1995 | 1 hour 37 minutes | Directed by Amy Heckerling
 

Starry Alicia Silverstone, Stacey Dash, Brittany Murphy

There are many cases when a book-based movie turns sour, but Clueless is a stellar example of how such a movie should look and feel, I daresay. Loosely based on Jane Austen's 1815 novel Emma, Clueless is considered one of the greatest teen romantic comedies ever made. The film's success propelled young Alicia Silverstone's career and had us all swooning for Paul Rudd, adopting the "As if!" and wishing for the dazzling outfits from Cher's and Dionne's closets.

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!

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 touches always turn into comedy gold!

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.

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.

2006 | 1 hour 49 minutes | Directed by David Frankel
 

Starring Anne Hathaway, Meryl Streep, Adrian Grenier

The Devil Wears Prada is a comedy-drama based on Lauren Weisberger’s novel of the same name. Here, the plot centers around Andrea “Andy” Sachs - a young aspiring journalist who gets a job in the most prestigious fashion magazine. Here she has to work with a demanding boss, unempathetic co-workers and receives no help from her jealous, unsupportive boyfriend. However, Andy isn’t a weakling and she makes it all work in her own way. The Devil Wears Prada is one of those timeless chick flicks that is still generating new memes and quotes up to this day.

2000 | 1 hour 49 minutes | Directed by Donald Petrie
 

Starring Sandra Bullock, Michael Caine, Benjamin Bratt

Miss Congeniality is a 2000 comedy film directed by Donald Petrie, and starring Sandra Bullock. Bullock takes up the role of Gracie - a tomboy FBI agent sent to go undercover as a contestant at a Miss United States beauty pageant when a terrorist threatens to bomb it. Though it is a quite stereotypical fish-out-of-water story, Sandra’s charm totally evens it out.

2009 | 1 hour 48 minutes | Directed by Anne Fletcher
 

Starring Sandra Bullock, Ryan Reynolds, Mary Steenburgen

The Proposal, a 2009 romantic comedy, centers around the story of a Canadian executive (Sandra Bullock) facing deportation from the U.S. because of her expired visa. And what's the thing that makes the most sense in this scenario? Well, fake marriage, of course. So, she convinces her assistant (Ryan Reynolds) to play-act her fiance, and although he's quite reluctant at first, you know how it all ends. And if The Proposal cannot boast of its original plot, then the fresh and undeniable chemistry between Bullock and Reynolds makes it all up.

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.

2004 | 1 hour 38 minutes | Directed by Winick
 

Starring Jennifer Garner, Mark Ruffalo, Judy Greer

Though it's a bit unclear if this movie was meant to be for the thirteen-year-olds who at heart are at the age of thirty or vice versa, 13 Going On 30 is a thoroughly entertaining, magically nostalgic romantic comedy. The movie's protagonist Jenna, played by the charming Jennifer Garner, wakes up one morning at the age of thirty instead of thirteen and gets into a whole lot of funny misunderstandings figuring it out. Besides being quite a funny film, it also carries a strong and important message; though you'll have to watch the movie to know what it is!