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The Ultimate List of Unmatched 90s to 00s Flicks

Pop Culture

August 10, 2022

Chick flicks are enjoyed by so many because they are “feel-good” movies filled with dialogue and relationships. Some are lighthearted and funny, like 10 Things I Hate About You, while others are deep and emotional, like The Fault in Our Stars, but they all make you feel enlightened in the end.

Anyone can walk away from these films filled with positivity, new ideas about relationships, or even new thoughts on life. The whole point of chick flicks is to give you an escape from your everyday life and let you feel good. And here is a list of some of our favorites!

1. 10 Things I Hate About You (1999)

Loosely based on Shakespeare's infamously misogynistic play, The Taming of the Shrew, TTIHAY is a modern remake featuring Kat, a strong-headed and outspoken girl who finds dating a massive waste of time. This creates a tribulation in her younger sister, Bianca's life, who can only step into the dating world once her sister does.

Enter Cameron, a new student at the siblings' high school, who falls madly in love with Bianca and employs the mysterious Patrick Verona to woo Kat. What could possibly go wrong, right?

“Romantic? Hemingway? He was an abusive, alcoholic misogynist who squandered half of his life hanging around Picasso trying to nail his leftovers.”

2. Fools Rush In (1997)

After a chance meeting in Las Vegas and a night together at his place, young American construction supervisor Alex Whitman leaves Mexican photographer Isabel Fuentes pregnant. She finds him a few months later just to let him know what happened. In the rush of the moment, he follows her and they decide to get married.

A clash of customs and ideas ensues in their families and relationships because of their different cultural and national backgrounds, causing all-around mayhem.

“You will never know love unless you surrender to it."

3. Wake Up Sid! (2009)

In Mumbai, Sid Mehra is, in the words of his father, an arrogant, spoiled brat. He lives with a doting mother, subservient brother, and a father who pays for his credit card bills. He takes his college finals and then starts work at his father's business, lasting less than a week before walking out.

At a graduation party, however, he meets Aisha, newly arrived from Calcutta and set on becoming a writer. He shows her the city and helps her refurbish a rented flat.

A spark lights between them and he asks her if she'd like to progress from friend to something more, but she says no— he lacks ambition and isn't her type. Will her words, his exam results, a confrontation with his parents, and a break with his friends be enough to wake Sid up?

“Goals paane ki khushi tabhi mehsoos hoti hai … Jab usse kisi ke saath share kar sako.”

Translation: You feel the true bliss of achieving your goals when you have someone to share it with.

4. Erin Brockovich (2000)

Julia Roberts stars in this legal drama based on the story of a woman who helped win the largest settlement ever paid in a direct-action lawsuit. Erin Brockovich (Roberts) is a single mother of three who, after losing a personal injury lawsuit, asks her lawyer, Ed Masry (Albert Finney), if he can help her find a job.

Ed gives her work as a file clerk in his office, and she runs across some information on a little-known case filed against Pacific Gas and Electric. Erin begins digging into the particulars of the case, convinced that the facts simply don't add up, and persuades Ed to allow her to do further research; in time, she discovers a systematic cover-up of the industrial poisoning of a city's water supply, which threatens the health of the entire community.

"It was pretty intense, seeing somebody's first word, you know. All the words they'll say in their life and that's the first word she says, 'ball'. She just pointed her finger, with her beautiful soft chubby little arm, and her cheeks, and she was looking at it like she'd been looking at it for nine months y'know, and just couldn't get it out."

5. Sleepless in Seattle (1993)

Aching to experience a great romance in the likes of her new favourite film, An Affair to Remember (1957), the Baltimore Sun reporter, Annie Reed, keeps telling herself that her relationship and the imminent marriage to her frail fiancé, Walter, is the best thing that could happen to her. On the other side of the country, in Seattle--tired of seeing his father still reeling from the untimely loss of his wife--the precocious eight-year-old son of a widowed parent, Sam Baldwin, takes matters into his own hands, and calls a late-night radio talk-show, concerned about his insomniac and still single dad.

Now--among thousands of ecstatic and protective women across America--Annie feels an insuppressible need to meet in person the pained stranger with the lovely voice, starting to question her feelings for Walter. Are the Sleepless in Seattle and the Uncertain from Baltimore meant to be together?

“I'm gonna get out of bed every morning … breathe in and out all day long. Then after a while, I won't have to remind myself to get out of bed every morning and breathe in and out. And then after a while, I won't have to think about how I had it great and perfect for a while.”

6. Bride Wars (2009)

Since childhood, when they were only wide-eyed little girls, best friends Emma and Liv have been planning their magnificent future weddings down to the last detail. Patiently, sharing the same dream of having a June wedding at New York City's idyllic Plaza Hotel for almost twenty years, the girls will finally see their fantasy come true; however, when both nuptials are inadvertently scheduled for the same day, a full-scale war will break out. They say all is fair in love and war, but can a single mistake turn the once dear BFFs into best rivals forever?

"Sometimes in life there really are bonds formed that can never be broken. Sometimes you really can find that one person who will stand by you no matter what. Maybe you will find it in a spouse and celebrate it with your dream wedding. But there's also the chance that the one person you can count on for a lifetime, the one person who knows you sometimes better than you know yourself, is the same person who's been standing beside you all along."

7. What A Girl Wants (2003)

Daphne Reynolds (Amanda Bynes), a free-spirited American seventeen-year-old raised by her equally free-spirited mother, Libby Reynolds (Kelly Preston), goes to England to establish a relationship with her father, Lord Henry Dashwood (Colin Firth), who turns out to be a prominent political figure heavily involved in social customs.

Daphne must attempt to fit in with the social requirements demanded of her, while also getting to know her father, dealing with his other territorial daughter, and maintaining her own sense of identity.

"No hugging, dear. I'm British. We only show affection to dogs and horses."

8. Just My Luck (2006)

In Manhattan, Ashley Albright is a lucky woman and very successful in the agency where she works. The clumsy Jake Hardin is an unlucky aspirant manager of the rock band McFly, who is unsuccessfully trying to contact the entrepreneur Damon Phillips to promote his band.

When Ashley meets Jake at a masquerade party, they kiss each other, unbeknownst to the other's identities, swapping her fortune with his bad luck. She is horrified as her life upturns (for the worse) and causes mayhem around New York City, trying to find the mysterious man who has her luck.

“Everyone has bad days. You have to make the good ones.”

9. Notting Hill (1999)

Every man's dream comes true for William Thacker, an unsuccessful Notting Hill bookstore owner, when Anna Scott, a world-famous American actress, enters his shop. Soon after, William runs into her again, this time spilling orange juice all over her. Anna accepts his offer to change in his nearby apartment and thanks him with a kiss, which seems to surprise her even more than him.

Eventually, the two get to know each other better over the months, but friends affected with naivety and the all-devouring press ensure that being with the world's most wanted woman is far from an easy feat.

"It was sort of sweet actually—I mean, I know she's an actress and all that, so she can deliver a line—but she said that she might be as famous as can be, but also...that she was just a girl, standing in front of a boy, asking him to love her."

10. Sixteen Candles (1984)

On the pivotal morning of her sweet sixteen, bright-eyed high school sophomore, Samantha comes to realize that her family has completely forgotten her birthday. With her older sister's wedding ceremony only hours away, Samantha has to summon up the courage to pursue the handsome boy of her dreams, Jake; fend off the persistent freshman who has a crush on her, Ted the Geek; and, hopefully, find love. Will Jake ever notice her? Will Samantha blow her sixteen candles and make her wish come true?

“That's why they call them crushes. If they were easy, they'd call 'em something else.”

I hope you found some old-but-gold movies, as well as some newer recommendations, for your next movie night!

Ashna Aggarwal
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Writer since May, 2022 · 5 published articles

Ashna is a senior in high school with a penchant for studying, reading and binge watching old F1 races. The hour before it starts raining is her favourite weather and she likes all things caffeine. Outside of the things she's good at, she likes to paint and dance.