Buena Vista/courtesy Everett Collection, PRW 058, Photo by: Everett Collection (51981)
People act like rom-coms are just a guilty pleasure, but the reality is everyone loves rom-coms, so how guilty can they be?
Hulu’s rom-com library in particular is a great place to look for some of the best of the best. They’ve got picks from the 20th century to the past five years, with stars like Julia Roberts and Meryl Streep.
This February, Watch With Us has added two beloved classics to our list of Hulu rom-coms. Our first pick is Pretty Woman, the ’90s staple that served as the breakout for Roberts.
We also picked the Shakespeare-inspired teen romance 10 Things I Hate About You.
Need more recommendations? Then check out the Best New Movies on Netflix, (HBO) Max, Hulu, Amazon Prime and More, the Best Movies on Amazon Prime Video Right Now, and the Best Rom-Com Movies on Netflix Right Now.
‘Pretty Woman’ (1990)
While on a work trip to Los Angeles, businessman Edward Lewis (Richard Gere) meets sex worker Vivian Ward (Julia Roberts) as he struggles to operate his rental stickshift car. After Julia drives Edward to his hotel, the two end up spending the night together, and their chemistry brings about a strange arrangement: Edward wants to pay Vivian $3,000 to stay with him for the week. But when their professional arrangement develops into something more, the vast differences in the worlds they come from prove to be significant hurdles.
Some aspects of Pretty Woman haven’t aged well — like that tired trope of “the hooker with a heart of gold.” However, the film manages to transcend some of its clichés by the sheer charismatic weight of Roberts’ performance, her chemistry with Gere and its infectious screwball comedy. Ultimately, the movie is a fun, lighthearted caper and the perfect kind of escapist fantasy.
’10 Things I Hate About You’ (1999)
This modernized take on Shakespeare’s The Taming of the Shrew stars Julia Stiles as abrasive but intelligent teenager Kat Stratford. It’s this acerbic personality that keeps the boys away from Kat, which is a problem for her younger sister, Bianca (Larisa Oleynik), who isn’t allowed to date anyone until Kat has a boyfriend first. When new student Cameron (Joseph Gordon-Levitt) falls desperately for Bianca, he schemes to get handsome bad boy Patrick (Heath Ledger) to date Kat and get around their father’s (Larry Miller) overprotective rule.
While Kat’s brand of feminism was seen by some as “extreme” at the time, her character is now regarded as a refreshing subversion of female expectations and a progressive take on typical high school movie stereotypes. This unconventional approach has allowed 10 Things I Hate About You to endure as one of the best romantic comedies ever. It’s mature and emotionally resonant, yet still manages to be funny.
‘My Big Fat Greek Wedding’ (2002)
The sprawling but tight-knit Portokalos family worries for Toula (Nia Vardalos), who is still unwed at 30 years old. That all changes when Toula meets Ian Miller (John Corbett), a handsome teacher who is, distressingly, not Greek, but causes Toula to fall in love with him. While Toula struggles to get her overbearing, judgmental family to accept Ian (as their wedding fast approaches), Toula also learns more about her own cultural heritage and identity as a Greek American woman.
Big-hearted, winsome and with a cast that embodies a wide array of eccentricities, My Big Fat Greek Wedding is a beloved and enduring rom-com for its relatable themes pertaining to family, its gentle humor and its exploration of embracing one’s cultural roots.
‘Maggie’s Plan’ (2016)
A single woman named Maggie Hardin (Greta Gerwig) is attempting to conceive a child on her own with a sperm donor and raise it as a single mom. However, her plans get derailed when she ends up falling for a married man, John Harding (Ethan Hawke). When their affair destroys John’s marriage, the two end up getting married, but Maggie can’t shake the feeling that John was meant to be with his first wife (Julianne Moore) all along.
This smart, subversive rom-com is led by a typically winsome performance from Gerwig, whose character is involved in a compelling love triangle that constantly surprises you. Maggie’s Plan is a humorous riff on modern relationships and life plans gone awry that blends smart, funny writing with surprising poignancy. The excellent supporting cast includes Bill Hader, Maya Rudolph and Wallace Shawn.
‘When Harry Met Sally’ (1989)
College graduates Harry Burns (Billy Crystal) and Sally Albright (Meg Ryan) meet in 1977, and on a long car ride from Chicago to New York City, they debate whether men and women can remain platonic friends. Over the course of twelve years, Harry and Sally continue to find one another through chance encounters, and while their friendship grows, so do romantic feelings. However, Harry is determined not to let his attraction ruin things.
With a sharp screenplay written by the great rom-com writer Nora Ephron, When Harry Met Sally handily shines as one of the best romantic comedies ever made. Crystal and Ryan sport an irresistible comedic and romantic chemistry that has stood the test of time, and the warmly touching narrative will sneak up on you, leaving you grasping for a tissue box by the very end.
‘Plus One’ (2019)
Ben (Jack Quaid) and Alice (Maya Erskine) have been friends since college and are now in their late twenties, navigating the reality of everyone around them getting married. With Alice having recently left a relationship and Ben getting rebuffed by his crush, the pair agree to be each other’s permanent wedding dates during a particularly busy summer of weddings. Of course, the two unlucky-in-love singles find their platonic wedding dates becoming something more as the summer goes on.
Critics felt that Plus One managed to breathe new life into the romantic comedy genre, with fresh faces like Quaid and Erskine who balance the heart and the humor with ease. Their well-matched chemistry, in addition to the film’s buoyant narrative and emotional stakes, makes Plus One a fantastic recent entry into the rom-com canon. Plus One both embraces and subverts genre expectations, creating something that’s both new and familiar.
‘She’s the Man’ (2006)
There’s nothing like a modern-day Shakespeare adaptation, right? Something about the bard’s timeless stories being cleverly transposed into our world makes you go, “Aha!” whenever you recognize a reference. This reimagining of Twelfth Knight follows Viola Hastings (Amanda Bynes), who disguises herself as her twin brother Sebastian to join the boys’ soccer team at Illyria Prep after her own team is cut. The story takes a turn when Viola, masquerading as Sebastian, finds herself falling for her roommate, Duke Orsino (Channing Tatum).
The comedic talents of Tatum and Bynes are on full display in this hilarious high school comedy about coming of age and having greatness thrust upon you. There’s also some great tips on flirting — for example, you can always ask the object of your affections if they like cheese!
‘It’s Complicated’ (2009)
A rom-com about divorce? It works better than you’d expect. Jane (Meryl Streep) and Jake (Alec Baldwin) have been divorced for decades. But when a celebratory drink after their son’s graduation turns into an unexpected hookup, they find themselves beginning an affair. To make matters worse, Jake is married to the woman he cheated on Jane with (Lake Bell), while Jane has just started seeing a sweet architect named Adam (Steve Martin).
It’s a love square that’s as tangled and tumultuous — and full of hilarious miscommunications — as can be. Nancy Meyers directs this witty and nuanced comedy, which lives up to her reputation for telling funny and emotional stories against gorgeous backdrops.
‘Sleeping with Other People’ (2015)
Directed by Leslye Headland of Russian Doll, Sleeping with Other People shares a similarly twisted sense of humor. It follows Jake (Jason Sudeikis) and Lainey (Alison Brie), two New Yorkers who first met in college during a one-night stand. Over a decade later, their paths cross again at a support group for sex addiction, and they decide to become platonic friends.
Each helps the other navigate their romantic pitfalls, without realizing they’re falling in love along the way. Sleeping with Other People is honest, full of relatable emotional entanglements and hilarious performances from Brie, Sudeikis and the supporting cast.
‘The Broken Hearts Gallery’ (2020)
This underrated rom-com had the misfortune of being lost in the shuffle of 2020 movie releases due to the COVID-19 pandemic, but it stars the fabulous Geraldine Viswanathan (Thunderbolts*, Blockers) and Dacre Montgomery (Stranger Things) as unlikely collaborators on an unusual art project. Lucy (Viswanathan) is fired from her assistant job at a New York art gallery on the same night as a brutal breakup, leaving her heartbroken over her ex. Unable to part with the mementos of her lost relationship, Lucy decides to create a space where people can leave memorabilia from past relationships—essentially a gallery of broken hearts.
It just so happens that Nick (Montgomery) is looking for a gimmick to save his failing boutique hotel. Together, they create a place where people can display their keepsakes from breakups past. The publicity for their Gallery of Broken Hearts gets hot — and so does the chemistry between the two leads.
The Broken Hearts Gallery has a witty script, a diverse cast and a real insight into the experience of heartbreak. Don’t break our hearts by skipping this movie.
‘No Hard Feelings’ (2023)
No Hard Feelings is one of those comedies where the premise is deeply disturbing, but the great writing and talented cast sell it so well that you find yourself laughing anyway. In this romantic comedy, down-on-her-luck waitress Maddie (Jennifer Lawrence) is facing bankruptcy after having her car repossessed. Desperate for a new car, she answers an unusual Craigslist ad posted by wealthy parents Allison and Laird Becker (Laura Benanti and Matthew Broderick).
The Beckers are worried about their 18-year-old son Percy (Andrew Barth Feldman) starting college in the fall, as he is shy, awkward and inexperienced. So they hire Maddie to “date” Percy, without giving him any idea what’s happening. (See? Told you it was disturbing.)
But as Maddie’s over-the-top attempts to seduce Percy turn into a real friendship, Maddie begins to open up about her complicated past while Percy learns to stand on his own two feet. There’s hilariously shocking physical comedy (a naked fist fight occurs — we won’t reveal the participants) and a warm sweetness that will move and surprise you.
‘Palm Springs’ (2020)
Andy Samberg (Saturday Night Live, Brooklyn Nine-Nine) and Cristin Milioti (How I Met Your Mother, The Penguin) star in the genre-bending romantic comedy Palm Springs. While attending a wedding in Palm Springs, Nyles (Samberg) and Sarah (Milioti) get stuck in a time loop, forced to relive the day of the wedding over and over again. Meanwhile, another wedding guest named Roy (J.K. Simmons) blames Nyles for being trapped in the time loop as well and is constantly seeking revenge by killing him (which resets the loop).
As Nyles and Sarah grow closer, secrets about their lives before the wedding are revealed. Will they be able to move forward together, or will they stay stuck in the past? Milioti and Samberg are charming and funny actors with great chemistry, and you’ll find yourself rooting for them despite their flaws. Palm Springs feels like the perfect millennial interpretation of Groundhog Day.
‘Fire Island’ (2022)
A modern-day retelling of Pride and Prejudice, Fire Island follows a “found family” of gay men who take a summer trip to the titular island every year. When Howie (Bowen Yang of Saturday Night Live fame) meets the rich and charming Charlie (James Scully) at a party, Howie’s best friend Noah (Joel Kim Booster, who also wrote the film), is determined to get them together. But Charlie’s judgmental friend Will (Conrad Ricamora, who is adorably dorky in the “Mr. Darcy” role) seems to get in the way at every turn.
The movie shows how wealth and social class can still come into play in present-day relationships, while maintaining the original story’s themes of miscommunication and first impressions. The supporting cast is hilarious and includes Margaret Cho and Yang’s Las Culturistas co-host Matt Rogers.
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