The 17 Best 2000s Movies To Watch When You're Feeling Nostalgic

Y2K trends have monopolized just about every corner of the market, from a fashion renaissance to early aughts-inspired music. Even pop culture news has become inundated with references and reunions from the 2000s (Hi, Bennifer!). Nostalgic for better days, just about everything has become oversaturated with the ideals from the decade of boy bands, Destiny's Child, and Canadian tuxedos (á la Britney and Justin).

It was also the era of the cheesy romantic comedy — you know, the kind we watched during middle school sleepovers. The 2000s gifted us with some of the best (and worst) chick flicks that have since become iconic classics that will live on collecting dust on our old VHS stands — don't worry, they're also available on streaming platforms now. And given our obsession with everything else from that decade, it only makes sense for us to binge high-definition versions of all our old favorites.

So, in order to quench the thirst for everything early 2000s, we've rounded up the best 17 movies from the era that has completely taken over society with its recent resurgence. Read on for movie night recs starring young Jennifer Lopez, Ben Affleck, Kate Hudson, Matthew McConaughey, Reese Witherspoon, and more.

Gigli

The movie that started it all. While its 6% Rotten Tomatoes score may deter you, we love this oldie filled with palpable chemistry between a young Jennifer Lopez and Ben Affleck.

How to Lose a Guy in 10 Days

Andie Anderson (Kate Hudson) is a rambunctious reporter in New York City who is given the totally unrealistic assignment of finding a guy and getting him to dump her in 10 days. When an equally as charming and suave executive Ben Berry with an agenda of his own becomes her target, the task at hand proves to be a bit difficult.

Just Friends

Who in their right mind would say no to Ryan Reynolds? Long before he was trolling his wife Blake Lively on the internet, the actor starred in this hilarious comedy that sneaks in the important lesson to never judge a book by its cover.

The Princess Diaries

This early aughts staple had its 20th birthday last summer. If that doesn't make you feel old, an 18-year-old Anne Hathaway and 16-year-old (!!) Mandy Moore will. Alexa, play "Stupid Cupid."

Miss Congeniality

A classic masterpiece for the ages. But let's just all agree to never change for a man, OK?

Little Miss Sunshine

A dysfunctional family sets off for a road trip heading for the Little Miss Sunshine contest, where the youngest member of the family, Olive (Abigail Breslin), is competing.

Step Up

This movie is responsible for so many things: Channing Tatum's global stardom, and, in turn, Magic Mike; Jenna Dewan and Tatum's 10-year-marriage; and my short-lived middle school dance career.

Hitch

Relationship guru and dating coach Hitch (Will Smith) promises to help Albert (Kevin James) win over the girl of his dreams. But when Hitch begins to catch feelings for reporter Sara (Eva Mendes), he finds that his old tricks won't do.

Legally Blonde

Elle Woods (Reese Witherspoon) attends Harvard Law School to win back her ex-boyfriend Warner (Matthew Davis) — what, like it's hard? And while she may be studying law, she learns a slew of valuable lessons that are worth far more: push yourself to your fullest potential, never settle, and never let someone dull your shine.

A Walk to Remember

Your stereotypical popular jock falls for nerdy nice girl flick with a heart-rending twist. Grab the tissues.

Sisterhood of the Traveling Pants

Four best friends who have to spend their first summer apart come across a pair of jeans that magically fits them all perfectly. They decide to share and send the denim across the globe during their time away from each other. Blake Lively, America Ferrera, Alexis Bledel, and Amber Tamblyn star in the film based off the best-selling novel of the same name by Ann Brashares.

Pirates of the Caribbean

A deranged pirate named Captain Jack Sparrow (Johnny Depp) sets out on a ploy to seek revenge against his old crew and break a haunted curse. Plus, Orlando Bloom and Kiera Knightly's insatiable sexual tension? Yo ho, yo ho, a pirates life for me.

John Tucker Must Die

Finally some vengeance for a privileged, womanizing male teenager. When high school hotshot John Tucker triple-crosses three girls, they join forces to seek revenge and bring down the jock.

The Ugly Truth

TV producer Abby Richter (Katherine Heigl) is struggling in the romance department, so her new on-screen talent, Mike Chadway (Gerard Butler), asserts himself as her guide to dating, until the two head-butting co-workers start to develop feelings for each other. Although, some of Mike's comments probably should have been reported to HR, just sayin'.

Lost in Translation

Two Americans feeling lost in Japan cross paths and form an unexpected friendship. Scarlett Johansson and Bill Murray star in this Oscar-winning film.

Walk the Line

Reese Witherspoon and Joaquin Phoenix star in the film based off the love story of country music phenomenon Johnny Cash and singer June Carter.

The Devil Wears Prada

This 2006 film captured the not-so-glamorous life of a hustling editorial assistant working in New York City during the golden era of magazines. Oh, and Meryl Streep's portrayal of the devilish Miranda Priestly? Groundbreaking.