The 20 best high school rom-coms of all time

Get ready to feel old. The iconic '90s teen movie "She's All That" hit theaters two decades ago! In celebration of the film's 20th anniversary on Jan. 29, 2019, Wonderwall.com is running down our all-time favorite high school rom-coms, starting with "She's All That." The 1999 flick had it all: a beautiful dorky girl, a sensitive popular guy, a stupid bet, prom and all the drama in between. "She's All That," which starred Rachael Leigh Cook and Freddie Prinze Jr., reached No. 1 at the box office in its first week of release. Keep reading for more of the very best teen romance films…

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Our hearts melted when Heath Ledger serenaded Julia Stiles on the soccer field in "10 Things I Hate About You." The 1999 flick is the perfect high school romance movie with its witty one-liners, heartfelt poems, fantastic source material (Shakespeare's "The Taming of the Shrew") and all-star cast (Heath, Julia, Joseph Gordon-Levitt, Gabrielle Union). In fact, "10 Things I Hate About You" was so great that it opened at No. 2 at the box office during its first weekend behind only the blockbuster "The Matrix."

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A high school rom-com list without "Clueless"? As if! "Clueless" truly defined a generation. We lived for the sweet romance between Cher, played by the perfect Alicia Silverstone, and her ex-stepbrother Josh, played by an adorable Paul Rudd. Add the amazing wardrobes, fabulous teen life and iconic '90s language and "Clueless" is the perfect teen film.

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We love "Love, Simon" for taking the teen rom-com story and reviving it in the best way possible. The heartfelt films centers on a cute, popular guy (played by Nick Robinson) who comes to terms with his sexuality and finds love with a fellow male classmate. "Love, Simon" — the first film by a major Hollywood studio to focus on a gay teenage romance — grossed $66 million worldwide. It's funny, sweet and wonderfully acted — all the ingredients for flawless rom-com.

"Never Been Kissed" is a unique high school rom-com considering neither of its main characters are actually students. In the 1999 flick, 25-year-old reporter Josie, played by the lovable Drew Barrymore, returns to high school as an undercover student for a story. There, she meets and falls for her teacher, who's played by Michael Vartan. "Never Been Kissed" has an all-star cast (Drew, Michael, Molly Shannon, John C. Reilly, James Franco, Jessica Alba) and a super-cute story, all contributing to its $84 million in earnings.

Aw, "Sixteen Candles" — what many (including us) would consider to be the quintessential teen romance film. After a run of bad luck, nerdy sophomore Samantha, played by '80s teen queen Molly Ringwald, ultimately gets the perfect 16th birthday gift when she shares a kiss over a cake with her senior knight in shining armor, played by Michael Schoeffling. The 1984 movie, directed by John Hughes and co-starring Anthony Michael Hall, is a must-see for any rom-com fan.

Quincy McCall and Monica Wright might end up married by the end of "Love and Basketball," but their romance started years before while they were in high school. The 2000 movie about high school sweethearts has it all: the signature prom scene, funny '90s lingo and a "first time" moment that may be the sweetest in Hollywood. Starring a young Sanaa Lathan and Omar Epps, "Love & Basketball' is not to be missed.

We loved the sweet romance between cheerleader Megan Bloomfield (played by Natasha Lyonne) and her fellow conversion therapy attendee Graham Eaton (played by Clea DuVall) in 2000's "But I'm a Cheerleader." The teen satire follows Megan after her family sends her away to "cure" her lesbianism. There, she finds love with the charismatic Graham. "But I'm a Cheerleader" is unique, hilarious and endearing, all qualities that make it one of the best.

Sure, we all love Duchess Kate and Duchess Meghan, but Princess Mia Thermopolis is our hands-down favorite royal. In 2001's "The Princess Diaries," American high school student Mia not only finds out she's actually a European royal but finds love with her best friend's brother, fellow classmate Michael Moscovitz. The Disney teen movie, which grossed over $165 million, starred future A-listers Anne Hathaway and Mandy Moore and the legendary Julie Andrews. 10/10!

Get the tissues ready! "A Walk to Remember" might be the sweetest, saddest teen romance movie we've ever seen. The 2002 film follows Landon Carter and Jamie Sullivan as they fall in love and confront her battle with leukemia. We nearly ran out of tissues watching Landon kiss Jamie after her breathtaking performance in the high school play. Starring Mandy Moore in her breakout role and Shane West, "A Walk to Remember" is a true classic.

"Grease" really is the word, guys! The 1978 high school musical is legendary for its fabulous songs, perfect choreography and iconic love story. The movie follows greaser Danny Zuko, played by a young and super-attractive John Travolta, and Australian transfer student Sandy Olsson, played by a gorgeous Olivia Newton-John, as they navigate love and friendship. "Grease" might be over 40 years old, but it's just as amazing today as it was back then. Fun fact: The "Grease" soundtrack was the second-best selling album of the year in 1978.

What happens when you mix a classically trained ballet dancer and a med school-bound hip-hop kid from opposite worlds? True love, of course! Sara Johnson and Derek Reynolds' love takes center stage in 2001's "Save the Last Dance," in which they overcome different backgrounds, the death of a loved one, gang associations and teen angst. Julia Stiles and Sean Patrick Thomas shine in this teen-focused rom-com.

From its super-cute story to its legendary theme song, "Drive Me Crazy" is a blast across the board. The 1999 movie stars Melissa Joan Hart (a '90s icon) and Adrian Grenier (our childhood crush) as next-door neighbors who decide to fake-date each other to make their real crushes jealous. The twosome soon realize that they already have true love — with each other. "Drive Me Crazy" was a major hit, grossing over $22 million — plus it gave us one of Britney Spears' best songs!

"Say Anything" has a ton of moments that make it one of our favorite teen rom-coms of all time, but the most iconic has to be the boombox scene. The grand gesture we've all been waiting for IRL! After losing his girlfriend Diane, Lloyd Dobler plays "In Your Eyes" by Peter Gabriel outside of her window to show his love. Starring John Cusack and Ione Skye, "Say Anything" received rave reviews from critics and audiences when it opened in 1989.

"Dope" is definitely one of the dopest movies we've seen so far. The 2015 indie flick has a hilarious and heartfelt story, phenomenal acting and the perfect soundtrack, making it one of the best. "Dope" follows Malcolm Adekanbi, a geeky teen from Inglewood, California, who falls for Nakia, a cool and classy girl who's struggling to get her GED. Their sweet romance is complicated when Malcolm is forced to help out a drug dealer acquaintance. Shameik Moore and Zoe Kravitz excel in this feel-good film, which was produced by Forest Whitaker.

Our list wouldn't be complete without this John Hughes film! "Pretty in Pink" is the ultimate teen rom-com thanks to Brat Pack members Molly Ringwald and Andrew McCarthy and scene-stealer Jon Cryer. Molly stars as Andie, an artsy outcast who falls for Blane, her popular and rich classmate. Their relationship faces an uphill battle thanks to their different social statuses. Meanwhile, Andie's dorky best friend, Duckie, is secretly in love with her. Released in 1986, "Pretty in Pink" is a cult classic that everyone should check out.

Teen rom-coms might have briefly fallen out of style, but they're back and better than ever — as proven by "To All the Boys I've Loved Before." The movie based on the book of the same name immediately became a must-see hit when it dropped on Netflix in 2018 thanks to its witty dialogue, refreshing casting and charming plot. Lana Condor stars as Lara Jean Covey, a high school junior who's written love letters to all her crushes instead of telling them how she felt. When the letters are stolen and mailed out, Lara starts to pretend-date popular classmate Peter Kavinsky, played by Noah Centineo, as a distraction. Of course, their fake romance soon becomes the real thing. Aww!

"Easy A" has to be one of the most creative teen films we've ever seen. Loosely inspired by "The Scarlet Letter," "Easy A" follows Olive, a clean-cut student who decides to spice things up and lie about losing her virginity. Her little white lie soon turns her life upside down, but Olive finds happiness (and love) with the school mascot, Todd. "Easy A" is the film that helped propel Emma Stone to super-stardom and solidified Penn Badgley as a total heartthrob. Entertaining, hilarious and original, "Easy A" is definitely top 20.

No high school rom-com list would be complete without this classic! 1963's "Bye Bye Birdie" is one of the first teen romance movies to come out of Hollywood. The legendary musical stars Ann-Margret as Kim MacAfee, a lucky high school girl who's selected to kiss young rock 'n' roll star Conrad Birdie before he heads off to war. The kiss causes problems for her high school sweetheart Hugo Peabody, played by Bobby Rydell, but the couple reunites in the end. "Bye Bye Birdie" delighted audiences back in the '60s and continues to do so today. Love!

Amanda Bynes lived out every American girl's British crush fantasy when she starred in 2003's "What a Girl Wants." In the teen rom-com, Daphne travels to England to find her father, who just happens to be Lord Henry Dashwood, a politician and member of the British upper class. While there, Daphne mets musician Ian Wallace and sparks fly. Amanda, Colin Firth and Oliver James all star in this super-cute flick.