Who does your mind go to when you think of the best rom-com characters of the 1990s?
Is it Vivian Ward going from Hollywood Boulevard to the Regency Beverly Wilshire Hotel in Pretty Woman? Is it Cher Horowitz “totally buggin’” on the Los Angeles freeway in Clueless?
Maybe it’s Phil Connors, stuck reliving Groundhog Day over and over?
Here at Watch With Us, we love the classic ’90s rom-coms and the memorable characters in them who have gone on to become pop culture icons. Here are our five favorite rom-com characters from the 1990s.
5. Annie Reed (Meg Ryan) — ‘Sleepless in Seattle’ (1993)
Sleepless in Seattle follows widower Sam (Tom Hanks), who moves to Seattle with his young son Jonah (Ross Malinger) in the wake of his wife’s death. When Jonah calls into a talk radio program in an attempt to find a new wife for his dad, Sam reluctantly agrees, and little does he know that an engaged reporter named Annie Reed (Meg Ryan), who lives in Baltimore, has suddenly fallen for him.
Sleepless in Seattle is one of the best American rom-coms — written by the great Nora Ephron — and part of what makes it so classic is that Annie’s character is kind of deranged. She becomes so obsessed with this guy on the other side of the country that she flies across the country to spy on him and his son (after having a private detective gather information on him, too). In the end, they end up together, and of course, Annie is charming by virtue of Ephron’s writing and Ryan’s performance.
4. Robbie Hart (Adam Sandler) — ‘The Wedding Singer’ (1998)
After he’s abandoned at the altar by his fiancée, wedding singer Robbie Hart loses all hope that he will ever find someone to love him, and he sinks into a deep depression. However, that all changes when he meets a bride-to-be named Julia (Drew Barrymore), who enlists Robbie’s help in planning her wedding. As the two get to know each other in preparation for Julia’s big day, Robbie starts to fall in love with her — and has to race to win her over before his nuptials.
The Wedding Singer marks the first of three fruitful collaborations between Adam Sandler and Barrymore, who have an undeniable rom-com chemistry. But The Wedding Singer was also notable for the palpable charm of the down-on-his-luck Robbie, a role that avoids the typical Sandler abrasiveness seen in then-contemporaneous comedies like The Waterboy and instead shows a surprisingly mature vulnerability. Robbie ends up embodying characteristics that would come to define many of Sandler’s lauded roles in his later career, in an earnest and sweet performance that still has that Sandler sense of humor.
3. Phil Connors (Bill Murray) — ‘Groundhog Day’ (1993)
On February 2, cynical meteorologist Phil Connors and his weather team travel to Punxsutawney, PA, to cover the annual Groundhog Day festivities that take place in the town. But Phil finds that when he wakes up in his hotel the next day, it’s Groundhog Day all over again. Stuck in a purgatorial time loop, Phil goes through the five stages of grief in accepting his fate, while finding himself falling for his colleague Rita (Andie MacDowell), who can never remember their time together.
Phil Connors is handily one of Bill Murray‘s best roles of his career, in addition to being a legendary rom-com character. The trajectory of Phil’s character development is a rollercoaster experience, as Groundhog Day oscillates between sharp humor and existential drama. Ultimately, the screenplay delivers plenty of laughs while chronicling Phil’s emotional journey from selfish narcissism to self-actualization.
2. Vivan Ward (Julia Roberts) — ‘Pretty Woman’ (1990)
After hiring a sex worker on a whim, businessman Edward Lewis (Richard Gere) finds that the free-spirited Vivian Ward has grown on him, so he decides to hire her to accompany him at a series of social events for the rest of the week. As Vivian struggles to adjust to Edward’s mega-rich lifestyle (just how does one behave at a polo match, exactly?), they find themselves developing an increasingly strong bond that is threatened largely by their dissimilar tax brackets. Can the pair bridge the gap between their worlds?
Pretty Woman is the role that catapulted Julia Roberts into A-list stardom for good reason. The Oscar-winning actress has an irresistible presence throughout the movie, and her Vivian Ward is iconic because of the charm and intelligence she brings to it. The role helped make Roberts an America’s Sweetheart for the ’90s, and Vivian Ward into a rom-com heroine for the ages.
1. Cher Horowitz (Alicia Silverstone) — ‘Clueless’ (1995)
This ’90s favorite is a modernized retelling of Jane Austen’s Emma that is set in high school in Los Angeles and centered on spoiled teen beauty queen Cher Horowitz. A self-professed matchmaker, Cher decides to put her romance skills to the test by finding a beau for awkward new student Tai (Brittany Murphy). However, her plan backfires when Tai becomes more popular than her — proving her disapproving stepbrother (Paul Rudd) right about her misguided intentions.
Clueless is perhaps the ultimate rom-com of the 1990s, with Cher Horowitz the most iconic ’90s rom-com character. Alicia Silverstone’s performance turned a line as simple as “Ugh! As if!” into a Hollywood classic, and her portrayal of Cher is full of memorable line readings like “it does not say RSVP on the Statue of Liberty.” Cher’s ’90s-era outfits are iconic, her unabashed confidence is frequently hilarious, and, more importantly, she goes through a genuinely affecting character journey, proving that even legends are human.
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