A highlight of the parody Not Another Teen Movie is when two guys make a bet on how they can make “the ugliest girl in school” the most popular. They look around, skipping the conjoined twins, the albino, the hunchback and someone who looks like the Wicked Witch of the West to settle on… Chyler Leigh, who’s wearing glasses and frumpy clothing and yet somehow that makes her the least attractive person around. It’s an obvious shot on how the movie She’s All That presented Rachael Leigh Cook as some sort of leper. It works because it hits how Hollywood has long had a very different definition of “plain” or even “ugly” than the rest of the world.
It’s been that way for years, slews of adaptations of works that decide to cast a character described as not that attractive with a gorgeous actress and try to sell it as logical. Some movies have fun with it; the plot of Shallow Hal is Jack Black hypnotized into seeing his obese girlfriend as Gwyneth Paltrow while The Other Guys has Will Ferrell not seeming to grasp his “battleaxe” wife is played by Eva Mendes. It plays into movies of a character looking frumpy before a big makeover (Anne Hathaway in The Princess Diaries). Now and then, they do try to ugly her up with makeup and sometimes succeed (Tilda Swinton in Snowpiercer) but a lot of the time, you keep hearing them described as unattractive when it’s simply not the case. Here are 10 most notable cases of this odd phenomenon, 10 roles of ugly or at least unattractive characters played by the most gorgeous ladies imaginable and how laughable it is to have filmmakers think we'll buy it.
10 Emma Stone - The Help
In the book, the character of Skeeter is made out to be a plain woman who has trouble finding men and throws herself into her writing career which leads to helping out the black maids. That’s made a point of the film version as well, talk of how Skeeter can’t find a man as she’s not attractive enough. However, the casting of Emma Stone hurts that entire idea as giving the gorgeous woman frizzled hair does nothing to defeat her attractiveness and actually far hotter than any of the other women in the cast, making her struggle to be accepted rather baffling to watch taken seriously.
9 Zooey Deschanel - Failure To Launch
Before his current reign as Oscar-winning serious actor, Matthew McConaughey was stuck in seemingly endless rom-coms. Among them is this 2006 film where he plays a guy still living with his parents so they hire Sarah Jessica Parker to fake-romance him and get him out of the house. Far more interesting is the subplot as McConaughey’s friend, Ace (Justin Bartha) is described as downright ugly by everyone despite the fact he quite clearly is not. When Ace finds out the truth, he blackmails Parker into a date with her roommate, Kit, played by Zooey Deschanel and it’s made out to be a huge shock due to how horribly unattractive Kit is. Indeed, many characters note the two seem perfect for one another because they’re both so ugly no one else would want them. To call the lovely and funny Deschanel ugly and unable to get a date is totally ludicrous (just as much as Bartha) and a bigger joke than anything else in the film although she does make it more bearable than either of its main stars.
8 Mae Whitman - The Duff
From the start, this movie asks you to buy the idea of Mae Whitman being the “Designated Ugly Fat Friend” of her high school clique. The woman is not ugly or fat by any means and they try to get around it by her friends claiming it’s just because she’s so socially awkward and not as attractive. However, her awkwardness is adorable thanks to Whitman’s cute looks and good humor and thus more endearing than driving guys away. In many ways, she’s far hotter than her “hot” friends (even Skyler Samuels) and thus defeating the entire concept which may explain the movie being a failure despite Whitman’s great charms.
7 The Character Of Medusa
In Greek mythology, this beautiful woman slept with Poseidon (how consensual it was varies on the version) and was cursed by Athena into a monster so hideous that one look could turn anyone into stone. In the original Clash of the Titans, Ray Harryhausen showed her as a half-snake creature who was truly horrifying. However, most versions go for the idea of her being still quite beautiful, simply snakes for hair and somehow that’s still enough to turn someone into stone. A key example is Percy Jackson and the Lightning Thief as the screenplay imagined Medusa as green-skinned and spitting venom. But for the final film, you had Uma Thurman in glasses and a turban over her hair yet still being sold as this monster. Likewise, the remake of Clash had Medusa as a half-snake but looking like model Natalia Vodianova - an absolute stunner; although, to their credit, she did show a more horrible look when she petrified someone. It just seems off that a character meant to kill with a look should constantly be shown so lovely.
6 Christina Ricci - Penelope
This quirky 2006 comedy has Christina Ricci as a woman cursed to be born with the features of a pig until she can be accepted which her rich parents think means she gets married to a wealthy guy. Much is made of her being so hideous that would-be suitors throw themselves out the first floor window upon meeting her, so much that her mother installs shatter-proof glass. However, the “curse” is shown to simply be a pig’s nose and ears which on Ricci look cute and even downright adorable. Trying to sell this “curse” with an actress who makes it work so wonderfully undermines the film and shows how Ricci can make any appearance look quite amazingly hot.
5 Audrey Hepburn - Sabrina
This classic comedy focuses on a young woman treated as an afterthought until a Paris trip gives her a makeover to be glamorous and win the hearts of Humphrey Bogart and William Holden. At the start, Sabrina is told she’s unattractive with a ponytail that “makes you look like a horse.” So who was chosen to play this incredibly plain woman? Audrey Hepburn, easily the most beautiful woman on the planet in 1954. Trying to accept Hepburn as so lonely and homely that she considers suicide is laughable and while that works for her makeover, even the pre-Paris Sabrina is an absolute knockout. Hepburn’s wonderful skill and charm help the movie out but having to accept her pre-“transformation” is a bit much.
4 Amanda Seyfried - Jennifer’s Body
So Megan Fox as a hot cheerleader? Okay, perfect casting. Her character friends with the school loser geek? Strange but might be clever. Said loser geek being played by Amanda Seyfried? That’s where it falls apart. The woman is arguably sexier than Fox in many respects and having her dressed down in frumpy clothing and glasses does nothing to hide it. It also works against the plot as a key part is Seyfried’s character blossoming into a beauty but she’s already gorgeous. On the audio commentary, even the filmmakers acknowledge trying to sell Seyfried as “the ugly one” never worked and while hot to watch, doesn’t make much sense as a film.
3 The Character Of Jane Eyre
The term “plain Jane” comes from Charlotte Bronte’s classic novel of a repressed woman yearning for romance and adventure and considered a gothic groundbreaker. The character being so plain is the key to it all and why she endears to readers. However, just about every film adaptation (not just Hollywood but England as well) seems to ignore that in the casting. Among those who have played Jane are Virginia Bruce, Joan Fontaine, Susanna York, Charlotte Gainsbourg and, most recently, Mia Wasikowska. Not a single one of them can possibly be called “plain” and in fact, far more attractive than their co-stars who are supposed to be the beautiful ones. Remarkable how so many takes on the classic miss the key part of the character despite the talents of those involved.
2 Kate Winslet - Little Children
It’s one of the best performances of Winslet’s long and acclaimed career but also a rather baffling one. She plays a woman pulled into an affair with another man in a dark take on suburban life and it’s discussed how unattractive her character is and even told “beauty is overrated.” Which might work if she wasn’t been played by Kate Winslet who goes all out in nude scenes that disprove the idea of her being unattractive majorly and while the movie is good, trying to sell Winslet as a frumpy gal is a losing proposition.
1 Charlize Theron - Monster
This is an interesting case as you can certainly agree that Aileen Wuornos was hardly a beauty. Executed for several murders, the woman was very unattractive and thus the casting of Charlize Theron in the role raised eyebrows. However, Theron blew away doubters by gaining 40 pounds, shaving her eyebrows and undergoing a makeup job that made her nearly unrecognizable to play the role. It won her massive critical acclaim and the Oscar and it’s a sensational performance to watch. However, the fact remains it’s still one of the most incredibly sexy women alive in the role and no matter the makeup or her weight, that innate aura of hotness can’t be beaten, no matter what. Which makes it all the more impressive that she could pull off this incredible part so well.