Leslye Headland is the writer/director of the 2012 comedy Bachelorette and the writer of the 2014 romantic comedy hit About Last Night. Her latest film, Sleeping with Other People, starring Jason Sudeikis and Alison Brie, premiered at the 2015 Sundance Film Festival.
Headland describes the film as, “When Harry Met Sally, but for assholes.” CraveOnline called it “the best romantic comedy in many years.”
Ms. Headland has graciously accepted our offer to write a guest editorial for Valentine’s Day, highlighting romantic comedies – or “Rom-Coms” – that everyone can enjoy, even if they hate Rom-Coms.
Probably the most hated film genre today is also one of the oldest. The romantic comedy was born around the time sound was introduced in cinema. It has remained a multiplex staple to this day. While prepping my second feature, Sleeping with Other People, I took a look at how the romantic comedy has morphed and evolved in order to write and direct one for the twenty-first century.
For Valentine’s Day, I’ve compiled a list of some benchmark examples and perversions of the Rom-Com that you can enjoy, guilt-free, with or without a date this weekend!
Related: Leslye Headland & Jason Sudeikis Talk ‘Sleeping with Other People’ (Exclusive Video)
The Shop Around the Corner (1940)
You’d have to be without a pulse to dislike this beautiful gem by mastermind of the early romantic comedy, Ernst Lubitsch. It has all the set pieces we still use today but imbued with real pathos and style. It was remade as the semi-decent Meg Ryan-Tom Hanks vehicle, You’ve Got Mail, in 1999. But nothing beats the famed “Lubitsch Touch”.
The Lady Eve (1941)
Think romantic comedies are predictable? Check out this plot-twister from downright weirdo Preston Struges. Henry Fonda plays a clueless but loaded geek and all-around goddess Barbara Stanwyck plays the exact type of predatory sharp-witted lady who falls for that brand of idiot. It’s hard to tell what’s sexier: the stars’ brazen chemistry or Sturges’ wild visual style.
The Apartment (1960)
Every episode of Mad Men’s first season is just trying to be this complicated and beautiful Best Picture-winning film by Lubitsch protege, Billy Wilder. Juggling infidelity, suicide and workplace politics, Wilder and the perfect cast oscillate back and forth between heart-warming and heart-wrenching. Not to be missed.
Related: CraveOnline Picks The 50 Most Romantic Movies Ever Made
The Odd Couple (1968)
One of those films that’s so often imitated and so embedded in pop culture (from ubiquitous high school productions to the slightly above par TV sitcom version) that it’s hard to recommend the original film without inspiring groans. But it’s the laugh-out-loud tour de force perfs of Jack Lemmon and Walter Matthau that make any recent “bromantic” comedy pale in comparison.
What’s Up Doc? (1971)
This is the toughest sell on this list. Due to the fact that I’ve found it practically impossible to talk a man into a film with Barbra Streisand in it. But I swear to God, Peter Bogdonavich’s screwball comedy is worth the watch. A swing-for-the-fences Rom-Com during the Bad Boy filmmaker era of the 70s. Bonus: it boasts a debut screen performance from Madeleine Kahn.
Working Girl (1988)
This Mike Nichols-directed comedy/drama/romance has got everything. Sex. Romance. Money. Power. Harrison Ford. It ushered in the “Cinderella” era of Rom-Coms with a heroine as playful as the title. She was neither slut-shamed nor punished for her ambition. Her triumph was professional AND personal. Too bad no one followed suit for the next two decades.
Related: Sundance 2015 Review: ‘Sleeping with Other People’ is Totally Hot
French Kiss (1995)
Out of all the Meg Ryan Rom-Coms of this era, why pick this one? Maybe it’s Kevin Kline playing a dirty Frenchman? Maybe it’s that Ryan’s character is downright desperate and sad? Maybe because it’s helmed by one of the greatest screenwriters of all time, Lawrence Kasdan. I don’t know. Maybe the same reason I fall in love with the shitty men: Just ‘cause.
There’s Something About Mary (1999)
Here me out. Sure the Farrelly Brothers’ brand of slapstick doesn’t immediately make you think “Rom-Com”. But this entry in their canon not only has heart, it was a turning point for the genre. A male perspective, overtly sexual humor and an array of over-the-top supporting players meant that moving forward, the Rom-Com could and would be boy-friendly.
Punch-Drunk Love (2002)
After Magnolia, the LAST thing we thought visionary P.T. Anderson would make is an Adam Sandler movie. Even though it doesn’t adhere to any strict rules of the genre, it’s a compelling romance that inspired many dreamy imitators in the ’00s. Also, the opening is a perfect metaphor for love: A massive car accident that results in an instrument you have to teach yourself to play.
The Proposal (2009)
For the last decade and a half, the Rom-Com has been dominated by dynamite male director/lead combos like Apatow/Rogen or Stoller/Segel. But this box office hit boasts the only credible use of the “battle of the sexes” trope in recent history. Lurking beneath the broad set pieces is a sly exploration of today’s unbalanced sexual politics: the woman is the boss with her man as means to an end.
Appropriate Behavior (2014)
While Annie Hall will never have a cinematic successor, this micro-budget indie from writer/director/star Desiree Akhavan comes lovingly close. A love story told in flashback about a bisexual woman dealing with a break-upm, the film bucks the “mumblecore” trend and lands just left of a traditional Rom-Com. It achieves a difficult feat: it makes loneliness funny.
