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Sunday, Dec. 21, 2025

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Five Pre-2000s Rom-Coms to Watch This Valentine’s Day

Reading time: about 6 minutes

In 2023, AnyoneBut You raked in an impressive $220 million worldwide on a budget of only $25 million, which many interpreted as a sign of a potential romantic comedy revival in the modern film industry. However, some critics argued that the film ultimately failed to include one of the most crucial aspects of romantic comedies: on-screen chemistry. I’d place myself alongside those critics. The film casts Glen Powell and Sydney Sweeney — two extremely conventionally attractive actors — in the roles of everyday singles, which hinders the film’s ability to allow audiences to connect completely with the characters and story. Additionally, the plot relies heavily on many absurd comedic situations and romantic tropes, rather than moments that highlight a true bond between the two characters. This results in a viewing experience that is neither enjoyable nor realistic. 

Like many other rom-coms released since the 2000s, Anyone But You embodies a very artificial and cold approach to filmmaking. For this Valentine’s Day, instead of viewing a sad, tired attempt at capturing one of the most powerful feelings known to man, watch one (or more) of the classic, charming rom-coms on this list.

For those interested in expanding their horizons to classic Hollywood cinema, Billy Wilder’s The Apartment (1960) is a must-watch. The film follows Jack Lemmon as C.C. Baxter, an insurance worker who lends his apartment to his superiors for their extramarital affairs in exchange for high ratings on performance reviews. Baxter develops feelings for an elevator operator at his office building, who has a secret relationship with one of Baxter's married superiors. The story carefully balances powerful themes of infidelity, depression and the crushing nature of office politics with moments of genius comedic acting delivered by Lemmon. The Apartment stands as one of the most unique rom-coms I’ve watched, with brilliant cinematography and writing only further enhancing its wonder.

The Princess Bride (1987) possesses some characteristics atypical for the average rom-com, but delivers on the themes of love in one of the most endearing and memorable ways possible. Structured as a fairy tale being read by a grandfather to his sick grandson, the story follows a swashbuckling hero (Cary Elwes) as he seeks to rescue Buttercup, played by Robin Wright, from an arranged marriage to the region’s selfish prince. The ensemble cast features a number of acclaimed actors such as Mandy Patinkin, Chris Sarandon, Wallace Shawn, André the Giant, Peter Falk and Billy Crystal. The Princess Bride presents a hilarious, modern take on traditional fairy tale tropes, with memorable scenes coming one after another. 

It goes without saying that When Harry Met Sally (1989) deserves a spot on this list. Perhaps one of the greatest examples of the friends-to-lovers trope, When Harry Met Sally stars Billy Crystal and Meg Ryan in the titular roles as friends who experience difficult romantic relationships before eventually developing feelings for each other. Though a seemingly simple concept, the beautiful cinematography, witty banter and nostalgic soundtrack (complete with artists like Harry Connick Jr, Frank Sinatra, Ella Fitzgerald and Louis Armstrong) create one of the most heartwarming viewing experiences possible.

Though Feb. 2 has already passed, it’s not too late to watch Groundhog Day (1993). Bill Murray stars as Phil Connors, an arrogant weatherman tired of his annual trips to Punxsutawney, Pennsylvania for Groundhog Day. A pioneer of the “time loop” genre, Groundhog Day depicts Connors as he is forced to repeat his least favorite day over and over again. During the loop, however, Connors discovers his romantic feelings for his producer Rita Hanson (played by Andie MacDowell). Groundhog Day boasts some of the funniest scenes out of any rom-com, with Murray and the supporting cast delivering on the script brilliantly. The film also delves into themes of redemption and grief, with the entire time loop cycle acting as a sort of purgatory that punishes Connors’ worst qualities. The story also defies many common rom-com tropes, with Connors’ attempts to woo Hanson by collecting information on her life failing miserably.

Finally, 10 Things I Hate About You (1999) allowed itself to enter this list at the buzzer, being released just months before the start of the 21st century. Based on William Shakespeare’s The Taming of the Shrew, the film follows two sisters, Kat and Bianca Stratford (played by Julia Stiles and Larisa Oleynik respectively) whose father will only let Bianca, the younger sister, date if Kat does so first. A new student named Cameron James (played by Joseph Gordon-Levitt) enlists rebellious student Patrick Verona (played by Heath Ledger) to date the intimidating Kat so that he will be able to date Bianca. The cast of 10 Things I Hate About You delivers lines masterfully between each other, and the Shakespearean tale is adapted to the modern age with impressive success. The drama between the characters never seems forced, with the actors creating natural and coherent personalities for the vast majority of the film.

If new rom-coms truly wish to cement themselves in the cultural landscape like these films, they must pursue innovation and subversion rather than attempt to recreate previous storylines or shove empty relationships between attractive actors down our throats. I hope that the next decade will see a return to the charm and wit of the films on this list or the comedic genius of films like Forgetting Sarah Marshall and Knocked Up. Otherwise, I fear that rom-coms will be one of the more soulless aspects of the film industry, alongside unwanted sequels and remakes. 

Matthew Rentezelas is a freshman in the College of Arts and Sciences. He can be reached at mmr255@cornell.edu.


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