In Honor of Valentine’s Day: My Top 5 Romantic Comedies

Columbia Pictures/Courtesy

Related Posts

Since it’s Valentine’s Day, I thought I’d start my weekly blog with giving you my personal list of the five greatest romantic comedies. If you still have no plans, I invite you to sit down with your special someone, share a bucket of popcorn, and pop any one of these love stories into your DVD player. They’re worth it.

“When Harry Met Sally…” (1989)

Rob Reiner’s direction, Nora Ephron’s script, Robert Leighton’s editing, Barry Sonnenfeld’s cinematography — these elements come together in a consummate way that demonstrates a unique love for movie love. The production team beautifully serves glorious performances from Meg Ryan and Billy Crystal, who create two indelible cinematic characters. “When Harry Met Sally…” is not a movie about cosmic forces bringing together soul mates; rather, it’s a movie that shows us that love is something made possible when you meet the right person with the right history at the right time.

My Best Friend’s Wedding” (1997)

Unlike “When Harry Met Sally…,” the conception of love in “My Best Friend’s Wedding” is somewhat more generic. Its plot and end goals don’t require a genius to predict. What makes this romantic-comedy such a wonderful movie is the colorful and endlessly complicated heroine at its center. It’s never clear why Jules is so shaken up by Kim, her best friend’s fiance. Is it jealousy? Rivalry? Love? The film never resolves this — and it shouldn’t. Our feelings for someone are much more complicated to be reduced. Jules, played flawlessly by Julia Roberts, is no diamond-in-the-rough, but that’s exactly why we root for her a little too much: We see a part of ourselves all too clearly in her.

“Jerry Maguire” (1996)

At two hours and twenty minutes, “Jerry Maguire” feels quite lengthy for a romantic comedy. In fact, the movie doesn’t really follow the typical rom-com formula. Jerry’s career predicament and midlife crisis often overshadow the unusual romance that blossoms between him and his loyal assistant, Dorothy. Yet, as the story moves forward, their romance begins to take shape, and the film often feels empty when the two aren’t sharing the screen. If by the end the film begins to lose the razor-sharp cynicism and wit that made its beginning and middle so easy to relish, it makes up for this with emotional depth and beautiful lines, such as Rene Zellweger’s iconic phrase, “You had me at ‘Hello.’” The two stars make those 139 minutes fly by.

“You’ve Got Mail” (1998)

There’s a reason why I have two movies in this list headlined by Meg Ryan. Often praised as a romantic comedy queen, but routinely under-appreciated as an actress, Ryan demonstrates in “You’ve Got Mail” more than in any other film how much craft she puts into her performances. In Ephron’s movie, she delivers probably her most mature, humanly-inflected work of her career, always proving how adept she is at conveying character details through her perfectly timed gestures, looks, and line-readings. She even brings out the best in Tom Hanks, who is subtle and restrained whenever he shares the screen with Ryan. Both of them make “You’ve Got Mail” a palpable, touching, and relatable love story that is in many ways a more genuine and tangible romance than “Sleepless in Seattle.”

“One Fine Day” (1996)

A big reason why I love “One Fine Day” has less to do with the actual quality or particular achievements of this film than with my personal memories of watching the movie multiple times. I have very fond childhood memories of sneaking into my parents’ bedroom, slipping under the covers where my father lay half awake, and digging into a bucket of popcorn as the two of us watched reruns of this movie. I’m sure that my copious memories of these father-son moments had as much to do with my love for the film as anything actually happening in the film. But we don’t see movies in a vacuum, do we? Our regard for a film stems as much from the actual merits of the film as it does from our specific state when we watch it. I don’t wish to undermine, however, the quality of this movie. It’s not very original, but its two leads, George Clooney and Michelle Pfeiffer, have amazing chemistry that brings this story to life. It’s a movie I deeply treasure, and one which I hope you’ll come across and give it a chance. It deserves it.

Braulio is the lead film critic. Contact Braulio at [email protected].