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Richard Gere and Julia Roberts in Pretty Woman
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When Romance Met ComedyWhen Romance Met ComedyWith When Romance Met Comedy, Caroline Siede examines the history of the rom-com through the years, one happily ever after (or not) at a time.

If you want a marker of just how iconic Pretty Woman is, consider that the film contains at least four or five different outfits one could wear as instantly recognizable Halloween costumes. That’s a pretty impressive track record for any film, let alone a contemporary romantic comedy. In fact, when it comes to sheer volume of iconography, I’m not sure anything else in the genre has Pretty Woman beat. From Julia Roberts singing in a bathtub and laughing at a snapped jewelry box to Richard Gere climbing a fire escape, bouquet in hand, Pretty Woman is one of the most oft-referenced and -parodied romantic comedies ever. It’s the sort of film that feels built into our cultural DNA, not just as a piece of cinema but also as a touchstone for the heartwarming feelings invoked by an entire genre.

That’s because Pretty Woman was fundamental in shaping what we think of as the modern romantic comedy. The one-two punch of When Harry Met Sally in 1989 and Pretty Woman in 1990 kicked off what was then considered a rom-com renaissance, and which we now consider to be the genre’s heyday. Those two films established two distinct templates for romantic comedies. When Harry Met Sally is a low-key, relatively realistic hangout comedy where the only thing standing in the way of the two protagonists finding love is their inability to realize they’re perfect for each other. Pretty Woman, meanwhile, relies on a more high-concept premise and is overtly positioned as a modern-day fairy tale.

Those templates already existed (in the 1980s, it was the Moonstruck/Overboard dichotomy), but When Harry Met Sally and Pretty Woman solidified them for the modern era. Both films were critical and commercial hits, and both garnered Oscar attention—a Best Original Screenplay nomination for Nora Ephron’s When Harry Met Sally script and a Best Actress nod for Julia Roberts. Pretty Woman, in particular, was a box office smash. It grossed $178.4 million domestically (contributing to a worldwide gross of a whopping $463.4 million) on just a $14 million budget. At the time, it was the highest-grossing romantic comedy ever produced and still tops the rom-com charts in terms of number of tickets sold. Pretty Woman proved romantic comedies could be major players at the box office, which, more than anything, probably contributed to the genre’s dominance in the ’90s and early 2000s.

Which is appropriate because Pretty Woman is a film that’s obsessed with money. In fact, the first line of dialogue we hear is, “No matter what they say, it’s all about money.” Pretty Woman is a riff on both the classic Cinderella tale and George Bernard Shaw’s Pygmalion, but one where the female protagonist has more agency over her class-climbing narrative. In place of magically gifted slippers and old British men making bets, Julia Roberts’ vivacious sex worker, Vivian Ward, negotiates her own deal to upward mobility. For $3,000 she agrees to spend the week as a no-strings-attached, full-service escort to Richard Gere’s Edward Lewis, a charismatic but emotionally detached “corporate raider” on a business trip to L.A. After their quirky first meeting—Edward initially picks up Vivian on Hollywood Boulevard just to ask for directions—one of the first things they bond over is their business-first approach to life. “I never joke about money,” Vivian notes. “Neither do I,” Edward responds.

Pretty Woman isn’t subtle about drawing parallels between Vivian and Edward. “You and I are such similar creatures,” he muses. And just in case we miss the point, he adds, “We both screw people for money.” Vivian and Edward each have strict policies about separating emotions from business—him because of some dead-daddy issues (i.e., his heart is too small) and her because she doesn’t want to fall for any of her clients (i.e., her heart is too big). Naturally, that means they’re perfect for each other, but they can’t acknowledge that because the business deal that brings them together is also the thing that winds up standing between them and Vivian’s “Cinder-fuckin’-rella” dreams.

Particularly at the time of its release, and sometimes even still, Pretty Woman has been accused of glamorizing prostitution. Given how complex and multifaceted an issue that sex work is, it’s certainly fair to say that this fairy tale rom-com doesn’t exactly offer a nuanced exploration of the topic. But rewatching the film today—in an era in which supporting the agency of sex workers has become a more mainstream feminist position—it holds up better than you might expect. Pretty Woman acknowledges that sex work can be dangerous (early on, Vivian stumbles upon a crime scene where a dead sex worker has been found in a dumpster), and it acknowledges that it’s not the path Vivian and her roommate, Kit (a scene-stealing Laura San Giacomo), originally wanted for their lives. But it’s not judgmental of their work either. Vivian and Kit proudly live by the motto, “We say who, we say when, we say how much.”

Most refreshingly, Pretty Woman depicts Vivian and Kit’s friendship as something that’s hugely positive for both of them, not an example of the depraved world Vivian has to leave behind on her journey to self-actualization. Again, there are other, better explorations of sex work, even within a rom-com context. Those include the British TV show Secret Diary Of A Call Girl and FX’s Pose, which isn’t exactly a rom-com, but which features a storyline that feels like a purposeful deconstruction of the Pretty Woman narrative as told through the lens of a black transwoman. Still, in terms of social commentary via fairy tale storytelling, Pretty Woman isn’t the disaster it might have been.

It’s not perfect either. There’s something vaguely patronizing about the way the film depicts Vivian’s accession to the upper crust. She’s a bit of a Cool Girl stereotype to begin with—knowledegable about cars and uncouth, but only in a cute way. Her “no kissing on the mouth” rule feels like a cutesy Hollywood quirk, and the “she’s emotionally moved by opera so she has value as a human being!” sequence has a particularly condescending edge to it. It was producer Laura Ziskin who attempted to give the film more of a feminist twist by pushing for a final line about the fact that Vivian rescues Richard as much as he rescues her. Yet Pretty Woman doesn’t quite sell its “they both changed each other for the better” message when we spend so much time watching Edward critique Vivian’s behavior, while she just kind of vaguely inspires him with her presence. It also doesn’t help that—for as much laidback charisma that Gere brings to the role—Edward is kind of a dud of a character.

Edward was even more unlikable in J.F. Lawton’s original script for Pretty Woman, which was titled 3,000 (in reference to Vivian’s fee for the week) and written to be a grittier cautionary tale inspired by films like Wall Street. Vivian was a cocaine addict, and one of Edward’s requirements was that she stay off drugs for the week. In the end of the original, Edward and Vivian don’t wind up together. He drops her back on Hollywood Boulevard and literally tosses her money into the gutter. The script ends with Vivian and Kit using the money to take a despondent trip to Disneyland.

It was director Garry Marshall who saw within that script a lighter version of the story that positioned Vivian as Rapunzel, Richard as Prince Charming, and hotel manager Barney Thompson (an incredibly endearing Héctor Elizondo) as the fairy godmother. Lawton, who retains sole screenwriting credit, was more than happy to reimagine the project to suit the “incredible pop instincts” of Mr. Marshall. Already a legendary creative force in TV, Marshall had waded into the rom-com waters a few years prior with the Goldie Hawn/Kurt Russell vehicle Overboard. But it was Pretty Woman that made him a major rom-com creative force, which he would continue to be throughout the rest of his career—including helming the 1999 Roberts/Gere reunion vehicle, Runaway Bride. Thanks to Marshall’s light touch and eye for commercial appeal, Pretty Woman is an endlessly watchable film. It’s funny without losing its emotional groundedness, high-stakes without losing its charm, and sexy without losing its romantic innocence.

Having gotten his big break playing a sex worker in 1980’s American Gigolo, Gere was on the other side of the table (or, rather, bedroom) as Roberts launched her own career with an instant star-making turn. Pretty Woman premiered just three days before Roberts attended the 1990 Oscars as a Best Supporting Actress nominee for Steel Magnolias, making it quite the week for the emerging 23-year-old star. Along with Meg Ryan, Roberts helped define the rom-com leading lady of the modern era: sweet, smart, self-possessed, and endearingly quirky.

Roberts is phenomenal in Pretty Woman in all the ways that are usually cited— her guileless persona, infectious laugh, million-dollar smile, keen sense of comedic timing. Less appreciated, however, is her ability to give Vivian a complex inner life beneath her exterior charms. When Edward’s sleazy lawyer, Philip Stuckey (Jason Alexander), starts cruelly objectifying her, Vivian immediately slips into self-preservation mode, feigning politeness while trying to shrink herself down to get away from him. It’s a painfully relatable piece of physical acting for anyone who’s ever deployed similar tactics to escape sexual harassment. Pretty Woman is at its most nuanced in exploring the betrayal Vivian feels toward Edward for casually revealing her job to his friend. Unfortunately, Stuckey’s mostly just there to make Edward look better by comparison, and his violent attempt to rape Vivian is largely played as a big hero moment when Edward gets to rescue her.

Ultimately, Pretty Woman is a little bit too enamored with wealth to meaningful critique the world of the wealthy. The chemistry between Roberts and Gere is timeless, but Pretty Woman is definitely rooted in the tail end of the “greed is good” ethos of the 1980s. Tellingly, the film’s most emotionally satisfying scene isn’t about romance; it’s about money. “Big mistake. Big. Huge!” a newly re-styled Vivian gets to gloat at the snooty saleswoman who refused to help her when she came in wearing her street clothes. Yet there’s also something kind of refreshing about a rom-com that openly acknowledges its characters’ wealth, rather than pretending that fancy hotel rooms and swanky clothes are simply the norm. Vivian’s big makeover comes only after Edward takes a store manager aside, promises they’re about to spend “an obscene amount of money,” and openly demands the sucking up that comes with it. (Cue the hilarious line in Romy And Michele’s High School Reunion, “I just get really happy when they finally let her shop.”)

In the end, Pretty Woman is an unabashedly commercial film made by a director with a keen knack for knowing just what audiences want. Personally, I think the better Julia Roberts rom-com, and the more interesting Julia Roberts rom-com performance, is My Best Friend’s Wedding. And in terms of Garry Marshall films, my heart belongs to The Princess Diaries. But it’s unlikely that either of those films would’ve come to fruition if Pretty Woman hadn’t paved the way first. In telling the story of one woman pursuing her fairy tale happy ending, Pretty Woman created its own fairy tale success story that romantic comedies have been trying to recreate ever since.

Next time: Revisiting Eddie Murphy’s underappreciated Boomerang.

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About the author

Caroline Siede

Contributor, The A.V. Club. Caroline Siede is a pop culture critic in Chicago, where the cold never bothers her anyway. Her interests include superhero movies, feminist theory, and Jane Austen novels.