes, we’re interested, thank you! The Brothers Grimm positions the titular pair as traveling con artists (!) who perform fake exorcisms for cash — until they come across a very real, and very dangerous fairy tale curse. We cannot call this a good movie, per se, but we’ll happily label it a ridiculous and delightful watch. It’s the perfect encapsulation of early 2000s movie-making, when entertainment was in, deeper meaning was out, and Hollywood would make a movie about literally anything as long as a big name was attached. It’s a solid pick for those nights when you want to turn your brain off and watch something easy and fun. Keep your eye out for a pre-Game of Thrones, pre-fame Lena Headey!
How to Watch: The Brothers Grimm is streaming on HBO Max.
7. Volver (2006)
If you spent the 2000s watching entertaining fluff like the aforementioned Brothers Grimm, you probably weren’t paying attention to powerful foreign films. Let’s right that wrong, shall we? Written and directed by Pedro Almodóvar, Volver tells the story of a fierce family of women living just south of Madrid. A glowing Penélope Cruz anchors the group as Raimunda, a working-class mother who will do anything to protect her daughter, a girl secretly speaking with the ghost of her grandmother. Volver was hugely successful for an international title, garnering critical acclaim as well as BAFTA, Golden Globe, and Academy Award nominations. Both a comedy and a drama, this sincere and moving story will make you feel deeply and smile widely, a winning combination.
How to Watch: Volver is now streaming on HBO Max.
8. Robots (2005)
For a throwback watch that will entertain the kiddos, look no further than 2005’s Robots. Ewan McGregor, Robin Williams, Halle Berry, Stanley Tucci, Dianne Wiest, Mel Brooks, Jennifer Coolidge, Jim Broadbent, Amanda Bynes, 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 streaming on HBO Max.
9. Love and Basketball (2000)
When Gina Prince-Bythewood set about writing Love and Basketball, she claims she was aiming to create the Black When Harry Met Sally. What she built instead was an enormously successful cultural touchstone that has handily earned its own place in cinema history. Sanaa Lathan and Omar Epps are Monica and Quincy, lifelong neighbors, best friends, and basketball fans. The film follows their journey from childhood playmates to lovers to pro-ball players, each facing their own set of obstacles along the way. With powerful performances from its two leads, Love and Basketball is a confident and tender film. It is both a gripping sports drama and a compelling romance — a movie with something for everyone!
How to Watch: Love and Basketball is streaming on HBO Max.
10. Rat Race (2001)
Credit: Suzanne Tenner / Alphaville / Paramount / Seven Arts / Kobal / Shutterstock
Rat Race is a classic farce: Its premise is ridiculous, its jokes are outrageous, and it will likely elicit a few groans — but that doesn’t mean you won’t love it! Based on the ‘60s hit It’s a Mad, Mad, Mad, Mad World, Rat Race kicks off with an eccentric billionaire (John Cleese) challenging six teams of people to race from Las Vegas to Silver Springs, New Mexico in hopes of finding the $2 million he’s stashed there in a duffel bag. The ensemble cast here absolutely rises to the occasion, with Rowan Atkinson, Whoopi Goldberg, Cuba Gooding Jr., Wayne Knight, Jon Lovitz, Kathy Najimy, Breckin Meyer, Amy Smart, and Seth Green all fighting tooth and nail to be the first to reach the cash. It’s silly, it’s over-the-top, and a few of the bits are dated, but Rat Race was a beloved comedy in the 2000s — and it can still warm your heart some 20 years later.
How to Watch: Rat Race is streaming on HBO Max.
11. Constantine (2005)
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 streaming on HBO Max.
12. Insomnia (2002)
Remember that brief period when Robin Williams played against type by taking a few roles as the villain? Enter Insomnia, the Christopher Nolan psychological thriller which pits Al Pacino’s slowly-unraveling detective against Williams’ creepy killer. This riveting film is unpredictable and atmospheric, its foggy, Alaskan backdrop a reflection of the characters’ own moral ambiguity.
Receiving universal praise, Insomnia is the perfect pick for those nights when you want a movie you can really sink your teeth into.
How to Watch: Insomnia is streaming on HBO Max.
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13. Igby Goes Down (2002)
In the 2000s, most of us were too busy watching Lord of the Rings a thousand times to notice the indie comedy-drama Igby Goes Down. Kieran Culkin is Igby, a disillusioned teen who rebels against his old money, East Coast family and finds himself wrapped up in New York’s artsy underground scene. Claire Danes, Jeff Goldblum, Amanda Peet, Ryan Phillippe, Bill Pullman, and Jared Harris round out the cast, with Susan Sarandon, as Igby’s self-absorbed mother, giving a particularly memorable performance. If you missed this funny and touching film the first go around, don’t wait a second longer. You might also notice something as the film pans across the NYC skyline: Igby Goes Down is one of the last movies to show the World Trade Center towers intact.
How to Watch: Igby Goes Down is streaming on HBO Max.
14. Gigli (2003)
Let’s put our cards on the table: Gigli is an objectively terrible movie. Clumsy, confusing, and downright offensive, Gigli is widely considered to be one of the worst movies of all time. It has a 6% on Rotten Tomatoes. 6%!!! A year ago, we would never have even glanced at Gigli as a contender for this list, preferring it to fade into the ether like a bad nightmare, but unfortunately this is the movie where J.Lo and Ben Affleck met. And since we are living in the darkest timeline, and J.Lo and Ben Affleck’s recent reunion is the single shining light propelling us forward toward hope, this awful movie has suddenly become relevant again.
In Gigli, irritatingly pronounced JEE-lee, Affleck and Lopez team up to kidnap the brother of a federal prosecutor. But that’s not why you’d watch this movie! You’d watch this movie to see the very first Bennifer sparks twinkle mischievously into the universe. Alas — you might not even get that: Critics at the time complained about the lack of chemistry between the two leads! It’s truly astounding how bad this movie is! Watch Gigli, or don’t (maybe don’t), but we would not have been doing our journalistic duty if we hadn’t noted its current availability on HBOMax. You’re welcome, and also we’re sorry.
How to Watch: Gigli is streaming on HBO Max.