‘90s vs 2000s Iconic Movies Showdown: Our Favorites To Binge This Weekend

Since we're feeling particularly nostalgic lately with the resurgence of Y2K trends, we have gathered a list of our top must-see films from each decade and we're putting them to the ultimate test.

No matter what generation you’re from, the movies from the ‘90s and 2000s are worth watching. Both decades are filled with some iconic flicks of a variety of genres, so no matter what you like, there’s definitely something on this list of our favorites for you and whoever else joins you for movie night!

The ‘90s are considered to be a particularly great era for movies, some of which helped to fuel the current fascination with ‘90s fashion. These movies will fulfill your nostalgia cravings and are worth watching a second (or third or fourth) time. But just like the ‘90s, the 2000s are filled with cult classics from all sorts of different genres that many of us reference (or quote line-by-line) to this day.

Settle in for what could prove to be our most controversial article to date. Let's get started.

Never Been Kissed vs Love Actually

The New York Times’ review of Never Been Kissed when it came out in 1999 was, well, unkind. But if you want our opinion, the reviewer got it wrong, as Never Been Kissed has stood the test of time and was even recently poorly emulated in Senior Year, starring Rebel Wilson. This rom-com starring Drew Barrymore tells the story of a 25-year-old, former nerd, who masquerades as a high school student. It will have you feeling nostalgic for the classic teen movies of years’ past, and luckily we’ve got lots more where that came from on this list. 

Christmastime or not, Love Actually is a classic rom-com worth the watch. It follows several different storylines that somehow all beautifully fit together in a way the viewer can follow. We're sure you won’t regret any of the 135 minutes of this film because to us, this movie is perfect...well, except for the romanticized infidelity.  

Our winner: Never Been Kissed (for every month except December)

My Best Friend’s Wedding vs 500 Days of Summer

If you haven’t seen My Best Friend's Wedding, you need to. Anything with Julia Roberts and Dermot Mulroney is pretty much an automatic hit, but this movie is truly something special. It will have you laughing, and as surprising as it may be in a romantic comedy, guessing what happens next. Will the childhood best friends end up together, or will Michael go on to marry Kimberly Wallace (Cameron Diaz)? Trust us, a few minutes in and you’ll want to know the answer, and you’ll have a lot of fun watching the journey to get there. 

This romantic comedy stars Zooey Deschanel as Summer, who dumps her boyfriend after exactly 500 days together. Her ex-boyfriend Tomp (Joseph Gordon-Levitt) is then forced to examine what went wrong. It's a sweet movie that will pull at your heart strings.

Our winner: My Best Friend's Wedding

Get a Clue vs Cadet Kelly

Lindsay Lohan in the '90s? Count us in. Lexy is a spoiled rich girl who is always hunting down the best stories for her school's gossip column. In a strange twist, one of her teachers goes missing and her friends decide to team together and investigate the alleged crime. The movie is full of teenage angst, adventure, and action.

While Lindsay is certainly adorable in Get a Clue, Hilary Duff will forever steal our hearts and her role in Cadet Kelly is no exception. Kelly's new stepfather enrolls her in the George Washington Military School where she struggles to adjust to her new role as a cadet while facing harsh criticism from her commanding officer, Jennifer. She nearly drops out...that is until she falls for a classmate and decides instead to embrace the lifestyle and join the drill team.

Our winner: Cadet Kelly

Notting Hill vs The Notebook

Julia Roberts strikes again in the rom-com classic Notting Hill, although let's get real, we’re all really watching this movie for Hugh Grant. Hello, he can do no wrong. Julia Roberts plays a movie star who, while traveling, quite literally runs into Hugh Grant, leading to some unfortunate, or perhaps not so unfortunate, spilled orange juice.

The Notebook has pretty much become the official romance movie for when you just need to have a good cry. Whether you’ve been dumped, did the dumping, or are in a happy relationship, this movie is worth the entire 2 hours. However, it's worth noting that this movie is basically centered around romanticizing infidelity in the name of true love. If you can get past that, it's a cute pick for sure.

Our winner: Notting Hill

There’s Something About Mary vs The Princess Diaries

When a movie warrants articles looking back on it 20 years later, you know something special has been created. Cameron Diaz is the girl next door in There's Something About Mary, and every guy’s dream. This hilarious flick follows men as they battle for her affection.

Cue the moment every girl fell in love with Anne Hathaway. She begins the film as a quirky nerdy girl before learning the news that she's actually a princess and her mom has been hiding a very important letter from her all along. As heir to the crown in Genovia, Mia begins a journey to learn the royal ways – including a hilarious makeover scene that will go down in history.

Our winner: The Princess Diaries

Now and Then vs Mean Girls

Okay, one of these may be a silly, catty film while the other is sweet and nostalgic, but they are both classic coming-of-age friendship flicks nonetheless. In Now and Then, four lifelong friends reunite when one of them becomes pregnant and they reminisce on their innocent younger years together.

Fetch still may never happen, but the movie Mean Girls did, and aren’t we all glad? This cult classic full of quotable genius is one you’ll rewatch again and again. It stars a power trio of actresses – Lindsay Lohan, Rachel McAdams, and Amanda Seyfried – and has the genius of comedians Tina Fey and Amy Pohler behind it. This is always worth a watch, whether it’s your first or seventh time seeing the film.

Our winner: Mean Girls

Fight Club vs Kill Bill

Fight Club came out in the ‘90s, but, as the New Yorker asserts and your real-life experiences may confirm, “men still quote Fight Club, still discuss what the movie really means, and still dress like its characters for Halloween.” It’s safe to say that this movie about men bored with the mundaneness of the day-to-day hamster-wheel of American life who start a club where they fight other men in underground basements remains a classic – even if it did initially fail at the box office. 

Kill Bill stars supermodel Uma Thurman who plays an ex-bride. After she wakes up from a coma years after her ex-fiancé tried to murder her, she vows to go on a killing spree of everyone who had any part in the loss of her unborn child. This dark movie has a cult following for a reason. If action and crime movies are your style, this 2000s classic is for you.

Our winner: Fight Club

10 Things I Hate About You vs A Walk To Remember

10 Things I Hate About You is one of my personal favorites. This lovely rom-com stars Heath Ledger who is cast as a bad boy hired to date Julia Stile’s character, an angsty teenage girl who wants nothing to do with him. It’s funny, charming, and the kind of movie you’ll watch again and again – swooning every time regardless of how many times you’ve already seen it. 

Another movie that will undoubtedly make you cry your eyes out! Mandy Moore, the shy preacher's daughter with a secret, and Shane West, an aimless, jaded teen, fall in love in a powerful way in this coming-of-age story based on the bestselling book.

Our winner: 10 Things I Hate About You

Maid in Manhattan vs The Devil Wears Prada

Arguably one of Jennifer Lopez's best roles to date, in which she's a maid who unexpectedly finds herself pursued by a Senatorial candidate. He assumes that she is a socialite after stumbling upon her while she's trying on rich woman's extravagant dress.

Another personal favorite of mine, and a cult classic, The Devil Wears Prada will not disappoint. You’ll fall in love with ice queen Miranda Priestly who is the ruthless editor of Runway and is played by none other than Meryl Streep. It was nominated for multiple Oscars for a reason, and if you ask us, it should have won.

While these two movies may not be similar at a glance, they both showcase the differences in power when it comes to fame and riches, and you're rooting for both of the leads, hoping they won't lose themselves in the identity crisis that ensues.

Our winner: The Devil Wears Prada

The Wedding Singer vs School of Rock

The Wedding Singer stars Adam Sandler, who works as a wedding singer yet has sworn off love after being left at the altar. But when he meets Julia (Drew Barrymore), a future bride who needs his help with wedding planning, who knows how long that will last. Trust us, this one is worth a watch. 

In School of Rock, a guitarist in need of money poses as a long-term substitute teacher at a prestigious private elementary school. He gets his students to embrace their inner rock’n’roll, not by teaching, but by focusing on their preparation for the music competition they entered. This cult classic starring Jack Black also features Miranda Cosgrove, which is a bonus for those who will recognize her from iCarly, though she’s much younger here. 

Our winner: The Wedding Singer

Clueless vs Legally Blonde

Thought we would leave Clueless off the list? As if! From the often recreated ‘90s looks, to the clever screenwriting, to Cher’s character arc, this movie fully earns its spot on the list of the best movies of the 1990s. This is another we find ourselves rewatching over and over, and if you’ve seen it, you understand why.

Who wouldn’t love Reese Witherspoon’s character Elle Woods? She gets into Harvard (“What, like it’s hard?”) to be with the boyfriend who dumped her for not being serious enough. But in this excellent comedy, boy, does she prove him wrong. 

This showdown may have been the toughest on the list, but we can't help ourselves from feeling connected to Elle Woods and her iconic pink fashion.

Our winner: Legally Blonde

Liar Liar vs Anchorman

Anything with Jim Carrey is going to make you laugh out loud, and Liar Liar is no exception. It’s about a liar, Fletcher Rheede, whose lies catch up to him and ruin his relationships. But this expert liar finds he is only able to speak the truth on a very important day in court because of a wish made by his son, and of course, hilarious chaos ensues. 

Who doesn’t love Will Ferrell? To me, he can do no wrong, and that includes his role in Anchorman where he plays an anchorman who accidentally ruins his career over a feud with a new journalist brought on the show. Of course, he has a chance to possibly get it back, and trust us, you’ll laugh the whole time he tries. 

Another tough pick, but Liar Liar has such a sweet storyline that will remind you of what's truly important at the end of the day.

Our winner: Liar Liar

She’s All That vs Miss Congeniality

She’s All That is another rom-com classic that told an (admittedly cliché) story about a bet where Zack Siler (Freddie Prince, Jr.) could make Laney Boggs (Rachel Leigh Cook), the school’s nerd girl, into the prom queen. But cliché aside, the chemistry and charm of this movie make it a classic worth seeing.

How they made Sandra Bullock look so homely in the first part of this movie is beyond us, but she played this role so well. While it had the same concept of turning a "blah" girl into a gorgeous "10," Miss Congeniality at least had a bit more creativity with the plot as she was an FBI agent who went undercover in the Miss United States beauty pageant to prevent a terror group from bombing the event.

Our winner: Miss Congeniality

Closing Thoughts

The ‘90s and ‘2000s were both great decades for the film industry, filled with some movies we know you’ve seen (and should watch again) and some iconic ones that might have passed you by and are worth giving a go. 

Do you agree with our choice of the winner for each showdown? Comment and let us know your favorites!

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