10 Y2K Comfort Movies To Watch Before Prime Video's ‘Elle’
The countdown is on until Prime Video’s Elle (2026) premieres and introduces a new chapter of Elle Woods’s life before she went to law school. In the meantime, there are several Y2K movies to enjoy to get you in the spirit of the late ‘90s and early 2000s. Of course, there is some required viewing heading into the new show. There are also entirely unrelated movies that set the vibe, whether it be their appreciation of the color pink or their sense of humor.
A lot of these movies are often brushed aside as chick flicks. But movies made about and for women aren’t a bad thing. These movies have much more to offer than they often get credit for. They have endearing coming-of-age stories and heartwarming romances. They tackle universal themes and important subject matter, and they often do so through memorable characters and jokes that are still quoted today. The great news is that you can either stream these titles for free or rent them on Prime Video!
Elle Woods (Reese Witherspoon), to this day, still inspires me to give my entire life a makeover in a stylish montage because of Legally Blonde. This character changed the game; she challenged people’s perceptions and proved herself at Harvard without losing her sense of self. I appreciate that Legally Blonde took Elle and her ambitions and her interests seriously.
Still, the movie is fun as it embraces Elle’s charms with the “bend and snap” or her pink and scented resume. Legally Blonde also has an incredible supporting performance from Jennifer Coolidge. Personally, I don’t think I will ever get over the healthy, supportive romance between Elle and Emmett (Luke Wilson). There’s just not much I don’t love about Legally Blonde.
I know some people think that this sequel isn’t necessary because the original movie is that good, but I love it for what it is. I don’t think I ever expected it to match Legally Blonde because that movie feels so special and singular, but I really like catching up with Elle again. Legally Blonde 2: Red, White & Blonde doesn’t need to reinvent the wheel to be a worthy watch for me.
It’s hard to be too mad at Legally Blonde 2: Red, White & Blonde when it adds Sally Field, Regina King, and Bob Newhart to the movie’s universe. What a cast! Also, it makes total sense for Elle to be entirely against animal cruelty. Admittedly, I’m a sucker for Elle and Emmett’s romance, so I really love everything this sequel delivers with them after the original movie.
A Cinderella Story is one of my most formative movies. I can’t listen to Jimmy Eat World’s “Hear You Me” without thinking of Sam (Hilary Duff) and Austin Ames (Chad Michael Murray) kissing in the rain. I still think “Waiting for you is like waiting for rain in this drought, useless and disappointing” is one of the best mic-drop moments in a Y2K comfort movie.
There’s so much about this movie that I love, and this is coming from someone who also loves Another Cinderella Story (2008), starring Selena Gomez and Drew Seeley. It’s simply a magical, modern Cinderella retelling that always lifts my spirits. A Cinderella Story is a movie I’ve seen probably (and I’m not even joking) more than a hundred times, and I imagine I’ll watch it a hundred more. It’s well-cast, well-written, and it has a perfectly 2000s soundtrack.
It’s impossible to address Bring It On without acknowledging it as a total cultural phenomenon. Like so many other movies on this list, it became an instant Y2K classic. Its resonance reached well beyond that era, too, spawning an entire film franchise. It’s easy to see why. The cast’s chemistry makes the ensemble unforgettable. The writing is funny and perceptive. I can even recite the opening cheer from memory because one of my best friends taught it to me.
There is real spirit to Bring It On. It helps to have Kirsten Dunst, Gabrielle Union, and Eliza Dushku at the center of the competitive cheerleading world. With Peyton Reed behind the camera, there’s a real propulsive energy to the movie, too, that makes it watchable—and endlessly rewatchable. So much so, like many of the other movies on this list, I can basically quote the entire thing. No matter what, Bring It On will always be a go-to comfort movie.
I know that The Notebook is so many people’s favorite movie, let alone a romantic one. Sadly, this movie wrecked my heart in the same way as A Walk to Remember (2002), another Nicholas Sparks book adaptation. It’s one of those that I can’t watch, or I won’t be able to see through the tears. Sometimes, that’s exactly what you want in a movie, though. It also has so many moments that have become as quotable as they are unforgettable: “If you’re a bird, I’m a bird.”
This gorgeous yet heartbreaking movie hinges on the electric chemistry between Ryan Gosling and Rachel McAdams as Noah and Allie. There’s a reason they won Best Kiss at the 2005 MTV Movie Awards. I also believe that the movie laid the romance groundwork for James Marsden. He goes on to star in the charming Enchanted (2007), the brilliant 27 Dresses (2008), and another Sparks adaptation, The Best of Me (2014). For that, I’m eternally grateful to The Notebook.
As if we need any more evidence that Sigourney Weaver and Jennifer Love Hewitt have range, look no further than this romantic crime comedy. Heartbreakers transforms these Final Girls into brilliant con artists who charm wealthy men out of their money. Many movies, like The Hustle (2019), have tried to capture Heartbreakers’ essence with similar concepts.
Weaver and Love Hewitt are entirely enjoyable as this mother/daughter duo. The plot is a blast to watch, even if the runtime goes a bit too long. Also, this may be controversial for those who may gravitate to his heavier roles, but Heartbreakers is one of my favorite Ray Liotta movies. Fans of early 2000s movies certainly are missing out if they haven’t watched Heartbreakers.
Wimbledon is one of the most underrated romantic comedies from the early 2000s. I honestly think it could find an even bigger audience if it came out now. However, maybe that can still happen because sports romance is booming right now with Heated Rivalry (2025) and Off Campus (2026).
Paul Bettany plays Peter Colt, a professional tennis player who fears he may be past his peak. He stars opposite Kirsten Dunst as Lizzie Bradbury, a rising star in the women’s game. The movie explores how the high-pressure competition affects both players and their (initially) no-strings-attached romance differently. It’s also worth mentioning that James McAvoy delivers a wild supporting performance that I haven’t stopped thinking about since I first watched it.
Not only is it another excellent Lindsay Lohan movie from that era, but Mean Girls is also a Y2K touchstone. It’s one that I loved as someone who grew up in the early 2000s but appreciated in a whole new, creative way when I got older. That script, penned by Tina Fey, is absurd, hilarious, and entirely reflective of what it’s like in high school. Everything feels world-changing, and it especially is for Cady Heron (Lohan), who experiences going to a school for the first time.
There are so many universal themes at play in Mean Girls that the characters could become or stay archetypes. Instead, the movie pokes through the surface to find all these nuanced sides of iconic characters like Regina George (Rachel McAdams) and Karen Smith (Amanda Seyfried). Mean Girls is also likely the movie I quote the most from this list. Lines from this movie (“Get in loser, we’re going shopping”) are a part of my everyday vocabulary at this point. And the “On Wednesdays, we wear pink” of it all is very Elle Woods—from Elle to Legally Blonde.
I’ve seen Clueless so many times, and I don’t think I’ll ever get tired of it. With its take on Emma, it’s just one of the best modern Jane Austen retellings. I also don’t know that we would have all the other retellings of classic literature, like the truly incomparable She’s the Man (2006) and William Shakespeare’s Twelfth Night, without the success of Clueless.
So much of its appeal comes down to Amy Heckerling’s clever script. The movie wouldn’t be quotable without that magic on the page. Clueless’s cast is also excellent. Alicia Silverstone is perfectly cast as Cher Horowitz, a lead who constantly subverts stereotypes. Ultimately, I would classify Clueless and its unmistakable ‘90s Beverly Hills aesthetic as a must-see Y2K movie.
I’m not sure that I know how to write about 10 Things I Hate About You without being poetic about it. I’m sure it has flaws, but I really think that this movie is perfect. Heath Ledger as Patrick Verona set a bar so high for all other romantic leads, let alone those in Y2K comfort movies. If he’s not singing “Can’t Take My Eyes Off You” to win you back, is he even worth it? And Kat Stratford (Julia Stiles) is as cool as I want to be—always and forever.
This movie is clever, quick-witted, romantic, and a brilliant retelling of Shakespeare’s The Taming of the Shrew. I love 10 Things I Hate About You so much that I was nervous I wouldn’t like ABC Family’s adaptation in 10 Things I Hate About You (2009), but I did—for its similarities and differences. As it turns out, any spin on this story will always have my attention.
