I was 8 years old when I first saw Rob Reiner’s “The Princess Bride,” a romantic comedy wrapped in the trappings of a fantasy, to delight young girls and fool young boys for decades to come. It paved the way for a life where part of my brain is always thinking about Shopgirl and NY152 from “You’ve Got Mail,” or how Cher goes to the opera with Nicolas Cage in “Moonstruck,” or when Bill Pullman describes leaning to Sandra Bullock in “While You Were Sleeping.” But what makes a good rom-com? And why are so few of them great?
In the wake of the recent heartbreaking losses of rom-com icons actress Diane Keaton (“Annie Hall” and “Something’s Gotta Give”) and Reiner himself (“When Harry Met Sally,” and “The American President”), those questions have been top of mind — and are nearly impossible to answer with any level of satisfaction. So, instead, I offer a paean to the genre, a guide to those interested in opening their moviegoing hearts a bit wider. Because you never know what, or who, might be waiting in the shop (or movie theater or streaming service) around the corner.
IF YOU LIKE: Zippy, screwball workplace romances
“His Girl Friday” (1940), from director Howard Hawks, showcases Cary Grant and Rosalind Russell as ex-spouses (a newspaper editor and investigative reporter, respectively) looking unbelievably glam and engaging in the most perfect banter. It pairs perfectly with Claire Scanlon’s “Set It Up” (2018), starring Zoey Deutch (born for this) and Glen Powell (in his best role to date) as workplace frenemies looking to matchmake their bosses (the electric Lucy Liu and Taye Diggs) to reclaim their own social lives.
IF YOU LIKE: Modern adaptations of literary classics that don’t feel like homework
Amy Heckerling’s “Clueless” (1995) stages Jane Austen’s “Emma” in the mid-’90s Valley, as if there could be any better place for teen matchmaking and social hierarchies. Taking notes was “Fire Island” (2022), directed by Andrew Ahn and written by and starring Joel Kim Booster. A group of queer friends gathers for their annual trek to the titular location, where Austen’s “Pride and Prejudice” takes flight. There are misunderstandings and mansions and Conrad Ricamora as a new cinematic Mr. Darcy. <<hand flex>>
IF YOU LIKE: The age-old debate of whether men and women can ever just be friends
As time passes, and my own views on love and friendship and happiness shift and redefine, “When Harry Met Sally” (1989) — written by rom-com north star Nora Ephron, directed by Reiner, and starring Billy Crystal and Meg Ryan — only becomes more poignant and relevant and hilarious. Every choice holds up and every viewing reveals a new, beloved detail. I could talk about this movie for, conservatively, 100 hours. The underseen will-they-or-won’t-they-but-they-probably-will “What If” (2013) brings a similar energy, and was early proof that Daniel Radcliffe is no fluke. And, in true WHMS spirit, it boasts a pair of well-cast supporting characters in Adam Driver and Mackenzie Davis. (The film also leans into its roots by staging a meet-cute (IYKYK) at a screening of “The Princess Bride.”)
IF YOU LIKE: A rom-com that works to expand the genre
“My Best Friend’s Wedding” (1997), helmed by P.J. Hogan, puts bona fide movie star and America’s sweetheart Julia Roberts in the seemingly miscast role of spoiler to the romance of Dermot Mulroney and Cameron Diaz. Turns out it’s a great look on her, and that iconic smile goes a long way toward directing the audience’s sympathies and allegiances. As far as stars go, Queen Latifah has been a name since the late ‘80s, and in Wayne Wang’s “Last Holiday” (2006), she is incandescent as a woman having what she believes is her final hurrah following a terminal diagnosis. She puts a charming spin on what is primarily a male-led story trope. And, if you’re looking for something in the barely worn timeloop territory (a la “Groundhog Day”), seek out Max Barbakow’s “Palm Springs” (2020). Andy Samberg and a standout Cristin Milioti are on a quest together to figure out how to break the endless cycle of one of Milioti’s worst days. There’s a free-for-all quality to this film that works so well in concert with the evolution of their relationship.
Johanna Lester is a pop culture critic who mainlines movies, TV and the best cookies Rochester has to offer. She’ll also hold that grudge on your behalf. Follow her @theauntjojo.
