With Valentine’s Day approaching, and romantic comedies [rom-coms] making an unexpected comeback, we have been tuning in on the classics throughout the years. With talented directors and infamous actors, many of these movies have made us laugh, cry, and want to watch more. Due to this, we have decided to rank our favorite 1990s and 2000s rom-coms through the careful consideration of characterization, plot development, and chemistry between the love interests.

While You Were Sleeping

“While You Were Sleeping” has some of the best chemistry from any rom-com. Sandra Bullock and Bill Pullman perfectly embodied the dynamics of a lonely person searching for love. While slow in some parts of the film, it deserves to be put on everyone’s ‘must watch’ rom-com list.

10 Things I Hate About You

“10 Things I Hate About You” has the perfect comedic nature to draw you in and make you fall in love with each of the characters. With Heath Ledger and Julia Stiles, his feel-good movie has earned a solid 4-heart rating.

Pretty Woman

“Pretty Woman” without a doubt is a 5-heart rating. The film perfectly exemplifies what it means to be a woman trying to find herself in the world. It also perfectly portrays how you don’t just need love to find joy, and how self-love rises above all else.

Known as ‘The Big Three,’ “When Harry Met Sally,” “Sleepless In Seattle,” and “You’ve Got Mail,” all have two things in common. All were produced by Academy Award nominee, Nora Ephron and all-star Golden Globe nominee Meg Ryan. All three films are perfect, partly because of Ephron’s astounding screenplay [script for the film] and her impeccable direction. She knows how to craft a script and conduct actors and actresses to get the perfect shot. Ephron has carved a stone in the foundation of romantic comedies, and without her, rom-coms would not be like they are today. Meg Ryan has mastered the art of rom-coms. She knows how to act and how to react to anything she is given. She is one of the best actresses of her time, and her impeccable acting shines through in these movies. These three rom-coms are superior above all else and should be considered as some of the greatest rom-coms of all time.

Gallery • 3 Photos

Photo Courtesy of Fair Use.

13 Going On 30

“13 Going on 30” has the perfect balance of comedy and romance. The juxtaposition between the mindsets of 13 and 30 years and the dynamic between the love interests made the movie unpredictable, giving it a 4-heart rating.

How To Lose A Guy In 10 Days

The romance between Kate Hudson and Matthew McConaughey is unmatched in “How To Lose A Guy In Ten Days.” They make the love and desperation between them feel so real and give the movie a flawless 5-heart rating.

The Proposal

Sandra Bullock and Ryan Reynolds are the true stars of “The Proposal.” The impeccable chemistry between the two isn’t found in many other rom-coms and makes the film shine as a whole.

Anyone But You

With the 2010s severely lacking new rom-coms that matched up to those made in the 90s and 2000s, Anyone But You, starring Sydney Sweeney and Glen Powell was a refreshing change from the new style of romantic comedies. The actors made you fall in love with their characters, with their personalities becoming the biggest stars of the film. The classic enemies-to-lovers trope made the movie feel nostalgic and new simultaneously, leaving the audiences in a feel-good mood when walking out of theaters, giving it a five-heart rating. See page 7 for more about the film.

Valentine’s Day

Most rom-coms follow the storyline of two characters and the perils they face in their relationship. “Valentine’s Day” is different and will always stand out from the rest. The film follows the plot of over 20 characters, most of which storylines are intertwined, and how they deal with the concept of love. All forms of love are shown in the film, from young love to old love, and breakups to marriages. With a cast stacked full of amazing actors such as Taylor Swift, Julia Roberts, Taylor Lautner, Anne Hathaway, Jennifer Garner, Ashton Kutcher, and so many more, “Valentine’s Day” will forever be a classic rom-com and will go down in history.