Romantic-comedies at their best can serve as a beacon of light in times of deplorable darkness, so follow along as I complete the countdown of my personal favorite romantic comedies released since the year 1990. Why 1990? Because this is my list and I arbitrarily set the parameters. Also, since my two favorite examples of the genre were released prior to 1990, I wanted to set those aside for future articles to give them the appropriate spotlight they deserve. For your convenience, I am including the titles from my first list.
Now, let’s get into it.
Director: Rob Reiner
Writer: Aaron Sorkin
What screams romance and comedy more loudly than the story of a president, an environmental lobbyist, and a Congressional bill calling for a 20% reduction in carbon emissions? The answer, for most people, is many, many things. But with The American President, Reiner, Sorkin, and a top-notch cast manage to pull off a cinematic juggling act by combining earnest romance, sharp, if slightly partisan, political drama, and genuine wit to form an undeniably entertaining package that still resonates 25 years after its initial release.
The story centers on the president of the United States, Andrew Shepard (Michael Douglas) – a recent widower who narrowly eked out an electoral victory and now enjoys a 63% approval rating heading into an election year – and newly hired environmental lobbyist Sydney Ellen Wade (Annette Benning). Their auspicious meeting at the White House begins with Sydney criticizing Shepard’s political track record on environmental issues and ends with Shepard, obviously bewitched by her passion and beauty, asking Sydney if she’d “like to get a donut.” This spark of attraction leads to dating, which leads to controversy, which leads to tanking poll numbers and fervent debate about what is and is not the business of the American public when it comes to a president’s personal affairs.
While all of that sounds a bit heady for a fun rom-com, it’s the chemistry of the ensemble cast (which include such notables as Michael J. Fox and Martin Sheen) and the unique, rhythmic magic of Sorkin’s dialogue that provides an air of effervescent charm and catapults this movie onto my list.
Director: Gil Junger
Writers: Karen McCullah, Kirsten Smith
My favorite phenomenon in all of filmdom is the one where two movies are released in the same year with strangely similar settings and stories. You know what I’m talking about, things like 1997’s twin volcanic eruptions in Volcano and Dante’s Peak¸1998’s asteroid-striking-the-Earth-movies Armageddon and Deep Impact, and the fantastical, magical stylings of 2006’s The Prestige and The Illusionist. The subgenre of teen-rom-coms had its own brush with this phenomenon in 1999 with the release of She’s All That and Ten Things I Hate About You. Both films are based on literary source material (Pygmalion and Taming of the Shrew, respectively), and both plots revolve around a bet or transaction, which leads to deception, which inevitably leads to romance because, well, movies. But what is it that elevates Ten Things I Hate About You above its contemporaries, and pretty much every other teen rom-com ever made?
Maybe it is the charisma of a fresh-faced Heath Ledger and Julia Stiles, whose performances transcend the typical tropes of a teenage love story. Maybe it’s the well-crafted script written by Karen McCullah and Kristen Smith (who went on to write Legally Blonde, one of a handful of movies I consider to be “perfect”), which expertly hits all of the beats of a movie dealing with the teen experience – first love, angst, the perils of popularity, the confines of conformity, prom, and the pressures of plunging into the precipice of adulthood that every graduate feels at some level – without pandering or over-simplifying. These are complex characters in a complex story, and that alone puts it in the upper-echelon of the genre. But when you add iconic moments like Heath Ledger serenading Julia Styles with Frankie Valli’s “Can’t Take My Eyes Off You,” and Larisa Oleynik’s character Bianca punching the antagonistic underwear model Joey Donner (played by Andrew Keegan) in the face on the middle of the prom dance floor, you get one of the best movies of a year many consider to be the best in movie history.
Director: Norman Jewison
Writers: Diane Drake
Long before they shared a subdued sexual tension as Tony Stark and Aunt May in Spiderman: Homecoming, Robert Downey Jr. and Marisa Tomei lit up the silver screen in this underrated rom-com from 1994. Faith (Tomei) is a school teacher who has since she was 11-years old, been waiting to meet the love of her life – a man named Damon Bradley whose name was foretold by both a Ouija Board and a cheap carnival fortune teller. (It’s one of the few movies that uses a Ouija board as a plot device where it does not ultimately lead to a demonic or other-worldly possession; unless you are strongly anti-RDJ, in which case, YOU are a demon).
About to settle for the world’s most average podiatrist, Faith gets a phone call from a man whose name is… wait for it: Damon Bradley. The only problem is that he is in Italy and she is in Pittsburgh. So Faith does what any sensible about-to-be-married middle-school teacher would do: she runs to the airport in her wedding dress and boards a plane straight to Italy, where she finally finds the man of her dreams, only to learn that he is not the man she expected.
The plot has a certain cornball quality, but the total package is nothing but cinematic charm. From the cast (including great support roles for Bonnie Hunt, Fisher Stevens and Billy Zane), to the idyllic Italian locales, this movie was one of my 1990s household staples, and can still offer a breezy escape from the diurnal drudgery of 2020.
Director: Garry Marshall
Writers: J.F. Lawton
A ‘Cinderella’ story where you swap household servitude for sterilized street prostitution? I am all in! This is the movie that catapulted Julia Roberts to superstardom, made Hector Elizondo a household name (sort of), and exposed the world to the harsh cruelties of shopping on Rodeo Drive while wearing the wrong outfit.
Despite some of its more troubling aspects when viewed with the benefit of 30 years of hindsight, the movie remains ineffably charming and infinitely watchable. As with many of the movies on this list, a lot of that hinges on the star power and chemistry of the cast, and you cannot do much better than Roberts and Gere at this point of their respective careers.
Director: Woody Allen
Writer: Woody Allen
Is it okay to put a Woody Allen movie on a list of favorite movies these days? Do not answer that.
In what may be the last great movie from the man who pretty much set the standard for the modern rom-com with 1977’s Annie Hall, Woody Allen captures a certain je ne sais quoi with this magical tale of time travel to a land of artistic and literary giants. The film’s romanticized vision of 1920s Paris serves as backdrop to the nascent romance of Gil Pender (played by a never better Owen Wilson), and Adriana (a light and lovely Marion Cotillard), who seems to attract and inspire some of the greatest artists of her day.
If you love Paris, Ernest Hemingway, Cole Porter, Salvador Dali, Sydney Bechet, pseudo-intellectual banter, or the idea of watching Rachel McAdams return to her Regina George roots by playing one of the least likable characters of her career, then I highly recommend checking this one out (even if you’re not a fan of Allen’s typical work).
Director: David O. Russell
Writers: David O. Russell
Much of the criticism levied against the romantic comedy as a genre is centered around the sameness of their plots and their character archetypes. Silver Linings Playbook proves that you can hit all of the major beats of the genre while elevating it with layered characters, stellar performances, and delicate direction from David O. Russell.
Bradley Cooper and Jennifer Lawrence offer career best performances as Pat and Tiffany, two people drawn together by their distinct peculiarities and their pain. Their exchanges are often explosive, but they never verge into parody or melodrama. Somehow the entire relationship seems rooted in reality, which lends a weight to the relationships and heightens the stakes for our characters as it becomes abundantly clear that they might be the only two people on Earth equipped to handle each other romantically.
The film also features one of Robert DeNiro’s best late-career performances as Cooper’s father. In one particularly memorable scene, he offers his son some sage advice that has always stuck with me. Immediately following a ridiculous and comical ballroom dancing sequence, Tiffany is devastated to see Pat talking with his ex-wife, and assumes that their flame is being rekindled. As Tiffany runs off, Pat’s father grabs his son and tells him “When life reaches out to you with a moment like this, it’s a sin if you don’t reach back.” The speech accomplishes what the best of the genre should by inspiring its audience to embrace love when the chance presents itself.
Director: Nora Ephron
Writers: Nora Ephron
Joey Tribbiani of Friends fame once described You’ve Got Mail thusly: “Tom Hanks. Meg Ryan. They get mail and stuff.” That’s a pretty succinct summary of the movie, and yet, it is so much more. Hanks and Ryan established their unparalleled screen chemistry in Joe vs. The Volcano and Sleepless in Seattle, the former of which typically gets all the love when ranking the best rom-coms of the 90s. But You’ve Got Mail is, in my humble opinion, the far greater achievement.
It is the cinematic equivalent of hearty stew served on a frigid, rainy afternoon. It warms the soul and sets one at ease, distracting from whatever storm might be raging outside in the real world. Hanks plays Joe Fox, a millionaire owner of a mega bookstore chain whose very existence is a literal and existential threat to the livelihood of Kathleen Kelly, the owner of a quaint, independent children’s bookshop.
Plenty of elements of the story feel antiquated today, from the big Barnes and Noble style book chain feeling like an unstoppable retail juggernaut, to the frequent sounds of the dial-up tone as Joe and Kathleen log onto their AOL accounts in anticipation of hearing those three magic words: “You’ve got mail.” But the pure joy that this movie evokes in those who watch it will never get old. From the performances, to the soundtrack, to the New York City that may only exist in dreams and celluloid, You’ve Got Mail will undoubtedly endure in the hearts and minds of rom-com lovers for years to come.
Director: Nicholas Stoller
Writers: Jason Segel
When Peter Bretter (Jason Segel) bares his flaccid, floppy penis to his longtime girlfriend Sarah Marshall (Kristen Bell), and then promptly gets broken up with, you know you are in for something special.
For as outrageous and raunchy as some of the scenes in Forgetting Sarah Marshall are, what really solidifies this movie’s place on my last, and many others’, is the relatability of Peter’s heartbreak, and the lengths to which he is willing to go to overcome it. In this case, of course, he travels to Hawaii only to encounter the source of his despair with her new beau, Aldous Snow (a scene stealing Russell Brand who might be the best side character in a romantic comedy ever).
Peter’s romance with hotel employee Rachel Jensen (Mila Kunis) is not an obvious one; compared to other examples, it seems to develop more organically and, in the end, you buy into the connection. And while the romance is great, this movie truly shines when it comes to delivering unbridled laughter. Even more impressive, is that the source of these laughs is spread among an impressive roster of side characters. From Jonah Hill’s unhealthy infatuation with Aldous Snow, to Paul Rudd’s bizarre surf instructions, to Jack McBrayer’s struggle to fulfill his husbandly duties on his honeymoon, there is no shortage of funny to find on this Hawaiian vacation.
This is the only entry on this list that I would consider a “desert island” movie. It is infinitely watchable, and is definitely the one I would recommend for those who have a distaste for typical rom-coms because it verges closest to pure comedy.
Director: Andrew Stanton
Writers: Andrew Stanton, Pete Docter, Jim Reardon
Not every romantic comedy needs to involve witty dialogue, famous movie stars, or even human beings. Some reading this might vehemently disagree that an animated Pixar film ostensibly intended for children can be categorized as a rom-com, but Wall-E is not only one of the most beautiful films in the Pixar canon, it is also its most romantic.
Much praise has been showered on the little trash-compacting robot tale for effectively serving as silent cinema for its first 30 minutes, and deservedly so. It is pure storytelling, and the story it chooses to tell is that of a lonely robot who longs for connection and companionship amid the wasted ruins of an abandoned Earth. Though the odds are stacked against him given the circumstances, Wall-E finds the love of his life in EVE, the sleek, shiny robot sent down to assess the Earth’s habitability.
The film takes us through the paces of a Hollywood romance. EVE starts out rather hostile toward Wall-E and completely dedicated to her work (like so many rom-com heroines). Wall-E’s persistence breaks through her tough exterior, and the two develop a rapport as Wall-E introduces her to his life. Then, inevitably, EVE’s programming shuts her down and Wall-E does what any robot in love would do: he clings onto the side of a space ship and hurtles into the deep dark of space to save her.
Wall-E is everything you want a rom-com to be: funny, heartwarming, romantic, and ultimately a celebration of the triumph of love over the tyranny of programming.
Director: Roger Michell
Writers: Richard Curtis
It is a tale as old as time: a famous movie actress goes into a nondescript travel bookshop to purchase a guide to visiting Turkey, and instead finds lifelong romance with the awkwardly charming bookshop owner. Notting Hill is a modern fairy-tale; a gender swapped ‘Cinderella’ story with Hugh Grant as the commoner and Julia Roberts as the Prince(ss).
More so than any other movie on this list, it encapsulates all of the traditional conventions of the genre and executes them to near perfection: the memorable meet-cute, the quirky supporting cast, the super-charged chemistry from two stars at the pinnacle of their powers.
If aliens came down to Earth and asked to see the quintessential example of what we humans call a romantic comedy, this is the one I would show them, which is why it has earned the number one spot on my list.