Top 10 Most Nostalgic 2000s Movies

Who knew that one of the best movies of the 2000s would have Jim Carrey playing a shy loner and Mark Ruffalo dancing in his underwear? This movie represents a very special time in early 2000s cinema when auteurs like Charlie Kaufman were taking major risks with their storytelling. “Eternal Sunshine” could have easily collapsed under the weight of its own ambition, but it holds together extraordinarily well. It also contained Jim Carrey and Kate Winslet at the height of their cultural powers, and Winslet’s character is a great representation of the manic pixie dream girl trope that permeated the 2000s. Her hair alone just screams nostalgia.

Maybe it’s cliché to say, but they just don’t make movies like “Bring It On” anymore. This is another example of those mid-budget teen movies aimed squarely at young females that permeated the late ‘90s and early 2000s. This movie just barely squeaked into the new millennium, and as such, it shares an atmosphere with the teen movies of the ‘90s. The soundtrack is rife with early 2000s classics, featuring bands like Atomic Kitten, P.Y.T., and even early 50 Cent. The cast is also very 2000s, featuring Gabrielle Union and a teenage Kirsten Dunst. It’s no coincidence that she is in both this and “Eternal Sunshine.” Is she the key to 2000s nostalgia?

A coming-of-age comedy for middle-aged men, “Sideways” is about a pair of unmoored friends taking a trip through California’s wine country. One is a failed writer and the other is an actor who is well past his prime. “Sideways” reminds us all of the mid-2000s, when smaller films like this could still make over $100 million at the box office - all while scoring multiple Oscar nominations. It also brings us back to the wine craze that followed the movie, specifically the drop in demand for merlot and the increased consumption of pinot noir. And finally, there’s a very mid-2000s aura about the main cast, including Paul Giamatti and Thomas Haden Church, both of whom were very popular at the time.

Visually, “Napoleon Dynamite” looks like a movie from the ‘80s. However, that is entirely by design. The movie is depicting a small town that is stuck in time, where its fashions, technology, and interior decorations are decades behind. But the movie is incredibly 2000s, and any kid who grew up in that decade is sure to have fond memories of it. The very presence of Jon Heder just screams 2000s. Many teens of the time are also bound to remember Vote for Pedro T-shirts and now-iconic lines like “Frickin’ idiot!” and “Your mom goes to college!” Actually, the entire movie is basically a meme at this point, and that’s because everyone has fond memories of its release and the immediate impact that it caused.

Many people have very fond memories of “Legally Blonde.” So much so that many attorneys, law students, and journalists have cited it as an inspiration in their lives. For them, this is probably the ultimate comfort movie. Of course, you don’t have to be a lawyer to have nostalgia for “Legally Blonde.” That’s generated through the soundtrack, which contains the likes of Black Eyed Peas and Vanessa Carlton. The mere presence of Reese Witherspoon, Luke Wilson, and Selma Blair in the same movie. The pink outfits, which were incredibly popular in sororities of the time. And even the mere look of the film, which straddles the line between ‘90s and 2000s. Watching this really takes us back.

The impact of “The 40-Year-Old Virgin” is still being felt today. While it has intelligence and a heart, most people remember “The 40-Year-Old Virgin” as the raunchy and improvisational movie that launched Judd Apatow’s career. He’s basically been making the same movie ever since. The film is also a glorious throwback to the mid 2000s. There are countless pieces of outdated technology in the store, like a combination DVD and VHS player. The characters play poker, as the card game was really hot at the time. Trish owns an eBay store. The guys play an old “Mortal Kombat” game at Andy’s. While still hilarious, “The 40-Year-Old Virgin” now serves as a nostalgic period piece.

We don’t know what’s more nostalgic - the general tone of the movie, the cars, or seeing young versions of all these popular actors. Let’s start with the cast. It’s very 2000s. Paul Walker was still an up-and-comer, Vin Diesel was a perfectly sculpted 30-something, and Michelle Rodriguez was barely out of her teens. There’s the campy “street” atmosphere of the film, which seems like a carry-over from the late ‘90s. And of course there are the cars. What seemed cool and state-of-the-art back in the early 2000s is quite laughable today, and it really tends to date the movie. Modern viewers may find it hard to get into, but those who saw it back in 2001 are sure to have fond memories.

This movie doesn’t seem as blatantly 2000s as “The 40-Year-Old Virgin.” That’s probably because it was actually written in the late ‘90s. And aside from a few pieces of then-modern tech, “Superbad” has a weirdly ambiguous setting. It seems more like the ‘90s than it does the mid-2000s. The nostalgia isn’t really found in the visuals, but in the cultural moment of the movie itself. “Superbad” was enormously popular, and it’s one of those movies that everyone remembers watching - especially teens. It also made major stars out of Jonah Hill, Michael Cera, and Christopher Mintz-Plasse. When someone thinks back to the first time they saw those actors, it usually filters down to “Superbad” and the mid 2000s.

Ask someone for one specific movie that defines the 2000s, and they’ll eventually get to “Mean Girls” (if it’s not their first answer, that is). Despite being one of a thousand teen movies, “Mean Girls” stood out. And it still stands out today, being one of the most memed movies in existence. Its popularity continues not because it’s a great movie, but because so many people have strong nostalgic links to it. For millions, this was the movie of their teenage years. It defined that specific time in their lives, and it spoke to them in ways that other teen movies didn’t. Watching “Mean Girls” is a time machine back to mid-2000s high school, and for many, that’s a very comfortable place to be.


Before we unveil our top pick, here are a few honorable mentions.

“Lost in Translation” (2003)
Nothing Says Early 2000s Like a Middle Aged Bill Murray & a Teenaged Scarlett Johansson



“Brokeback Mountain” (2005)
A Culturally Significant Movie That Also Happened to Be Robbed at the Oscars


“High School Musical” (2006)
This Is Still a Guilty Pleasure of All 2000s Teenagers


“The Devil Wears Prada” (2006)
A Movie That Defined the Mid-2000s & Kickstarted a National Interest in High Fashion

Where do we even start with “Borat?” It’s hard to imagine just how popular this movie was in 2006. You couldn’t go anywhere without hearing someone quoting one of the many hilarious lines, nor could you avoid the relentless Borat impersonations. It’s incredibly nostalgic from a pop culture perspective. However, it also works perfectly as a time capsule into mid 2000s America. Borat directly references the still-fresh 9/11, meets prominent politicians of the time like Bob Barr, talks about President Bush and the War on Terror, and brings iPods back to his village. Put simply, no other movie defines the 2000s quite like “Borat,” and it serves as the perfect vehicle for nostalgia. Is nice!