In order to sound like as little of a creep as possible, let me put into context how I thought of making this list. When I was in my young teens (mostly between the ages of 14-17) I had several encounters with men who would somehow make a Lolita inference during our conversation. I always thought this was equal parts disturbing and flattering. It was sometimes nice to know that my crushes on inappropriately older gentlemen weren't always entirely one-sided. For any gal who has every been "Hot for Teacher" or longed for a pair of heart-shaped sunglasses, this list is for you.
So to start off the list, I give you the girl who started it all...
Dolores 'Lolita' Haze (Sue Lyon) in Lolita, 1962
I've never seen the remake with Dominique Swain in the title role, but I'm still going to say that this is my preferred version. I love Sue Lyon's portrayal of the flirtatious fourteen-year-old - especially in those moments where she's allowed to be a little bit darker than what the censors would normally allow and explore more of the depth to this character. Plastic heart-shaped sunglasses have become a little bit less childish since this movie's release. Fun fact: Though she was the star of the film, Sue wasn't allowed into the premiere of Lolita because she was a few months shy of her sixteenth birthday (16 being the minimum age required to enter the screening).
Mathilda Lando (Natalie Portman) in Léon: The Professional, 1994
In the film, Portman plays the twelve-year-old neighbor of a hitman in Little Italy named Léon. After her family is murdered, including her four-year-old brother (the only one in the family she actually loved, she says), Mathilda begs Léon to teach her his skills so that she can avenge her family's murders. Natalie Portman looked badass in her big black boots, choker necklaces, striped tee shirts, and her sleek bob that could put Mia Wallace to shame.
Iris 'Easy' Steensma (Jodie Foster) in Taxi Driver, 1976
Never before this movie did I ever say "Gee, I wish I were a twelve-year-old prostitute." As Iris, a New York 'lady of the streets', Jodie Foster got to wear some of the most killer seventies clothing. I'd die for the dusty pink hot pants and red suede wedges she wears when she meets Travis Bickle (Robert de Niro). Though she's onscreen for only a fraction of the movie, Foster's role as Iris and her relationship with Bickle drives the second half of the narrative.
Tracy (Mariel Hemingway) in Manhattan, 1979
As Tracy, the seventeen-year-old love of Woody Allen's philandering 42-year-old Isaac Davis, Mariel Hemingway earned an Academy Award nomination for Best Supporting Actress. And with good reason. Giving the most soft, subtle performance in a film of neurotic characters, Hemingway's Tracy comes off as the most intelligent and mature of the whole lot. She also gets to utter one of the famous last lines, "Not everyone gets corrupted ... you have to have a little faith in people."
Violet (Brooke Shields) in Pretty Baby, 1978
Perhaps the jailbait actress of the century, practically anything from her early career could have made this list (The Blue Lagoon, Endless Love, her Calvin Klein ads), but here is Brooke in her first major (and most jailbait-iest) film role. The film is set in 1917 New Orleans during the last months of legal prostitution. Brooke plays Violet, the twelve-year-old daughter of a prostitute (Susan Sarandon being gorgeous, as per usual), whose virginity is auctioned off by her mother's madame. A photographer by the name of Ernest J. Bellocq is fascinated by Violet's beauty and youth, and marries the girl. Although Brooke is undoubtedly gorgeous, there is still something I find so unsettling about seeing such a young girl painted with makeup and made to be so overtly sexualized ... especially when you consider that this was partially a true story.
Charlotte Goodall (Sue Lyon) in The Night of the Iguana, 1964
Sue Lyon really made a career out of playing over-sexualized teenage girls. Here our little Lolita travels to Puerto Vallarta to pursue the affections of Richard Burton, but she faces some stiff competition from Deborah Kerr and Ava Gardner. Fun fact: Although director John Huston did not have a problem with the international ruckus that Burton and his lover Elizabeth Taylor were causing on the Puerto Vallarta set, Huston banned Sue Lyon's fiance from the set after interfering with film production too many times.
Angela Hayes (Mena Suvari) in American Beauty, 1999
Mena Suvari kind of ruined the entire idea of red rose petals for me, but it was still a stellar film.
Ivy (Drew Barrymore) in Poison Ivy, 1992
After befriending schoolmate Sylvie Cooper, Ivy - a seductive scholarship student at an exclusive Beverly Hills prep school - makes designs on Sylvie's father. Ivy is a calculating young girl who was ready and willing to do anything to get something she wanted. Drew Barrymore's fifteen-year-old femme fatale is far and away the most dangerous girl on this list.
Baby Doll Meighan (Carroll Baker) in Baby Doll, 1956
In this Elia Kazan picture, Baker plays "Baby Doll," the sweetly uneducated teenage bride of Karl Malden. In order to compound this fact, Baker sucks her thumb a lot. The film was widely condemned upon its release, with Time Magazine saying in its review at the time that it was the "dirtiest American-made motion picture that had ever been legally exhibited." The Legion of Decency even succeeded in getting the film withdrawn from theatres because of it's "immoral content." Fun fact: Despite being thirty-years-old at the time, Marilyn Monroe was chosen by Tennessee Williams personally to star in the film. Monroe, who wanted the role badly, was finishing up her year-long exile from Hollywood to improve her acting talent and almost got the role. Kazan ultimately went with film newcomer Carroll Baker, who had worked together at the Actor's Studio.
Jenny Mellor (Carey Mulligan) in An Education, 2009
In 1961 England, sixteen-year-old schoolgirl Jenny is swept up in a romance with the charming and sophisticated David, who is over twice her age. With Mulligan racking up the awards this past year, it goes without saying that her portrayal of the young, impressionable schoolgirl was a hit among critics and audiences alike. The film is set in the same year as Kubrick was filming his version of Lolita, so I think that completes a beautiful circle there, doesn't it?
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