20 of the Best 2000s Movies to Watch for Instant Nostalgia
You Can Count On Me (2000)
Director Kenneth Lonergan’s work, whether on the screen or the stage, always punches you in the gut. In You Can Count on Me, Sammy (Laura Linney) and Terry (Mark Ruffalo) have lost touch, despite sharing the same grief of losing their parents in a car accident when they were children. Sammy is the responsible sibling, a single mom who works at a bank and remains in their hometown, while Terry has batted around and spent time in jail. When he needs money, he comes back into Sammy’s life, upending things and developing a close relationship with Sammy’s son (Rory Culkin).
The Devil Wears Prada (2006)
If you ever questioned the cultural relevance of The Devil Wears Prada, you can now look at pretty much any entertainment site and see rabid coverage of the upcoming sequel’s costumes, predictions for the plot, and updates on who will be making cameos. The interest isn’t surprising: Anne Hathaway, Meryl Streep, and Emily Blunt gave wonderful performances in the original movie. But it also shows that the themes of the film—which is essentially about getting a prestigious job, working yourself into the ground to keep it, and then realizing that none of it is worth it—might really resonate with people.
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Bend It Like Beckham (2002)
Bend It Like Beckham inspired a generation of young girls with its sportiness, the friendship between Jess (Parminder Nagra) and Jules (Keira Knightley), and a very relatable premise. (Jess’s traditional parents don’t want her involved in sports, and Jules has a controlling mother.) Plus, there are many queer undertones that make it that much more fun.
Love & Basketball (2000)
One of the most romantic sports movies of all time, Gina Prince-Bythewood’s Love & Basketball, her debut film, remains a favorite. Monica (Sanaa Lathan) and Quincy (Omar Epps) are childhood friends who both love basketball. The film is broken up into quarters that show the pair as young kids, then as high school students who fall in love, then as college athletes, and later playing basketball professionally. Few can forget the famous one-on-one scene.
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Kill Bill : Vol. 1 (2003)
Quentin Tarantino’s Kill Bill: Volume 1, a cult-favorite martial arts movie with more than a bit of violence, follows a character called the Bride (Uma Thurman) who was attacked by assassins on the day of her wedding. The assault, led by the Bride’s former boyfriend, kills all the wedding guests and the Bride’s unborn child. When she wakes up from a coma after four years, she’s hell-bent on revenge.
Almost Famous (2000)
Nothing better articulates the excitement of music fandom and youthful awakening as Almost Famous. Set in 1973, 15-year-old William (Patrick Fugit) is invited to shadow a rising rock band on tour and write about it for Rolling Stone. It’s a teenager’s wildest dream come true and the fact that it’s based on director Cameron Crowe’s own life is almost impossible to believe.
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Ocean’s Eleven (2001)
The fun that the actors had on the Ocean’s Eleven set has almost become more of a story than the film itself. It’s one of those remakes that makes you forget there was ever an original version. The 11-person gang, which intends to rob a casino, is a truly impressive assemblage of intergenerational actors, including George Clooney, Matt Damon, Brad Pitt, Elliott Gould, Bernie Mac, Don Cheadle, and Carl Reiner. Even Julia Roberts dazzles in her relatively small role.
Before Sunset (2004)
Nine years after spending a beautiful night together in Vienna in Before Sunrise, Jesse and Celine meet again. Jesse has written a book about his time with Celine and she attends a Paris reading. They wander around Paris, talking. They’re in their 30s now, and their lives are very different. Jesse is a married father and Celine has a successful career and boyfriend. Like Sunrise, Sunset is filled with deep conversations, beautiful scenery, and romantic simplicity that’s hard to beat.
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Training Day (2001)
Denzel Washington and Ethan Hawke are at their best as a pair of LAPD officers. Alonzo (Washington) is the grizzled veteran narcotics officer, while Jake (Hawke) is a junior officer. After one day together, Alonzo will judge whether Jake is allowed to join the narcotics division. It’s quite a day. There’s PCP smoking on the job, stealing from drug dealers, and intense corruption. Washington plays his tough, manipulative, and wily character to perfection, and Eva Mendes and Dr. Dre are great additions to the cast.
Michael Clayton (2007)
When people talk about the ways the movie industry has declined, they’re often referring to the lack of middle-budget films aimed at adults, with incredible scripts and great casts. Michael Clayton is a shining example of that category. Michael (George Clooney) is a fixer for a powerful law firm and is brought in when Arthur Edens (Tom Wilkinson), the lead attorney on a serious class action suit against an agricultural company accused of poisoning people, has a manic break. Clayton is asked to get Edens under control and, in doing so, is pulled deeply into a conspiracy. It’s a new classic and one of George Clooney’s best performances.
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Lost in Translation (2003)
Lost in Translation was the moment when I fell in love with Sofia Coppola. Set nearly entirely in a high-end Tokyo Hotel, it shows the blooming friendship between an actor in his 50s (Bill Murray) and a newly married young woman (Scarlett Johansson), both lonely and dissatisfied with their lives. The gorgeous shots of Tokyo are unforgettable, and Coppola’s lens makes every scene beautiful.
The Royal Tenenbaums (2001)
It’s one of Wes Anderson’s most beloved movies and probably the only one that inspires Halloween costumes year after year. The Tenenbaums, who rotate through a sprawling Harlem house with more identifiably Wes Anderson objects than you can imagine, include the patriarch Royal O’Reilly Tenenbaum (Gene Hackman), his ex-wife Etheline (Anjelica Huston), and children Chas (Ben Stiller), Richie (Luke Wilson), and Margot (Gwyneth Paltrow). The family dynamics are bizarre, funny, and sad, which makes for an unforgettable movie.
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Gone Baby Gone (2007)
For me, Gone Baby Gone sits alongside The Sixth Sense and Gone Girl (the book) as the plot twists that shocked me most. It’s a Boston-set neo-noir where two private detectives (played by Michelle Monaghan and Casey Affleck) are hired to search for a young girl who has disappeared. The fractures in the girl’s family are quickly made apparent by Amy Ryan in an amazing, against-type performance as the girl’s mother. The story is heartbreaking and has more nuance in looking at crime, child neglect, and moral ambiguity than most crime thrillers.
Brokeback Mountain (2005)
Brokeback Mountain transformed the understanding of who gets to make a Western. It was directed by Ang Lee, who made his first films in his native Taiwan, and was based on a short story by Annie Proulx, a writer who lived most of her life on the East Coast. But it was also co-written by Larry McMurtry, who wrote Lonesome Dove and other Western classics. At the time, it was relatively rare to see major movies with gay leads. It was also unusual for two straight men to be playing those parts, and Jake Gyllenhaal and Heath Ledger’s gripping performances hopefully pushed queer representation a bit farther.
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Eternal Sunshine of the Spotless Mind (2004)
After Joel (Jim Carrey) and Clementine (Kate Winslet) break up, they are both devastated. Clementine undergoes a procedure that wipes her mind clean of any memories of Joel. When Joel learns that’s possible, he also gets the procedure. Writer Charlie Kaufman created a strange but romantic story, and director Michel Gondry created a distinctive look and depth that made Eternal Sunshine so unforgettable.
The Dark Knight (2008)
For many, The Dark Knight is the greatest superhero movie. It’s unusually contemplative. Unlike many adaptations of comics, it places Batman (Christian Bale) in a darkness that seemed to reflect its moment in time. It tapped into the Bush-era disillusionment and seemed to reference the despair of post-9/11 New York. That Heath Ledger died only months before the movie’s release makes his take on the Joker all the more haunting.
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Y Tu Mamá También (2001)
Tenoch (Diego Luna) and Julio (Gael García Bernal), teenage best friends, find themselves on a road trip from Mexico City to Oaxaca with a beautiful, significantly older woman (Maribel Verdú). Y Tu Mamá También was groundbreaking, both in Mexico, where it was made, and in the U.S. It’s quite sexually explicit, but it also has a nuanced look at masculinity, which was rare for the era.
High Fidelity (2000)
John Cusack has never been more charming than he is here, playing Rob, a music obsessive who just doesn’t understand why his relationships with women fail. He and his record shop co-workers, who include Jack Black in a breakout role, help him make a Top 5 Worst Breakups list. Rob revisits each of the women, who range from a middle school kiss to a college girlfriend who sent him into depression, to figure out what he’s done wrong. The songs in the movie are excellent, and it also features a rare Bruce Springsteen cameo.
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City of God (2002)
Set in Rio de Janeiro, City of God is a devastating story of how lives that start in the same place can diverge in incredible ways. Boys growing up in the slums of the city are exposed to terrible violence, poverty, and gang activity. Rocket grows up in the ‘60s wanting to be a photographer. That dream fuels his motivation to move out of the slums, as many of the boys he grew up alongside become involved with gangs. As an adult, his photography captures the dramatically different directions young lives can take.
Best in Show (2000)
Truly one of the funniest movies ever, Best in Show is able to depict dog show participants in a way that’s so cutting that it’s hilarious to those of us who don’t really know what the “dog show person personality” is. Jennifer Coolidge, Jane Lynch, Parker Posey, Catherine O’Hara, and Eugene Levy play some of the most ridiculous characters of their careers and much of the dialogue is actually improvized.
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