Fans still can’t get enough of 10 Things I Hate About You 23 years after its debut. This movie, which stars Heath Ledger and Julia Stiles, is a classic rom-com that is still at the top of everyone’s list of favorites. In the film 10 Things, two sisters who couldn’t be more dissimilar are featured: Kat (Stiles) and Bianca (Larisa Oleynik). Patrick (Ledger), who is hired to date Kat so that Bianca might date in accordance with their father’s regulations, woos her despite the fact that she is uninterested in the male gaze and is instead focused on her future. Kat and Patrick are diametrically opposed to one another, but it works. There is a powerful exhibition of love in the form of a solo bleacher performance, a heartbreaking love confession poem, and lots of ’90s feel-good feelings.
A Knight’s Tale offers another Heath Ledger dance routine if you’re in need of one. Ledger plays William Thatcher in this comedy set in the Middle Ages, a guy who attends jousting contests pretending to be a nobleman rather than a peasant. However, he naturally meets wealthy Jocelyn (Shannyn Sossamon) and starts to fall in love. Will Jocelyn still love him if she finds out who he really is? is the unanswered question. The late Ledger adds so much charm and demonstrates his talent once more for playing the romantic protagonist.
Can’t Hardly Wait
With its plot centered around a year-end party where Preston (Ethan Embry) only has one more chance to confess his feelings for Amanda (Jennifer Love Hewitt), this movie evokes the same nostalgia for teenage hangouts that 10 Things does. This film meticulously follows each of Preston’s decisions and acts as they attempt to conclude the year on a positive note with the help of all of his friends. You’ll relive the highs and lows of high school with the group, and there will be times when you’ll be both laughing and sighing simultaneously.
Clueless
Clueless is arguably one of the most quotable romantic comedies from the 1990s. Cher (Alicia Silverstone), a popular girl, is followed in this movie as she experiences the ups and downs of high school. She helps many of her friends find partners, makeovers, fashion, and the voice of reason, but it seems she has trouble finding love herself. When will Cher’s turn come? Viewers of this film will notice that the lead characters are in love with each other before they do, in yet another example of how opposites attract. This movie perfectly captures the nostalgia of high school in the 1990s and the early 2000s, and it has an excellent ensemble led by Paul Rudd, Brittany Murphy, and Stacey Dash.
Cruel Intentions
Cruel Intentions addresses entitlement, sexual conquest, and an unlikely change in character from a few of the kids who don’t seem to be redeemable in another movie where the popular kids utilize the geeks and goody two-shoes as players in their game. Stepsister Kathryn (Sarah Michelle Gellar) places a bet with Sebastian (Ryan Phillippe) that he can persuade Annette (Reese Witherspoon) to violate her abstinence vow for him. Sebastian wants Annette to fall in love with him, but by the end of the movie, he has definitely gotten more than he bargained for. This one is a classic, and the ensemble delivers such flawless performances that you can’t help but feel joyful, sad, and enraged for each character.
Drive Me Crazy
Melissa This frequently disregarded rom-com about two childhood friends who use each other to make their crushes and ex-lovers jealous stars Joan Hart and Adrian Grenier as Nicole and Chase. What began as animosity and fighting between Nicole and Chase transforms into a gentle romance and a steady falling in love as they spend more time together. The name of this movie, “Drive Me Crazy,” was inspired by a song by Britney Spears. It has another great music. Due to the abundance of romance comedies in the late 1990s and early 2000s, this film frequently is overlooked on lists where it should be included.
Easy A
The character Olive (Emma Stone) lies about losing her virginity in Easy A, one of the more recent movies on this list, which draws influence from the novel The Scarlet Letter. Olive resolves to proudly wear a “A” and act like a wicked girl as the lie keeps becoming worse and crazier. Olive now has to figure out how to get rid of the negative image and regain the good reputation she once had as she begins to get closer to her crush, Todd (Penn Badgley). This was Emma Stone’s breakthrough performance, and it is hilariously witty throughout.
Never Been Kissed
Although there isn’t a dating bet in this movie, there are some incredible makeover transformations, lies, and fond memories of high school. Josie Geller, played by Drew Barrymore, is a news reporter who poses as a high school student to gain inside information for a story she wants to write. Josie, who was the unpopular girl in high school, seizes the opportunity to prove herself and become a popular girl. The lone blip? It’s not exactly acceptable to act like a high school student while falling in love with your English teacher. You’ll laugh, swoon, and perhaps even shed a few tears as you watch Josie change and gain confidence throughout the course of the film. Additionally, the music and attire are distinctly ’90s.
She’s All That
Freddie Prinze Jr., a 1990s heartthrob, plays Zack Siler, a popular athlete at his school, in the movie She’s All That with Rachael Leigh Cook. Taylor, a popular girl, and his picture-perfect relationship come to an end when she publicly dumps him in favor of someone else. He is betting that he can’t make the nerdy girl the prom queen in an effort to regain his confidence. Typical romantic comedy maneuver from the 1990s. He does transform the nerdy girl, Laney Boggs (Rachael Leigh Cook), but he also develops feelings for her. She’s All That, which follows a similar format to 10 Things with the Bet, with an all-star cast (Matthew Lillard, Paul Walker), and a compelling tale of how opposites meet.
She’s The Man
Soccer prodigy Viola (Amanda Bynes) poses as her brother Sebastian in order to play on a team made up exclusively of boys. There’s just one hitch: Duke (Channing Tatum), her roommate, who thinks she’s a boy, begins to fall in love with her. Even worse, Duke wants Viola to introduce him to a woman who shares the same feelings for Viola as Sebastian! She’s The Man, a comedy based on Twelfth Night by Shakespeare, is entertaining from beginning to end and features fantastic chemistry between Bynes and Tatum.
The Proposal
Sandra Bullock, who is amazing, plays Margaret Tate, a brilliant book editor whose work visa has expired and who is threatened with deportation in the movie The Proposal. Margaret persuades her assistant Andrew (Ryan Reynolds) to marry her in order for both of them to keep their jobs in order to keep their clientele and possibly their jobs. Together, the unusual couple—who can’t tolerate each other—explore Andrew’s home state of Alaska in an effort to figure out how to get married without the lie being discovered. This movie will make you laugh out loud the entire time and features some outstanding performances from the late Betty White and Mary Steenburgen.
