#POPCULTURE | You Aught-a Know: The Wonderful World of 2000s Rom-Coms
by Thandie Aliño
The romantic comedy, or rom-com, is unfairly treated, often unceremoniously recognized as “fluffy,” “trashy,” “schmaltzy,” and “corny.” A chunk of that derision has to do with its conflation with the “chick flick,” or movies primarily marketed to women. The lack of respect for media targeted towards the female demographic is hardly a new phenomenon, but most forget that the rom-com is not some new fad. In fact, the genre dates all the way back to Shakespeare, where his plays Much Ado About Nothing, A Midsummer Night’s Dream, As You Like It, and Twelfth Night all precede the zany hijinks, razor-sharp wit, and tangled plots we see in rom-coms today.
It’s admittedly not hard to see why some recoil since the most visible examples of the genre are rife with twee clichés: the meet-cute; opposites attract; a kiss in the rain; and the third-act misunderstanding, break-up, and subsequent reunion. There are valid criticisms of the genre, including the lack of representation of persons of color and LGBTQIA+ people as romantic leads, but the one characteristic everyone seems to pile on is its heightened quality. Such criticism fails to recognize that the rom-com, at its heart, is an escapist fantasy. Sense is made out of senselessness, persistence is rewarded, and love is found in the most hopeless of places.
Our personal hardships may seem insurmountable, but letting a film designed to make you feel good take the reins for 90 minutes is a brief respite before tapping back into the ring we call real life. All you need to do as a viewer is to suspend your disbelief and hop into a fantasy crafted in good faith.
In this list of picks solely sourced from the 2000s, a decade wrongly prescribed as the period where the quality and credibility of the genre declined, you will hopefully find a film in one of these four tiers that appeals to you.
TIER 1: The Typical Rom-Com
These are the ones that pop into most minds when the word “rom-com” is mentioned.
Initial friction between two people is a well-worn trope that you can find in almost any rom-com. Mild annoyance between washed-up boy band singer Alex and Sophie, the woman he’s writing a song with, blossoms into infatuation in Music and Lyrics, and the cultural differences between cynical modern woman Kate and optimistic 19th-century nobleman-out-of-time Leopold shift into tender understanding in Kate & Leopold. Playful deceit is also a common trope, with a classic example being How to Lose a Guy in 10 Days, where hijinks ensue when advice columnist Andie and business executive Ben’s respective bets on each other backfire.
Looking for a hilarious, star-studded intersection of multiple storylines? In Crazy, Stupid Love, when Cal, a man caught amidst a mid-life crisis brought on by his impending divorce, employs the help of playboy Jacob in snagging dates, he sets off a course of events that lead to the famous, hilarious climax. How about a heartwarming condensed version of the How I Met Your Mother premise where Will, another soon-to-be divorcee, tells a story to his youngest daughter about three very different women, one of whom may be her mother? Definitely, Maybe may be for you.
For a detour down to Great Britain, Bridget Jones’s Diary is a great gateway, with the flawed yet charming eponymous protagonist caught between two men vying for her affection. Imagine Me & You is also similarly delightful, as its story of wide-eyed bride Rachel was drawn to charming florist Luce at her wedding functions as both a romance and a journey of self-discovery.
However, if you’d like a light double feature directed by one of the most successful female filmmakers of all time, Something’s Gotta Give and The Holiday are the way to go. Nancy Meyers makes a living out of creating movies that radiate pure comfort, but she’s best at centering the careers and personal lives of middle-aged women who find romance at the most unexpected time in their lives. In Something’s Gotta Give, it’s successful playwright Erica thrown into an awkward situation, as she is left to care for record company exec Harry, her daughter’s much older beau, following his taxing heart attack. In The Holiday, it’s the parallel plotlines of British woman Iris and the US-based Amanda, who swap homes for the holidays and end up finding love with a man in each other’s homelands.
TIER 2: Hidden Gems of the Typical Rom-Com
Despite the appealing selection of films above, they still center affluent, white protagonists. Most rom-com recommendation lists tend to stop there. Not this one!
You’ve heard of Pride and Prejudice, but how about Bride and Prejudice? This rousing hybrid of Bollywood art direction and Hollywood tropes is an alternative take on the classic Jane Austen story, wherein Elizabeth Bennet is replaced by fiery young Indian woman Lalita Bakshi, and the themes of classism extend into anti-imperialism and interculturalism. Excellently choreographed dances and catchy tunes spring from its Bollywood roots, with a musical highlight being the peppy “No Life Without Wife.”
From there, you can segue into the entertaining Hitch, where the titular dating coach finds his own call to romance. There’s also the criminally underseen Brown Sugar, an adoring love letter to hip-hop, which acts as the medium that brought Sid and Dre together as children and as a metaphor for passion and authenticity. Love & Basketball is the more realistic side of the coin of childhood-friends-to-lovers, with Monica and Q loving each other while striving towards their individual dreams of playing big-league professional basketball. All center Black protagonists, focusing on important themes from gender disparity to career practicality, while retaining sentimentality.
Saving Face similarly subverts the idea that rom-coms can’t hold weight. Its love story between two women, the shy doctor protagonist and an outgoing dancer, emerges in the frame of the sociocultural expectations within a small New York-based Chinese community and the doctor’s complicated relationship with her conservative mother. Despite all that, the film exudes warmth and gentility, giving grace to a culture instead of demonizing it.
Down the path, we finally reach the Philippines, our home plate and the setting for the following triple delight. In Got 2 Believe, mischievous wedding photographer Lawrence and flighty wedding planner Toni link up despite their very different views on love. In A Very Special Love, the cheery Laida will find a challenge in both love and career with Miggy, her demanding new boss and celebrity crush. Lastly, Till There Was You offers up a strange premise of free spirit Joanna hired by serious lawyer Albert to act as his daughter Pippa’s mother, as the young child is under the impression that Joanna is the mother she’s been waiting for all her life. All set the stage for numerous modern love team vehicles, while they themselves achieve iconic, unreplicable singularity.
TIER 3: The Weird and the Wild
For some, typical just won’t cut it. Even then, there’s a rom-com for them.
Described by director Paul Thomas Anderson as an “arthouse Adam Sandler film,” the absurdist Punch-Drunk Love is about the socially inept Barry and the gang of scammers threatening to upend the high he’s on following a blossoming romance. If you’re game to step into the intensely immersive reality of eternal anxiety (coupled with some tenderness), this one’s for you.
And if you yearn for something stranger, there’s I’m a Cyborg, But That’s OK to quench your thirst. Set in a mental institution, this oddity of a movie follows the deceptively simple mission of serial stealer Il-soon: to get his fellow patient Young-goon to eat, with her firm belief that she is a cyborg who should not consume food being the only thing stopping him from succeeding. It is as hyper-stylized, bizarre, and touching as it sounds.
A self-aware deconstruction of boy meets girl and the perfect, idealistic romance? That’s (500) Days of Summer for you. A campy action comedy about a goody-two-shoes spy-in-training falling for the supervillainess her agency is trying to catch? Run, don’t walk, to see D.E.B.S. The highly entertaining Watching the Detectives satirizes the manic pixie dream girl and sees video store owner Neil caught in a strange love affair with giddy troublemaker Violet, who plays mind games that amuse her and distress him. It’s great to watch with the whimsical Amélie, whose titular heroine is quite the charming disruptor herself, nudging the people around her to better lives and sending her beau on a wild goose chase around Paris for clues to find her.
A good end would be an Ewan McGregor double feature of some of his most overlooked films: Down With Love, a gorgeous pastiche of 1960s sex comedies wherein he plays a playboy journalist looking to find cracks in the veneer of a feminist advice author; and based-on-a-true-story yarn I Love You Phillip Morris, wherein he plays Morris himself, who is the object of affection of fellow inmate and con man Steve Russell and the reason for his lover’s many prison break attempts.
TIER 4: Love Does Not Define Me
By now, maybe you’ve caught a slight case of romantic fatigue and want to primarily focus on the female protagonist’s journey.
If you want magical realism in the form of a thirteen-year-old girl’s wish to wake up in her thirty-year-old self coming true, the fun and fluffy and thriving 13 Going on 30 is an amazing start. If you like weird, witty little indies about all the awkward, hilarious, and lovely things an unplanned pregnancy brings, then Juno is the one for you. An underappreciated pick would be Last Holiday, which is much more joyously life-affirming than its premise — a shy aspiring chef taking out all her savings and living it up in a European hotel following a terminal illness diagnosis — would have you believe.
How about rom-coms where love lies, too, in family and friends? My Big Fat Greek Wedding follows Toula, her journey of self-actualization, her relationship with the sweet, supportive Ian, and her struggle to get her family to accept him. It retains its lightness while exploring the nature of heritage, cultural identity, and community. Greece and weddings seem to be the theme to this double feature, as the iconic Mamma Mia! is an exuberant musical set on a Greek island where the vibrant Sophie invites her mother Donna’s three ex-lovers to her wedding in the hopes of finding her biological father, all to the tune of ABBA’s greatest hits.
The final star of this list is Anne Hathaway, whose Ella Enchanted (bright young woman who’s compelled to always do what she’s told goes on a journey to find the fairy godmother who can reverse this curse) and The Princess Diaries duology (bright young woman finds the self-confidence to lead the kingdom of Genovia) are both enjoyable, kid-friendly royal adventures that act as the perfect childhood gateways into the rom-com.
Now that we’re at our end, you’ve probably found potential comfort favorites for unwinding after the next period of exams. If not, don’t stop at this list; go find more for yourself!
After all, as the rom-com wholeheartedly believes, everyone deserves a happy ending.
