She’s Gotta Have It (1986)
Spike Lee centres his acclaimed directorial debut on Nola Darling (Tracy Camilla Johns), a young Brooklynite juggling three boyfriends. Soon, however, they all find out about each other and demand that she commit to just one of them. Loosely inspired by the ancient Greek comedy Lysistrata, She’s Gotta Have It takes a humorous approach to issues that remain contentious for women in the dating world.
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Legally Blonde (2001)
Love, law school and some spit-take-level laughs come together in this crowd-pleasing sleeper hit. Reese Witherspoon stars as an unlikely academic overachiever who outshines her classmates (“What, like it’s hard?”) in an attempt to win back a boyfriend who isn’t worth her time. Luckily, fate steps in and steers her elsewhere. This rom-com is a laugh-a-minute lesson in never judging a blonde by her hair colour.
Crazy, Stupid, Love. (2011)
An all-star ensemble cast—Steve Carell, Emma Stone, Ryan Gosling, Marisa Tomei, Julianne Moore and Kevin Bacon—unite for interweaving love stories involving breakups, hookups and punch-ups. Carell as a wannabe womanizer under the tutelage of Gosling’s pro pick-up artist is comedy gold. Crazy, Stupid, Love. is filled with many shocking (for the characters) and laugh-inducing (for us) discoveries.
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Coming to America (1988)
This classic will get a long-awaited sequel in March, making it the perfect time to revisit the original. In this rom-com-meets-buddy-movie, Eddie Murphy plays a prince from the fictional Zamunda on a mission in Manhattan to find himself a bride. Obviously, things go sideways—even with his trusty aide (played pitch-perfectly by Arsenio Hall) assisting him. Murphy and Hall take on multiple characters throughout Coming to America, ramping up the hilarity with each subsequent role. Keep an eye out for Sexual Chocolate, the grooviest band of 1988.
She’s All That (1999)
Brace yourselves for a wave of ‘90s nostalgia courtesy of MTV’s The Real World, hacky sack and Two Pence None the Richer—all of which play a part in this remake of My Fair Lady (which is itself an adaptation of George Bernard Shaw’s Pygmalion). In She’s All That, Freddie Prinze Jr. takes a bet to give a prom queen-worthy makeover to an independent-minded art student (Rachael Leigh Cook). Romance takes the roundabout route, but when it arrives, it’s that much sweeter.
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How to Lose A Guy In 10 Days (2003)
In this feel-good flick, Kate Hudson plays a “How-To” writer at a popular women’s magazine who, bored by her current career trajectory, decides to make her own fun by embodying all the stereotypical ways women sabotage relationships. Meanwhile, Matthew McConaughey’s character has made himself his own uncomfortable bed to lie in: by betting he can get her to fall hopelessly in love with him. A zany and ultimately romantic cat-and-mouse storyline unfolds, with the wonderful Kathryn Hahn stepping into a supporting role as Hudson’s BFF.
Funny Girl (1968)
Want a “based on a true story” rom-com? Look no further than Funny Girl, the Barbra Streisand-starring musical that won the actress an Academy Award for her very first on-screen role. Streisand plays Fanny Brice, the famed Ziegfeld Follies performer, with Omar Sharif in the role of her charming gambler husband. For fans of musicals, this one’s a classic, spawning hits like “Don’t Rain on My Parade” and “People.”
He’s Just Not That Into You (2009)
Based on the best-selling self-help book of the same name, He’s Just Not That Into You is another ensemble cast comedy with romance at its heart. Ben Affleck, Jennifer Aniston, Drew Barrymore, Jennifer Connelly, Bradley Cooper and Scarlett Johansson play just some of the characters trying to navigate dating, love, marriage and divorce in the modern world. Not all of them are successful at it, but they’ll all make you laugh!
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Dear Ex (2018)
Dear Ex features an unlikely love triangle: after Zhengyuan dies, his ex-wife and secret boyfriend battle it out for his life insurance money. To further complicate matters, the dead man’s teenage son can’t figure out whose side he will take in the conflict. A storyline that might otherwise sink into sadness is buoyed by a quirky script and note-perfect performances from the film’s charming cast.
Just Friends (2005)
Ryan Reynolds is Canada’s comedy gift to the world—a fact that’s already evident in one of his earliest starring roles. Reynolds plays a high school outcast who, after receiving a romantic rejection from his bestie (Amy Smart), decides to leave his small town behind and become a successful L.A. record exec. All goes to plan until a train wreck pop star (Anna Faris) forces an unplanned stopover in the aforementioned hometown and Reynolds’ character is reunited with the girl who once broke his heart. Fun fact: Just Friends was filmed in Moose Jaw and Regina!
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The Secret of My Success (1987)
Some guys will go to great lengths to impress a girl. Michael J. Fox’s character, however, goes the extra step: assuming a fake identity and job title to launch his stalled career and win the heart of a co-worker. Set in the hilariously clichéd world of Wall Street power brokers (think: hostile takeovers and company limos), Fox pulls off physical comedy like no one else, changing from his mailroom uniform to a business suit in elevators and awkwardly fending off advances from the boss’s wife. Bonus: the movie has a killer ‘80s soundtrack, featuring Pat Benatar, Bananarama and Katrina and the Waves.
The Incredible Jessica James (2017)
Jessica Williams, a Daily Show alum and podcast host of 2 Dope Queens, stars in this refreshingly non-formulaic rom-com about two single people trying (and sometimes failing) to get over their exes. Social media has made it hard to avoid keeping tabs on the people you used to date—a fact the film’s two central characters bond over. Irish actor Chris O’Dowd plays Williams’ is-he-or-isn’t-he love interest, enchanting both viewers and her character.
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Alex Strangelove (2018)
At once a coming-of-age and coming-out story, Alex Strangelove sees its title character go out in search of himself in a sea of high school pressures and expectations. Things go awry when he and his girlfriend make plans to have sex for the first time—all while his attraction to another boy grows. If tragedy plus time equals comedy, then it’s safe to say that anyone who’s escaped the clutches of high school will find more than a few reasons to laugh with (not at) Alex.
Kicking and Screaming (1995)
The directorial debut of Noah Baumbach (Marriage Story) zeroes in on a group of quirky almost-adults unable to confront the fact that they’re about to be dragged into the real world. The film stars indie film stalwarts Eric Stoltz, Parker Posey, Chris Eigeman and Josh Hamilton, as well as Elliott Gould. Baumbach’s trademark—dark interpersonal and relationship humour—is already on full display, and perfect for movie lovers who don’t go for the “happily ever after” brand of rom-com.
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Always Be My Maybe (2019)
If there’s one Keanu Reeves cameo appearance you watch this year, let it be his epic walk-on in Ali Wong and Randall Park’s fresh twist on the When Harry Met Sally story. Reeves plays Wong’s short-lived love interest, chewing the scenery as a caricature of his Hollywood self while the two characters who are actually destined to be together remain divided by his comically massive ego. In classic rom-com style, however, it all works out in the end.
Scandal in Sorrento (1955)
A love square rather than a triangle—leave it to the Italians to further complicate romance—plays out in the romantic seaside town of Sorrento, where it seems that people simply can’t help but fall in love. The stunning and comically gifted Sophia Loren stars as—get ready for it—a fishmonger seeking to inspire jealousy in her fisherman fiancé.
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Stranger Than Fiction (2006)
Will Ferrell and Maggie Gyllenhaal play semi-star-crossed lovers in this fantasy-comedy from director Marc Forster (Finding Neverland). Ferrell’s IRS agent character begins to hear a voice in his head narrating his entire life—and learns from the narrator that he will soon die. Still, he’s eventually talked into pursuing a relationship with a woman he’s auditing (Gyllenhaal) in the hopes of finding out if his life story is a comedy or a tragedy. Like The Truman Show, Stranger Than Fiction offers a truly unique take on the rom-com.
Trainwreck (2015)
With a cast that includes Tilda Swinton and LeBron James, Amy Schumer’s Trainwreck (which she also wrote) was a surprise summer hit and also picked up two Golden Globe nominations. Schumer plays a love-averse magazine writer doing a piece on a Billy Joel-loving sports doctor (Bill Hader). Over the course of their relationship, she does everything she can to push him away, eventually succeeding. This being a rom-com, however, the story’s not over until Billy sings.
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Sex and the City: The Movie (2008)
Say what you will about Sex and the City’s slow decline towards being, well, unfunny, the film gets the Gang of Four back together, reuniting them for a refreshingly imperfect and funny finale. (Yes, we are pretending that the embarrassing sequel doesn’t exist.) Here, happy endings, like Manolo Blahniks, come in various shapes and sizes. You just have to find the right fit.
Groundhog Day (1993)
For some, this Bill Murray and Andie MacDowell rom-com-stuck-on-repeat may feel a little too real right now as we make our way through pandemic sameness, but trust us: there’s a payoff in terms of laughs. Groundhog Day sees an arrogant and egotistical TV weatherman (Murray) try to escape the time loop he’s trapped in while at the same time attempting to woo MacDowell’s character. But as he relives February 2 over and over again, it changes him for the better. Aww.
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