The Top Five Classic Rom-Com Films of All-Time

Valentine’s Day: the one day each year when it’s somewhat okay to publicly declare your love to someone or even create a giant cut-out of your significant other. It’s also the best day of the year to watch rom-coms (romantic comedies), one of the best genres of film ever made. But there are simply too many to watch without drowning in cheesy confessions and awkward make-out sessions, so I’m here to make your life a whole lot easier. Sit back, grab some popcorn, and get ready to discover the top five rom-com movies of all time.

Since I’m too weak-hearted to actually rank the top five, I’ll be listing them in no particular order. First up we have The Proposal starring Sandra Bullock and Ryan Reynolds. Bullock stars as a Canadian executive who finds out she may face deportation from the U.S. because the renewal of her visa was denied. To keep her position at her company and remain in the U.S., she convinces her miserable personal assistant (Reynolds) to act as her fiance, but it’s only an act for so long. The Proposal, while cheesy and cliche, is hilarious, cute, and worth the watch. 

Next up is 13 Going on 30, starring Jennifer Garner and Mark Ruffalo. Garner plays Jenna Rink, a 13-year-old girl originally from 1987, who wakes up to find herself to be 30 years old in 2004 after she wishes to be “30 and flirty and thriving.” 13 Going on 30 is a movie filled with humor, nostalgia, self-empowerment, and a whole lot of love.

Third on the list is 50 First Dates, starring Drew Barrymore and Adam Sandler. The film follows Lucy Whitmore (Barrymore) an art teacher who has amnesia and forgets each day after she falls asleep and Henry Roth (Sandler), the womanizing marine veterinarian who falls in love with her. After discovering Lucy loses her memories each night, Henry decides to win her over again each new day. 50 First Dates is hilariously charming, showing that when you truly love someone, there are no bounds to how far you’ll go for them. This is Barrymore and Sandler’s second film together after The Wedding Singer, another rom-com worth checking out! 

Up next is How to Lose a Guy in 10 Days, arguably one of the best movies of all time. Kate Hudson and Matthew McConaughey star as a women’s magazine writer and an advertising executive respectively, who both begin a relationship with each other with ulterior motives. Though it’s predictable, Hudson and McConaughey share immaculate chemistry and manage to make even the grumpiest of people smile. Definitely a must-watch!

Now, I know I said I was too weak-hearted to actually rank the top five, but I do have a favorite on the list. The absolute, undeniable best rom-com movie of all time is 10 Things I Hate About You, starring Julia Stiles and Heath Ledger. The film follows Cameron James (Joseph Gordon-Levitt), a new student after he falls in love with Bianca Stratford (Larisa Oleynik). However, there’s a catch: Bianca can’t date until her older sister, Kat (Stiles), does, and oh boy is Kat a character. Cameron hatches a plot to get Patrick Verona (Ledger), the “bad boy,” to date Kat, who let’s just say discovers ten things she hates about him. It isn’t even an argument about how good this movie is: it’s a 100/10! It is the definition of a classic teen rom-com with every ounce of cringey romance and cheesy jokes. A cult classic! Fun fact: the movie is actually a modern adaptation of Shakespeare’s Taming of the Shrew. Watching 10 Things I Hate About You is not a recommendation, it is a must!

Before I close this out, I also have some honorable mentions: Hitch, Love & Basketball, Sleepless in Seattle, and She’s the Man. All amazing choices for when you’re in the mood for some love and laughs. Enjoy your Valentine’s Day!