As Valentine’s Day approaches rapidly, it’s the perfect time to enjoy a classic romantic comedy. Whether you are in a steady relationship, stuck in a talking stage, or hopelessly looking for one, romantic comedy is the perfect movie genre that everyone can enjoy. While prices are at an all-time high, what better way to spend this Valentine’s Day than cuddled up at home with yourself or someone you love while watching one of my Top 5 romantic comedies?
Please note: this list is almost certainly biased and highly opinionated, don’t hate the player, hate the game. Now onto the list!
#5 The Holiday (2006)
Though The Holiday may seem like a Christmas movie due to the title, it is actually just an extremely heartwarming romantic comedy that happens to take place around Christmas. Struggling after their breakups, two women, one from America and the other from England, decide to exchange homes during the holidays to escape their heartbreak. In their new cities, the two women find happiness and love. One of my favorite things about this movie is the casting, it stars Kate Winslet who is incredible in everything she’s ever done. Opposite her is Jack Black, this might confuse you because Jack Black is not known for being a romantic, heartthrob, but he absolutely thrives in this role and delivers a wonderful performance. The other couple played by Cameron Diaz and Jude Law are also fantastic in this movie. Both couples have incredibly genuine chemistry that makes the movie engaging and fun. This movie has everything, great chemistry, good writing, Jack Black, and not one love story, but two!!!!
#4 Set it Up (2018)
If you think the romantic comedy genre is dead, you obviously haven’t watched Set It Up which was released only six years ago. This movie follows two overworked assistants, played by Glen Powell and Zoey Deutch, who plan to free up their schedules by setting their bosses up with each other and thus setting themselves up. Nothing will top Glen Powell and Zoey Duetch’s chemistry in this movie, and I had a hard time believing it wasn’t real. Zoey Deutch plays such a relatable, quirky leading lady, and that energy is matched by an equally quirky but troubled Glen Powell. It also has a great supporting cast including Pete Davidson, Taye Diggs, and Lucy Lui. This movie is hilarious and has a silly, unique storyline. It is the perfect light-hearted rom-com to watch on Valentine’s Day.
#3 How to Lose a Guy in 10 Days (2003)
How to Lose a Guy in 10 Days, is hands down one of the best and most unique rom-coms of all time. This movie follows Andie Anderson, a writer for a fluffy women’s magazine, longing to write more serious pieces. Unable to write about what she really wants to, politics and the environment, she decides to write an article about how to lose a guy in ten days. Benjamin Barry is an advertising executive who is looking to land a big ad for a diamond company. In order to secure the ad, he must prove he can make a woman fall in love with him in just 10 days. The two ultimately fall into each other’s laps. When Andie begins sabotaging the relationship to lose him, Benjamin must work that much harder to make her fall in love, until their love eventually turns true. Kate Hudson and Matthew McConaughey have impeccable comedic timing and great chemistry. Kathryn Hahn plays an incredibly pitiful, but hilarious supporting character that adds to the humor in the movie. This movie will make you laugh, maybe cry, and it will definitely frustrate you as Andie denies and sabotages her relationship. It’s cute, cheesy, and makes for an incredibly fun and enjoyable two hours alright, alright, alright.
#2 10 Things I Hate About You (1999)
10 Things I Hate About You is a modern-day retelling of William Shakespeare’s The Taming of the Shrew, though it’s much less of a bore, sorry Will. Kat and Bianca Stratford are heavily controlled by their worrisome and overbearing father, in fact, Bianca has been forbidden to date anyone until her abrasive and independent older sister does, an incredibly unlikely event. That is, until the school bad boy, Patrick Verona, is paid to take Kat out, which proves to be a very difficult task. This movie is the perfect teen rom-com, it shows the difficulties of high school life, while also telling a fun and unique love story. The chemistry between the two leads played by Julia Stiles and the late Heath Ledger is relatable and believable. The writing is humorous and at times emotional and writes a strong and independent female character, unlike any other romantic comedy. The movie is supported not only by its writing and acting performances but also by its alternative, grunge-y soundtrack, while also featuring a heartfelt performance of Frank Valli’s “Can’t Take My Eyes Off You” from Heath Ledger that will make you miss his talent. All and all this movie is absolutely perfect. Mostly, I hate the way I don’t hate it, not even close, not even a little bit, not even at all.
#1 When Harry Met Sally (1989)
When Harry Met Sally is a timeless rom-com, starring none other than the romantic comedy queen herself, Meg Ryan, and her on-screen romancer, Billy Crystal. The movie begins when Harry’s girlfriend sets him and Sally up to drive together, from Chicago to New York, to the college they were both attending. The story then follows their series of chance encounters in the city over a number of years that leads to their friendship, and eventual romance. It asks and ultimately answers the question “Can men and women truly ever be just friends.” This movie tells a story of friendship just as much as romance. While at the surface, it may seem like Sally and Harry have absolutely nothing in common, it’s their contrasting personalities that make this story so heartwarming and endearing. Sally is a quirky, optimist and Harry is a sarcastic, pessimist, and it’s these traits that make their chemistry feel so genuine. Not only are the acting performances incredible but the writing and cinematography are just as notable. Writer, Nora Ephron, managed to make a film that is equally humorous as it is heartwarming, with one-liners that are still quotable to this day. Director, Rob Reiner, made me want to move to New York City with his beautiful shots of the city in winter and fall. This movie is incredibly well-rounded and the perfect film to watch at any time of year, especially Valentine’s Day.