Everyone who knows me knows that I am an avid romantic comedy viewer. Just last semester, I analyzed the ’90s rom-com revolution for a visual culture class. So, based on my extensive viewing experience, I have created a list of the best rom-coms from the past five decades for every hopeless romantic during the season of love.
The 1980s: “When Harry Met Sally”
I couldn’t make a list of the best rom-coms from the past five decades without including “When Harry Met Sally.” This movie is a classic for a reason.
Twelve-year enemies become lovers in a slow burn between Sally Albright (Meg Ryan) and Harry Burns (Billy Crystal). This film has many iconic parts that even those who have never seen the movie likely know, such as the “I’ll have what she’s having” scene recently referenced in a Super Bowl commercial for Hellmann’s mayonnaise.
Throughout this film, Albright and Burns share witty chemistry and explore the relationship changes made throughout someone’s life. It is a film that every rom-com lover must see at least once.
The 1990s: “10 Things I Hate About You”
“10 Things I Hate About You” is based in a Seattle high school. Protagonist Kat Stratford (Julia Stiles) is sought out by rebel classmate Patrick Verona (Heath Ledger). The intro of this movie reminded me of “Mean Girls,” with the new kid getting the rundown of all the cliques in the school. Most alluring, Bianca Stratford, Kat Stratford’s sister, isn’t allowed to date unless her extremely uninterested sister does. This leads Bianca’s crush to pay Verona to go out with Kat, so he can get a date with Bianca.
The movie is laugh-worthy as Verona becomes more interested in Kat and puts on several public performances of his appreciation for her.
The 2000s: “Pride and Prejudice”
This is my list, so I’m a bit biased and didn’t even investigate other 2000’s rom-coms. “Pride and Prejudice” had to make an appearance. The story, based on Jane Austen’s 1813 novel, moves me to tears with every rewatch as I fall in love with the characters again.
Stubborn Elizabeth Bennet, played by Keira Knightly, is of age to marry but has no interest. She is drawn to the town’s newcomer, the cold Mr. Darcy (Matthew Macfayden), and they play the classic enemies-to-lovers trope.
What I love most about this rom-com is how Mr. Darcy’s character develops through actions, not dialogue. These small stories between the lines are what really draws appeal to his seemingly selfish character. Following his sweet words, you can’t help but giggle and kick your feet.
The 2010s: “Leap Year”
Romantic comedies from the 2010s often lack the charm of their predecessors, so I reviewed several before landing on this one as the best choice. “Leap Year” is a rom-com I discovered during my research, and I am surprised I haven’t seen more appreciation for this film.
Anna Brady (Amy Adams) follows her boyfriend, Jeremy Sloane (Adam Scott), to Dublin, wanting to propose to him as part of an Irish leap-year tradition. However, throughout the whole movie, the best thing Brady ever has to say about her soon-to-be betrothed is that he is a cardiologist.
Due to bad weather and a couple of impatient choices, Brady finds herself in a pub in middle-of-nowhere Ireland owned by Declan O’Callaghan (Matthew Goode). Brady and O’Callaghan could not be more different. Brady is uptight and materialistic, while O’Callaghan is a carefree prankster who only wants enough money to keep his pub running. Brady pays O’Callaghan to get her to Dublin, and they find themselves as opposites attracted.
This movie is full of romance tropes like enemies to lovers, only one room and one bed available and a fish out of water. It follows the perfect rom-com plot to keep you wanting more between the two protagonists.
The 2020s: “The Holidate”
I watched “The Holidate” in December, thinking it would be a cheesy Christmas movie to have on in the background.
The rom-com’s trope is fake dating. Sloane Benson (Emma Roberts) and Jackson (Luke Bracy) are a good pair. They both find themselves without a partner over the holidays, while their social circles worry about their relationship status. Together, they create a plan to pretend to be together for every holiday that year that they’re both single.
They both grow feelings for each other but are never sure if the other feels the same. This movie has several comedic breaks and even stars Kristin Chenoweth as serial dater Aunt Susan. This just had to be my choice for the best 2020’s rom-com movie out yet.
“10 Things I Hate About You.” Photo courtesy of Deadline.