Uptown Girls Reminds Us to Connect with Our Inner Child, 20 Years Later

While working as a receptionist at Greenestreet Films, writer Allison Jacobs was struck with inspiration by classic New York films like Annie Hall and Breakfast at Tiffany’s, as well as her own personal nannying experiences. She presented her idea to writers and producers at Greenestreet, who immediately loved her vision of a dead rock star’s daughter fallen from grace after her fortune was stolen from her. Director Boaz Yakin, at the time best known for his 1994 Samuel L Jackson vehicle Fresh, wasn’t the most obvious choice to direct the overtly feminine story, but he connected with the characters and understood the singular style of comedy. Thus, Uptown Girls, the story of party girl Molly Gunn and her uptight little hypochondriac charge Ray, was born. 

It’s past time for Uptown Girls, almost universally panned when it first hit theaters 20 years ago, to be widely reconsidered and celebrated as a Y2K New York City fairy tale. Sure, the plot is far-fetched, and the ending in particular is wrapped up in a nice, convenient little bow, but Uptown Girls is a unique story about what young women can learn from each other. 

Uptown Girls goes to darker emotional places than most other light hearted “chick flicks” of the early 2000s, and features career-best performances from Brittany Murphy and Dakota Fanning, as well as cameos from aughts superstars Mark McGrath and Nas. Uptown Girls was shot by legendary New York City cinematographer Michael Ballhaus, who has also photographed the city for heavyweights like Martin Scorsese and Mike Nichols. In his 3-star 2003 review, Roger Ebert defended the film against its haters, dismissing “all cavils about the movie’s logic and plausibility as beside the point,” asserting that “this is not a movie about plot but about personalities.” Ebert was able to see and hear Molly and Ray as vastly different, but equally emotionally complex characters, in a way that his peers were blind to at the time. 

Molly and Ray’s story is a remarkable one because they are complete personality opposites, yet able to connect with each other on a deeper emotional level than they can with anyone else. As Uptown Girls opens, Molly Gunn (Brittany Murphy) lives a fairy-tale life, in both its idyllic nature and its inherent tragedy. She doesn’t have to work, thanks to her nepo baby trust fund that she’s been cruising on after the unfortunate deaths of her rock star parents in a shocking plane crash. Right off the heels of her 22nd birthday, another tragedy strikes; her manager has run away with her fortune, leaving her penniless. Everyone wants something from the rock star princess, and they’re pretty shameless about it, until she’s destitute. Molly is forced to move in with the only person willing to help—her controlling best friend Ingrid (Marley Shelton)—and take a job as a nanny to our fairy tale’s second princess, Ray (Dakota Fanning). Even though she has no skills and now no money, Molly is determined to stay positive. 

Ray’s life has been touched by tragedy as well: Her father has been in a coma for as long as she can remember, and her mother Roma (Heather Locklear), a high level music executive, hardly gives her the time of day. But when Molly and Ray first meet, it is difficult for them to see their similarities because they are much more defined by their differences. The losses of their parents have affected their lives in two very separate ways. Molly is a mess, and runs her life like a tall child: She has a pet pig named Mu, she naps all the time, her whole apartment screams “health hazard” and she has a very sparing grasp on finances. 

Ray, on the other hand, is a tiny adult in ballet clothes. “Precocious” is not a strong enough word to describe Ray’s behavior. She’s beyond vigilant about germs, she exclusively listens to classical music and she seems perfectly capable of running her own life without Molly around. Molly constantly greets the world with a naive optimism, while Ray is already jaded at age eight; “It’s a harsh world,” sounds more like the motto of a weathered divorcee, not a private elementary school kid. Molly can’t believe that Ray has never been to Disneyland. “Alert the media,” is Ray’s caustic response. 

Molly’s unflagging brightness and Ray’s grim cynicism are both completely earnest reactions to having been pushed into a position where they must parent themselves throughout childhood, and into young adulthood, in Molly’s case. Molly has chosen to never grow up, postponing adulthood for as long as possible, whereas Ray grew up too fast. What makes Uptown Girls so compelling is watching Molly parent her own inner child through parenting Ray, which comes to a head in the infamous Coney Island spinning teacups scene.

Ray runs away from home, and Molly is the only one who knows to find her: Sitting in a spinning teacup, which normally would be beneath Ray’s sophisticated sensibilities. Sitting in her little teacup, it is the first scene in which Ray actually looks like a child, helpless and alone. Without speaking, the girls are able to put aside their squabbling to connect through their grief as they spin in a dizzying, beautiful moment.  

Since this is a fairy tale, there is a romantic subplot, but he’s a social climbing, East Village dirtbag instead of Prince Charming. As she desperately clings to her old life, Molly falls for Neal (Jesse Spencer), an up-and-coming musician interested in her only for her dead dad’s sick guitar collection. He doesn’t return Molly’s calls, and has no qualms about using Molly for both style and musical inspiration. In a scene that undoubtedly takes Uptown Girls out of the kids movie zone, Neal even sleeps with Ray’s mom to get ahead in the biz. 

In the end, we are expected to swoon as Neal plays “Molly Smiles,” the smash single written by Molly’s dad, and Ray freestyles at her dance recital. Personally, I haven’t forgiven him, in the same way I hold a grudge against a guy who did my friend dirty—the Grand Gesture is sometimes not enough to win me over, and it certainly isn’t here. Neal slept with Ray’s mom. Now he’s performing at Ray’s dance recital and I’m supposed to think that’s cute? My main criticism of Uptown Girls is the overwhelming kindness the film shows to Neal in the end.

Frustratingly, a lot of the negative reviews do not take umbrage with the too-neat ending, instead choosing to mainly take shots at Brittany Murphy and Dakota Fanning. Stephen Holden wrote in his negative NYT review that Murphy “lacks the innate likability factor,” which we can all agree is utterly ridiculous. Not only did Murphy exude likability in spades for her whole career, but even if she didn’t, why should it matter? Holden simply dismissed Uptown Girls as “shallow,” but some critics took their misogyny even further. 

Michael Dequina disliked Fanning’s performance so much that his review for The Movie Report reads “I don’t advocate child abuse, but Dakota Fanning is a pretty strong argument for it.” Toronto Star critic Geoff Pevere wrote the film off completely without fully paying attention, rhetorically wondering if “two overly pampered but fundamentally lonely persons of the blonde female persuasion [can] bond meaningfully with each other while shopping?” First of all, what does hair color have to do with anything? If Molly and Ray had been brunettes, would that improve or somehow change the meaning of the film? And secondly, there are no such scenes of Molly and Ray bonding while shopping. 

While not the only contemporary critic to be positive on the film, Ebert was able to see beyond the glitzy surface, bravely standing apart in his refusal to rely on gender bias to express disapproval of a film. Maybe the most significant thing Ebert praised about Uptown Girls was its performances; specifically, he compared Murphy’s comedic talents to those of Lucille Ball. “Molly Gunn is a comic original, vulnerable and helpless, well-meaning and inept, innocent and guileless…Murphy’s performance has a kind of ineffable mischievous innocence about it.” 

Indeed, one could imagine a scene in I Love Lucy where Lucy attempts to get a job at a luxury bedding store, and consequently falls asleep on one of the beds, as Molly does in Uptown Girls. Murphy’s face is pure Ball as she realizes (too late) that she’s about to get smacked in the face with a swinging door, in a moment where she needed to look particularly dignified. Thankfully, Ebert was able to recognize that an actress’ performance should not be judged solely on “likability,” but on its more palpable merits, such as comedic timing and vulnerability. Ebert was also more favorable than most critics toward Fanning’s performance. He wrote that “Ray does seem prematurely old…in the case of Dakota Fanning, I think we are looking at good acting.”

Uptown Girls might still not be taken seriously today by the larger community of serious film critics and historians, but the film has found its audience of lonely young women trying to find their place in the world. If you search “Uptown Girls” on social media, you’ll find a sea of girls posting about their emotional connection to the film, and of course, their love of Murphy’s performance. Some of this could very well be written off as 2000s nostalgia, but a lot of love for Uptown Girls comes from a place of deep sadness, both for the girls that we once were and the girls we could have been. 

Y2K trends in fashion, music and even film have yet to go out of style, because they are material ways for young adult women to connect with their inner child. A woman sporting sparkly hair clips with colorful denim overalls, walking down the street blasting Britney Spears out of chunky headphones, might look silly to an outsider, but fellow Y2K baddies are able to recognize a woman who listens to and respects the girl inside. Watching Uptown Girls has a similar effect, and not only because of Molly Gunn’s “rock star’s daughter” wardrobe; it is 2000s nostalgia, yes, but with a distinctly feminine, emotionally therapeutic purpose. Every time I hear the Mitski lyrics “And I was so young when I behaved 25 / Yet now I find I’ve grown into a tall child,” I think of Molly and Ray, sadly spinning around and around in those teacups. 

Brooklyn-based film writer Katarina Docalovich was raised in an independent video store and never really left. Her passions include sipping lime seltzer, trying on perfume and spending hours theorizing about Survivor. You can find her scattered thoughts as well as her writing on Twitter.