If you haven’t been able to tell, the Watch With Us team loves rom-coms.
But if you don’t love romantic comedies, it’s safe to say you probably don’t have a heart — or you just haven’t watched a good rom-com yet. There are a lot of bad ones, after all.
Without a doubt, the best decade for rom-coms was the 1990s.
Cher Horowitz was playing matchmaker, Vivian Ward was becoming a pretty woman and Phil Connors was getting stuck in a time loop for eternity.
So, turn back the clocks with us and look back on the best romantic comedy from every year of the 1990s.
1990: ‘Pretty Woman’
Businessman Edward Lewis (Richard Gere) hires a sex worker named Vivan Ward (Julia Roberts) to help him drive his stick-shift rental car, and he finds that her infectious and free-spirited personality has grown on him. While on his business trip in Vegas, Edward decides to hire Vivian to join him at work events for the rest of the week. Vivian struggles to adjust to Edward’s upper-class sensibilities, but they find themselves falling for one another. But can they manage to bridge the divide between their different worlds and make a real romance work?
Pretty Woman turned Roberts into an A-list movie star overnight through her utterly fetching performance, bringing charm, humor and intelligence to the role. While the movie indulges in the “hooker with a heart of gold” stereotype, it’s undeniable that Pretty Woman is a romantic film that stands in stark contrast to more cynical fare of the ’90s. In the end, Pretty Woman is light-hearted, tender, funny and pure escapism.
1991: ‘Defending Your Life’
After Daniel Miller (Albert Brooks) gets hit by a bus and dies, he arrives in the afterlife to discover that he hasn’t gotten to heaven, but instead a purgatorial realm where he must stand trial and defend the actions of his time on Earth. If he successfully defends his life, he will ascend to a higher plane of existence — if he fails, he’ll be sent back to Earth reincarnated. While awaiting his judgment, he meets a woman named Julia (Meryl Streep), who seems to have had a perfect life on Earth, and as they fall deeper in love, Daniel questions whether he’ll win his trial.
Defending Your Life is both hilarious and heartstring-tugging, a comfort movie that is also intelligent (and might make you feel more comforted by the notion of death). The performances from Brooks and Streep are fantastic, as the two actors display a warm and authentic chemistry with one another. Ultimately, Defending Your Life is a top-tier feel-good movie that addresses deep philosophical questions with a gentle touch.
1992: ‘Boomerang’
After a company merger, arrogant ad executive Marcus (Eddie Murphy) suddenly finds himself working under the headstrong Jacqueline (Robin Givens). Not only are his ideas about gender in the workplace challenged, but also his ideas about dating, as his ladies’ man reputation meets its match against Jacqueline’s similarly cavalier attitude to men. When the two become sexually intimate, Marcus finds himself getting a taste of his own medicine — and he doesn’t like it. At the same time, Marcus becomes torn between Jacqueline and a pretty friend-of-a-friend named Angela (Halle Berry).
Boomerang may have polarized critics at the time, but it has gone on to be viewed as an underappreciated rom-com classic. While the plot is a bit predictable, the stars and the sense of humor make it an exceedingly entertaining experience, and some believe that it holds up better than other rom-coms of the same period. Its iconic cast and witty storyline are completely delightful.
1993: ‘Groundhog Day’
Weatherman Phil Connors (Bill Murray) is a cloud of negativity as travel with his television team to Punxsutawney, Pennsylvania, in order to cover the upcoming festivities for Groundhog Day. When a blizzard strikes on the holiday, Bill is living his worst nightmare, trapped in Punxsutawney — but when he wakes up the next day, it seems his nightmare is never-ending. With his life suddenly stuck in a time loop reliving February 2 over and over, Phil goes through the five stages of grief as he copes with his imprisonment and slowly falls for his new producer, Rita (Andie MacDowell)
Groundhog Day is a sharp and philosophical romantic comedy that is one of Murray’s very best, and also the last comedy collaboration between the legendary actor and co-writer and director Harold Ramis. While the film is undeniably hilarious, the movie does an excellent job of combining riotous humor and poignant drama.
1994: ‘Four Weddings and a Funeral’
Perpetually single Charles (Hugh Grant) has great company with his group of friends who are all equally unlucky in love. However, Charles ends up meeting a beautiful American girl named Carrie (Andie MacDowell) by chance at a wedding, and suddenly it seems that maybe Charles’ luck has changed for the better — until she heads back home to the U.S. But then, Charles and Carrie’s paths continue to cross at weddings (and one funeral) and though the timing never seems right, Charles can’t help but shake the feeling that it’s meant to be.
The low-budget success of Four Weddings and a Funeral was a huge surprise, and it ended up becoming the highest-grossing movie in British film history at the time — it even received an Academy Award nomination for Best Picture. The movie cements Grant’s status as rom-com leading man material, and it is overall a deeply enchanting experience that is funny without being overly mawkish. Still, it’ll tug on your heartstrings in all the right ways.
1995: ‘Clueless’
Popular teen beauty queen Cher Horowitz (Alicia Silverstone) fancies herself a matchmaker, and she decides to put her skills in the romance department to the ultimate test by finding a mate for the tomboyish and awkward new student Tai (Brittany Murphy). But in Cher’s quest to make Tai dateable, she ends up unintentionally making her more popular, which only proves her ex-stepbrother Josh (Paul Rudd) right in his views that she is self-absorbed and misguided in her intentions towards others.
Clueless is handily one of the best romantic comedies of all time — and a surprisingly great adaptation of the classic Jane Austen novel, Emma. The film basically has everything you need to be an iconic movie: littered with memorable lines, outstanding performances and still-fashionable clothes, in particular, the outfits worn by Cher and her best friend Dinne (Stacey Dash). Clueless is also a sharp satire of Beverly Hills culture in addition to other teen comedies of the time period.
1996: ‘Jerry Maguire’
Successful sports agent Jerry Maguire (Tom Cruise) has an epiphany after an experience with a player and his injured son. Fed up with the dishonesty and indifference in his business, he pens an earnest company-wide memo that immediately gets him fired. With only one of his clients (Cuba Gooding Jr.) remaining in his roster, Jerry starts his own management company with single mother Dorothy Boyd (Renée Zellweger) joining him. As Dorothy and Jerry struggle to make the business a success, they slowly fall for one another.
This sports rom-com charmer seamlessly blends humor, heart, romance and sports drama into an enduring American classic. Cruise confidently leads his story of personal redemption in a film with a great message about prioritizing integrity and human compassion over corporate greed. If you haven’t seen it, you’ll probably still recognize the movie’s many iconic lines, such as “Show me the money!” and “You complete me.”
1997: ‘My Best Friend’s Wedding’
Julianne Potter (Roberts) and Michael O’Neal (Dermot Mulroney) made a deal when they were kids that if they were still single by age 28, they’d marry each other. But four days before Julianne’s 28th birthday, Michael announces that he’s set to marry the 20-year-old Kimberly (Cameron Diaz). Suddenly, Julianne realizes that her bet with Michael wasn’t just a silly joke — it was real, and she really loves him. Julianne sets her sights on stopping the wedding, until her appointment as maid of honor makes this task much more difficult.
After Roberts catapulted herself to being Queen of the Rom-Coms with her performance in Pretty Woman, she continued to charm audiences with My Best Friend’s Wedding. As ever, Roberts delivers her lines with an effortless charisma, smiling and crying with equal amounts of authenticity. Overall, My Best Friend’s Wedding manages to be a refreshing and subversive spin on the rom-com genre that is peppered with ingenious comedic scenes that will have you in stitches.
1998: ‘There’s Something About Mary’
Teenager Ted Stroehmann (Ben Stiller) is about to head to prom with Mary Jensen (Diaz), but an embarrassing incident at her house keeps him from going. Years later, Ted still views Mary as “the one who got away,” so he hires P.I. Pat Healy (Matt Dillon) to find her so he can finally get his second chance. But Ted never expected that Pat would fall for Mary too, and when Ted sets off to find her himself, he finds himself up against both Pat and another man who can’t help but fall for Mary’s charms.
There’s Something About Mary blends low-brow humor with a surprisingly genuine heart, and the movie succeeds in its ambitious tonal balance of dipping back and forth between ridiculous, gross-out, silly gags and a tender, affecting love story. Every comedic performance in the film is firing on all cylinders, and the narrative keeps you constantly entertained. The sequence in which Mary unknowingly has an “unwanted substance” in her hair is one of the most iconic rom-com moments of all time.
1999: ’10 Things I Hate About You’
Beautiful but abrasive teenager Kat Stratford (Julia Stiles) is the only thing getting in between her sister Bianca (Larisa Oleynik) being able to have a boyfriend. Due to their father’s (Larry Miller) regressive rule, Bianca can only start dating once her sister does, and the only thing Kat does with boys is scare them away. When new kid Cameron James (Joseph Gordon-Levitt) becomes smitten with Bianca, he attempts to devise a plan to get bad boy Patrick Verona (Heath Ledger) to ask Kat out.
Based loosely on William Shakespeare’s The Taming of the Shrew, 10 Things I Hate About You is more than just a rom-com adaptation of classic literature. The movie has been hailed as a strikingly feminist take on the archetypal high school comedy, successfully subverting tropes and finding a strong, feminist lead character in Kat. The film’s unconventional nature and still-rockin’ late ’90s soundtrack have allowed it to endure as one of the best rom-coms of all time.
