Every day until Valentine’s Day, Entertainment Weekly is celebrating our special romantic comedy-themed Untold Stories issue. Check out all of our behind-the-scenes tidbits, reunions, and oral histories — and follow #LoveEWstyle on Twitter and Instagram.
No rom-com is complete without an epic makeover and it truly takes a village: from the director to the costume designer to the music supervisor (can you even think of the words Pretty Woman without hearing Roy Orbison’s signature croon?). We talked to those behind the most memorable transformations, so get ready to swipe that plastic, primp, and preen as we look back at some of the best romantic comedy makeovers of all time.
The Breakfast Club (1985)
The Basket-Case becomes the Princess. Near the conclusion of John Hughes’ seminal teen movie The Breakfast Club, Ally Sheedy’s Allison receives a makeover at Claire’s (Molly Ringwald) hands that makes Andrew (Emilio Estevez) sit up and ask, “What happened to you?”
For most of the film, Allison wears oversized, dark clothing. Costumer Marilyn Vance made all of Allison’s looks, including her anorak, black sweater, and patterned skirt. “She wants to disappear; she doesn’t feel loved. Therefore, she is just a black, empty space,” Vance says of Sheedy’s initial style. With Claire’s assistance, Allison pulls her hair back from her face with a frilly white ribbon and suddenly emerges fresh-faced in a soft pink blouse.
Vance says there was originally a lot more to the makeover. “All you got was, they go into the bathroom and she pulls out the stuff, and the next you thing you know she’s wearing it,” says Vance. Hughes and Vance had conceived of Allison being a softer, more feminine girl underneath her gruff exterior. “Underlying all of that negativity that she puts out is this lovely girl who’s just afraid of life,” says Vance. Allison obscured her true self, literally keeping it under wraps. “[The blouse] is in that purse that we made for her,” she says. “She had all her delicate things that she liked [in there], but they never emptied her purse. The whole idea was that she was wearing it under all that horrible stuff. She had things in her bag.”
Subtlety in color and makeup was key to the transformation, and Vance bemoans the more abrupt jump in the final cut that makes it feel like Allison needed to become more beautiful to merit attention. “That last part wasn’t developed enough to show that about her transition, but she’s starting to feel good about herself and Emilio notices,” she explains. The goal is simply that we stop seeing her in the simplest terms, in the most convenient definitions. Sincerely, The Breakfast Club.
Pretty Woman (1990)
Every Cinderella story needs a fairy godmother, and for Pretty Woman’s Vivian (Julia Roberts) that magical intervention comes in the form of Edward’s (Richard Gere) credit card and a series of shops on Rodeo Drive. It’s the ultimate fashion revenge fantasy – denied service while dressed in her more provocative clothes, Vivian gets treated like a princess at the hands of Mr. Hollister (Larry Miller) and strolls the streets of Beverly Hills, getting the last laugh with the haughty shopgirls who rejected her. Cinematographer Charles Minsky says the city of Beverly Hills was more than accommodating when it came to shooting this shopping montage on Rodeo Drive, giving them access to storefronts, allowing them to shut down traffic, and even getting permission to shoot inside Gucci and other swanky stores for entire days at a time. Minsky says they used a crane in the middle of the street to get the shot of Roberts diagonally crossing Rodeo that kicks off the sequence.
While it was all about the big stores and locations for Minsky, costume designer Marilyn Vance reveals that none of Vivian’s clothes were from big-name labels but were instead designed entirely by the wardrobe department. “We didn’t think about labels,” she explains. “We thought about what a girl like her would be looking at and be interested in. I got inspiration from magazines. I had to buy those magazines that were fifty bucks that had all the fashion shows. I just thought about what she would think was fun or sophisticated.” Vance says this sequence was all about paring down, helping Vivian find a more elegant look in contrast to her messier, over-the-top “before” look.
The sartorial money shot comes when she walks down the street in a white coat dress paired with an oversized black sun hat and white gloves. Vance designed the dress for Roberts, hand-selecting the real gold buttons that dot the front and the hat and her upswept hair. “That dress was really elegant,” she explains. “The sleeves were a little bit puffed out, but just the fit of it and the length.” Minsky says they used a Steadicam and a transition wipe on a parasol to make that moment a gradual reveal. “She shows up fresh, completely scrubbed like a new person and that was important for [director Garry Marshall] to make that transition cinematically,” he says. “We went out of our way to come up with it.” It required they shut down a portion of Rodeo Drive and block multiple lanes of traffic.
None of the production team had any idea this sequence would feature the titular Roy Orbison song if only because at the time, the film was called 3000 and was a much darker project. But it’s Roberts who truly made the moment indelible — according to Minsky, the actress herself riffed on the iconic “Big Mistake – Big – Huge!” line to land on the final version. We would call that a big stroke of genius (huge!).
Costume designer Mona May began Tai’s grunge-to-glam transformation with Cher cutting Tai’s lavender blouse into a crop top. “Don’t we all try to cut our clothes? That’s trying to find yourself,” May explains. “We had at least 10 shirts. We were having fun with it, trying to cut the sleeves off and make it into a vest.”
David Bowie’s ‘Fashion’ was the temp track here, but music supervisor Karyn Rachtman wanted something fresher. So she hired David Baerwald to write ‘Supermodel” and Jill Sobule (“I Kissed a Girl”) recorded it. “He is one of the rare songwriters that will do research and actually write for the picture,” Rachtman explains. “The research was Sassy Magazine. That’s where he got lyrical ideas about ‘writing school reports about how much she loves her jeans.’ Even though none of them want to be ‘Super Models,’ the idea of the word made sense.” Like, totally.
Miss Congeniality (2000)
To become a believable beauty pageant contestant in Miss Congeniality, Gracie Hart (Sandra Bullock) has to undergo a makeover with militaristic precision – complete with waxing, plucking, and a percussive score meant to evoke a military mission. The results are an epic success, as Gracie exits an airport hangar in a jaw-droppingly short lavender Hervé Leger dress to the tune of “Mustang Sally.”
Costume designer Susie DeSanto says they experimented with several gowns, including sheath-dresses and more flowy silhouettes. “We wanted something that you couldn’t believe it was the same person,” says DeSanto. “We really wanted to show off her figure. Somebody who wears a really tight, short Hervé Leger dress is somebody trying to attract attention. You don’t rock a dress like that if you’re trying to hide who you are.”
While Bullock’s self-confidence and expert physical comedy make the scene land, it’s the “Mustang Sally” track that ties it together. Music supervisor Steve Schnur reveals the track wasn’t licensed but instead recorded specifically for the film. They hired Los Angeles band Los Lobos to put their own spin on it. “We went through the pre-recorded versions of the song. They didn’t work as well,” he explains. “We needed that sexy reveal. It had to have some Hispanic element to it; we were in Texas. We wanted the band to be who they were because we wanted to go back to that old school feel of ‘Cisco Kid,’ that sort of sexiness and all the percussion.” And the cherry on top? Bullock, who worked closely with Schnur on every song selection, was present for the recording session on Sunset and she plays the tambourine on the final version of the track that plays in the film. Now how’s that for a talent portion of the competition?
The Princess Diaries (2001)
“I take ‘This!’ and ‘This!’ and I give you – a princess.” Anne Hathaway’s makeover moment as Princess Mia in The Princess Diaries revealed her true beauty to the world after a hilarious sequence in which Paolo (Larry Miller) enters his makeshift salon with all the swagger of a gunslinger and wrecks havoc on her bushy hair (all of which is really Hathaway’s teased to insane proportions) and Frida Kahlo-esque eyebrows.
Screenwriter Gina Wendkos spent more time rewriting this scene in revisions than any other. “[Garry Marshall] needed a much clearer progression from the ugly duckling to the ingenue,” she says. “He needed the exact things – we give her a form for her eyebrows; we lighten and tame her hair; we sculpt her cheekbones – opportunities for him to then infuse his comedic touches.”
Infuse he did – working with actor Larry Miller to improvise and craft hilarious moments like shrieking at the sight of Mia, breaking her glasses, and eating a cucumber slice resting on her eyes. Marshall devised brilliant shots like Paolo drawing his styling tools from his pockets like pistols. “He gave me the energy and machismo to make that look like Wild Bill Hickock,” explains Miller. “That was the idea.” While Mia’s makeover is serious business, Miller and Wendkos stress the environment on set could not have been more playful and free. “I wrote him to be over-the-top,” muses Wendkos. “But Garry knew how to make Larry explode.”
The Devil Wears Prada (2006)
In order for Andy (Anne Hathaway) to earn respect in her new position as assistant to Miranda Priestley in The Devil Wears Prada, she has to majorly up her fashion game, which is easy when a girl has access to a fashion magazine’s closet of designer duds. Runway magazine’s closet is the stuff sartorial dreams are made of – and that’s about as tangible as it was. “We actually only had like two or three shelving units,” reveals director David Frankel. “We had to shoot the shot several times and move the units and redress them. It was technically painstaking, and it’s probably the fanciest visual effects element in the whole film.” They even upped the wow factor by adding the hint of a choir into the score at the moment Andy enters the closet.
With the assistance of Nigel (Stanley Tucci), Andy raids the closet pulling a bunch of items, including an eye-catching orange poncho that was a personal piece from costume designer Patricia Field’s collection. “It was a present from Helen Yarmak, who is a furrier in New York,” Field says. “That fur piece is back in my closet. I overused it and abused it.”
While some films might opt for a montage sequence of Andy’s many looks, Frankel says they always intended this to be a hard before and after. “We had a bunch of montages built into the storytelling,” he says. “It was fun to see her transformation in an instant. It’s so stunning when she shows up in the Chanel outfit that it doesn’t need a build-up.” There might not be any build-up required, but Frankel used slow-motion to really milk the moment. That costume was an early automatic selection, and Field wanted it to give Andy a touch of smugness. “I wanted to see Chanel interpreted for young people,” Field says. “It’s Chanel as a classic and modern. The boots, the mini-skirt – I treated it a little bit punky.”
It’s a look that certainly impresses Andy’s co-workers Emily (Emily Blunt) and Serena (Gisele Bündchen), wowing them as she enters in slow motion with a little hair flip. Gisele was a last-minute addition to the film, after meeting screenwriter Aline Brosh McKenna on a plane, and Frankel was pleasantly surprised to discover what a good actress the supermodel was, even improvising the scene’s last line, “I think she looks really great.”
Though Andy’s transformation might feel subtle to the audience, Frankel says it dictated the entire production schedule. “We had to plan our schedule around her look, rather than our locations,” he says. “To make her glam and make her un-glam was such a lengthy process, it was easier for the whole movie unit to move to a new location rather than change Annie’s hair and makeup.”
How do you make over a larger-than-life Disney princess who kicks off the movie in a 25-pound ballgown? For Giselle (Amy Adams), Enchanted costume designer Mona May opted to make her under.
The sequence begins with a shopping montage, in which May even cameos as an employee at a perfume counter. Giselle moves to a softer, more contemporary look as first signaled by her coral smock and turquoise towel she wears in the hair salon. May says they never considered having a montage of Giselle trying on different looks. “We always wanted it to be a surprise,” she explains of the purple ballgown’s reveal.
Though May designed the character’s sleek gown herself, she wanted it to feel like something Giselle could buy at Bergdorf’s. “It’s so important to be slick and modern, to be not fairy tale anymore, because we’ve seen the fairy tale. She was the fairy tale princess. She’s now a modern girl. She’s deciding to stay here to really understand this world, to know her feelings and who she is. This silhouette and the color really supported that,” says May. “It wasn’t the dress was wearing her and where is Giselle? It really was Giselle. She’s right here. She’s ready to embrace this new journey.”
May designed the gown with Giselle and Robert’s (Patrick Dempsey) dance in mind, taking inspiration from Ginger Rogers’ gowns from 1930s musicals and from concept drawings of the original Disney princesses locked away in the vault. “You want to have a follow through [on] the Disney princess look, but then make it fresh,” May explains. “She’s one of the first princesses in Disney history to save the prince. That feminine strength had to come through the dress.”
For more Untold Stories from My Best Friend’s Wedding and your other favorite rom-coms, pick up the new double issue of Entertainment Weekly on stands Friday, or buy it here now. Don’t forget to subscribe to EW for more exclusive interviews and photos — and follow #LoveEWstyle on Twitter and Instagram.