1999 | 1 hour 37 minutes | Directed by Gil Junger
 

Starring Heath Ledger, Julia Stiles, Joseph Gordon-Levitt
 

A modernization of Shakespeare's late-16th-century comedy The Taming Of The Shrew, 10 Things I Hate About You blessed us with breakthrough roles for Heath Ledger and Joseph Gordon-Levitt. Together with Julia Stiles, it makes for a very naturally charming cast that elevates this movie to new heights—centered, of course, around a high school setting, this movie's full of teenage drama and love.

2018 | 1 hour 39 minutes | Directed by Susan Johnson
 

Starring Lana Condor, Noah Centineo, Janel Parrish
 

To All The Boys I've Loved Before is a teen romantic comedy film based on Jenny Han's 2014 novel of the same name. Our main girl here is Lara Jean Covey. She has a habit of writing a letter to each of the love interests that she has. The letters, of course, are meant for her eyes only, but they nevertheless find their way to the addressees. Now Lara's life is turned upside down, and there's a lot of dealing to be done! Although To All The Boys I've Loved Before plays heavily on the teen rom-com tropes, the relatable characters and loveable cast elevate it to new heights.

2001 | 1 hour 55 minutes | Directed by Garry Marshall
 

Starring Anne Hathaway, Julie Andrews, Hector Elizondo
 

How do you amp up a regular Ugly Duckling story? Why, by making said duckling an heiress to a European kingdom! And that's precisely what we get to see in The Princess Diaries - a regular, clumsy, and unkempt American teenager transforming into a beautiful princess, fit to rule a country. Besides having the most iconic makeover sequence (which Anne Hathaway later repeated in several other movies), The Princess Diaries also gave us love, enjoyable humor, and awesomely played characters.

2014 | 2 hours 6 minutes | Directed by Josh Boone
 

Starring Shailene Woodley, Ansel Elgort, Nat Wolff
 

The Fault In Our Stars is a coming-of-age romance film based on John Green's 2012 novel of the same name. The story centers around Hazel and Augustus—two teens with a shared passion for the unconventional, exceptional wit and a love that sweeps them away. Their romance is truly a miraculous one given that Hazel's constant companion is an oxygen tank, and Augustus keeps on joking about his prosthetic leg, and they meet each other at a cancer support group. The Fault In Our Stars is a witty movie that's both heartfelt without being too soapy—a good addition to anyone's list.

1995 | 1 hour 37 minutes | Directed by Amy Heckerling
 

Starring Alicia Silverstone, Paul Rudd, Stacey Dash 
 

Classical novels seem to be an excellent inspiration for iconic teen movies. This time it's Jane Austen's Emma that has gotten a chance to broaden its appeal to the teens of the '90s (and the decades to come). Starring such sweethearts as Alicia Silverstone, Stacey Dash, Paul Rudd, and the late Brittany Murphy, this movie instantly gained a cult-like following for its fashion, catchphrases, and relatability. A thoroughly entertaining film even almost thirty years after its release!

2002 | 1 hour 41 minutes | Directed by Adam Shankman
 

Starring Mandy Moore, Shane West, Peter Coyote
 

A Walk To Remember is a coming-of-age romantic drama film based on Nicholas Sparks' 1999 novel of the same name. Here, two North Carolina teens are thrown in together due to unexpected circumstances. Being from absolutely different families, they find it hard to get along at first, but lo and behold, Cupid's arrow is already in motion. However, once a deep secret is revealed, their relationship learns the real meaning of love and fate. While at times A Walk To Remember might verge on the side of soapy, it is still one heck of a heartbreaking and heartwarming story!

2004 | 1 hour 37 minutes | Directed by Mark Waters
 

Starring Lindsay Lohan, Jonathan Bennett, Rachel McAdams
 

A staple movie of the naughties, Mean Girls gave us the Plastics, the Burn Book, and trying to make fetch happen. Not to mention wearing pink on Wednesdays and making us understand that the limit does not exist. And though you've probably already watched it, here are some facts about Mean Girls. This legendary teen movie was based on a book called Queen Bees and Wannabes by Rosalind Wiseman. It depicts the lives of high school teenagers so well that it is basically like watching a reality show (just so much better). The funnies in this movie are also not accidental, as the dynamic duo—Tina Fey and Amy Poehler—are playing vital parts both on- and behind the screen. And what these two touch always turns into comedy gold!

2016 | 1 hour 46 minutes | Directed by Thea Sharrock
 

Starring Emilia "Always The Khaleesi" Clarke, Sam Claflin, Janet McTeer
 

Me Before You is a romantic drama film based on Jojo Moyes's 2012 novel of the same name. The whole story centers around two people, and the first that we meet is Lou Clark. She's a small-town girl who's perfectly happy in her small world, even if she knows that she might not love her boyfriend or that her job is truly a meaningless one. The second party is Will Traynor—a man who suffered an accident and is now paralyzed. Fate brings them together, and both of their worlds burst into never-before-seen or felt colors.

2004 | 1 hour 35 minutes | Directed by Mark Rosman
 

Starring Hilary Duff, Chad Michael Murray, Jennifer Coolidge

As the name dictates, A Cinderella Story is a modernized version of the ancient fable. This time, it follows Samantha—a teenager with big aspirations, stuck under the tyrannic rule of her stepmother. There's most definitely the Prince line, too—now, he's a pen pal, hoping to meet our protagonist at a high school Halloween dance. Just like in a fairy tale, Sam's dreams come true, the awful stepmother is put in her place, and love conquers all. A sweet movie for a cozy evening!

2006 | 1 hour 45 minutes | Directed by Andy Fickman
 

Starring Amanda Bynes, Laura Ramsey, Channing Tatum  

She's The Man, a movie inspired by Shakespeare's Twelfth Night (see a pattern here?), follows Viola Hastings as she enters a boarding school in her brother's place. Of course, she has to pretend to be a boy to study there and play on the school's soccer team, so a "Sebastian" is born. She's The Man perfectly depicts the baffling experience of teenage love and the drama that comes with it; even with a girl in a boy's disguise, it's still very relatable.

2001 | 1 hour 36 minutes | Directed by Robert Luketic
 

Starring Reese Whitherspoon, Luke Wilson, Selma Blair
 

There's probably no other romantic comedy as iconic as Legally Blonde, and all because of the charms of Reese Witherspoon as Elle Woods. Here's a movie that shows us all the blonde girl stereotypes and triumphantly crushes them, all the while keeping a sunshine-y and witty atmosphere. And if you've missed Elle, Legally Blonde 3 is scheduled for a release this year!

2015 | 1 hour 41 minutes | Directed by Are Sandel
 

Starring Mae Whitman, Bella Thorne, Robbie Amell 
 

The DUFF is a high school teen comedy film based on the 2010 novel of the same name by Kody Keplinger. Here, the DUFF means "Designated Ugly Fat Friend," and in this case, it's the unsuspecting-of-her-title Bianca. Despite being named as such, Bianca puts away the distractions and tries to reinvent herself to attract her crush's—Toby’s—attention. Full of charm and wit, The DUFF is a good addition to any teen movie buff's roster.

2004 | 2 hours 3 minutes | Directed by Nick Cassavetes
 

Starring Ryan Gosling, Rachel McAdams, Gena Rowlands
 

The Notebook is a romantic drama film based on the 1996 novel of the same name by Nicholas Sparks. And boy, if this isn't a tearjerking adaptation! To put it in just one sentence would be a crime, but here's the basis of the story—a poor young lad falls in love with a rich, passionate lass. Their love is as strong as can be, but their social differences keep on trying to pull them apart. Where's the tearjerker in that, you ask? Well, rent this movie and try watching it up until the end dry-eyed. It's impossible.

2010 | 1 hour 32 minutes | Directed by Will Gluck
 

Starring Emma Stone, Amanda Bynes, Penn Badgley
 

Easy A follows the demise of a very quirky-yet-charming and reputable (also way smarter than her years) Olive Penderghast, played by the very quirky-yet-charming Emma Stone. The movie involves a hugely inflated, not really real coitus scandal that unravels some of the darker secrets in Olive's high school. But, of course, it all ends up better than expected and not without the help of our protagonist's dance-and-song number. Witty, funny, and quite unique, Easy A is one of our all-time favorites.

2012 | 1 hour 43 minutes | Directed by Stephen Chbosky
 

Starring Logan Lerman, Emma Watson, Ezra Miller
 

The Perks Of Being A Wallflower is a coming-of-age story that follows a teenager Charlie through his freshman year of high school. Unfortunately, his triumphs are set back, unbeknownst to him, by post-traumatic stress disorder, and his mental health rapidly deteriorates. However, with the help of his friends, Sam and Patrick, he gets his life back on track and even learns to love. A truly heartfelt story elevated by excellent performances of a star-studded cast.

2012 | 1 hour 35 minutes | Directed by Jonathan Kasdan
 

Starring Dylan O'Brien, Britt Robertson, Victoria Justice

The First Time is a teen romantic comedy film that follows the story of a shy senior and a down-to-earth junior as they fall in love over the course of a weekend. Although their love blossomed quickly, the real hardships still await—one of them is changing cities for college, the other one is staying in high school. Will their love prevail over a long-distance relationship? Well, check out The First Time and see how the story goes!

1999 | 1 hour 35 minutes | Directed by Robert Iscove
 

Starring Freddie Prinze Jr., Rachael Leigh Cook, Matthew Lillard

She's All That is a teen romantic comedy that has its roots in the most classic works—George Bernard Shaw's play Pygmalion and George Cukor's 1964 film My Fair Lady. With that information, you can be pretty sure of how it all goes in She's All That, right? Yes, there's a handsome jock, and of course, there's the shy mousey girl. And yup, you are right—the jock bets that he can turn her into the prom queen! A story as old as the Ugly Duckling, but nonetheless entertaining! Also, the on-screen charms of the leading pair are so strong they are almost palpable, and that's a huge plus for any romantic movie.

1987 | 1 hour 40 minutes | Directed by Emile Ardolino
 

Starring Patrick Swayze, Jennifer Grey, Jerry Orbach
 

Dirty Dancing, a romantic dance film based on its writer Eleanor Bergstein’s childhood, waltzed straight into the movie hall of fame upon its release. A love story between an uptown girl on vacation at a Catskills resort and a lower-class dance instructor will raise the temperature of any room and will have you spraining an ankle in trying to copy the legendary dance moves. The chemistry between leading actors Jennifer Grey and Patrick Swayze is so strong you can almost touch it, and it definitely adds up to the charm of Dirty Dancing.

2004 | 1 hour 53 minutes | Directed by Gary Marshall
 

Starring Anne Hathaway, Callum Blue, Julie Andrews
 

The Princess Diaries 2: Royal Engagement is a romantic comedy and a sequel to 2001's The Princess Diaries. Unlike the first film, this one isn't based on Meg Cabot's books and is an original story. Now, our princess Mia is settled in her home country of Genovia—life seems pretty perfect! However, she soon finds out that she's being primed for an arranged marriage with an English suitor. Sadly, this second The Princess Diaries installment did not turn out to be as amazing as its predecessor, but it is still a nice choice for a light entertainment session!

2010 | 1 hour 47 minutes | Directed by Julie Anne Robinson
 

Starring Miley Cyrus, Liam Hemsworth, Greg Kinnear
 

The Last Song is a coming-of-age teen romantic drama film developed alongside Nicholas Spark's 2009 novel of the same name. See a pattern here? It's either Shakespeare or Nicholas Sparks that has the most adaptations in the genre of teen romance somehow. But let's go back to The Last Song here—a rebellious young teen, Ronnie, is sent to spend the summer with her estranged father. There, she meets a dashing young lad, and as she's falling in love, she simultaneously regains the connection with her father. A fun and easy watch supplemented by a gorgeous original soundtrack!