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The 7 Best Molly Ringwald Roles

February 18, 2013  |  10:07am
The 7 Best Molly Ringwald Roles

Today, we celebrate Molly Ringwald’s 45th birthday, and while she’s blowing out significantly more than 16 candles this year, she’ll always be our Teen Queen, a mirror for generations of adolescent girls to hold themselves up to.

Above all, what makes Ringwald the ultimate high-school star is her versatility; she’s just as believable as the most popular girl in school—spoiled rotten and misunderstood—as she is as a quirky New Wave aficionado from the wrong side of the tracks, or an angsty, anonymous face in the crowd just trying not to feel invisible. Name a teenage stereotype and Molly Ringwald’s played it convincingly while simultaneously turning it on its head—and that’s why we can all relate. After all, isn’t searching for an identity and fighting against others’ perceptions of you what being a teenager is all about?

So, while we may not have a cake to share atop a dining room table with her, we haven’t completely forgotten either. We’re here to wish Molly Ringwald a happy birthday by counting down her seven best roles.

7. Fresh Horses (1988)
Ringwald reunites with her Pretty in Pink costar Andrew McCarthy here for one of her more adult roles—and the chemistry between the two is evident. She stars as Jewel, a 16-year-old from Kentucky (who claims to be 20) with an abusive husband, who falls in love with Matt (McCarthy) after meeting him at a party. It’s sort of a darker, bizarro version of the pair’s first movie together, and Ringwald manages to outshine the rest of the cast, which includes Viggo Mortensen and Ben Stiller.

6. The Pick-Up Artist (1987)
By 1987, Molly Ringwald had already spent a good chunk of her career rolling her eyes and rebuking the advances of guys—be they the impossibly charming (Duckie in Pretty in Pink), the well-intentioned-but-a-little-gross (Farmer Ted in Sixteen Candles) or the downright smarmy (Steff in Pretty in Pink). So when she was pitted against Robert Downey Jr.’s smooth-talking ladies’ man Jack Jericho in The Pick-Up Artist, she found herself right in her wheelhouse as Randy, the uptight museum guide he tries to woo.

5. For Keeps (1988)
For Keeps is another one of Ringwald’s more “grown-up” roles (she plays a high-schooler who gets pregnant and experiences postpartum depression after having the baby), but what keeps it from being just another after-school special is the air of immaturity she brings to the role. Her character Darcy juggles marriage, school and a family all before her 18th birthday, and Ringwald’s innocent portrayal of the small details (like when she calls her boyfriend’s penis “cute” in the clip below) clues us into the fact that she’s not really ready for any of it.

4. The Facts of Life (1979-1980)
One of Ringwald’s earliest roles was the chipper Molly Parker on The Facts of Life. She was young—just 11 when she started—but she was charismatic enough to steal the limited number of scenes she appeared in as a supporting character. She may not have been the “Joan Baez of the ‘80s” as she predicted in the clip below, but she certainly went on to rule the decade.

3. Sixteen Candles (1984)
It’s the movie that made Molly Ringwald a star, and rightfully so: as Samantha, the everywoman whose parents forgot her birthday and whose crush doesn’t know she exists, she appeals to the angsty high-schooler yearning to be seen in all of us. Samantha’s undeniably middle-of-the-road—she’s not popular, but she’s not a geek; her home life is messy, but it’s not dysfunctional—and that gives her mass appeal, so much so that her story’s become sort of a modern fairy tale, the American Dream of teen romantic comedies.

2. The Breakfast Club (1985)
We shouldn’t have to tell you what makes The Breakfast Club an all-time classic. There’s not a single weak link in the film’s ensemble cast, and Ringwald holds her own as Claire, the princess forced to spend her Saturday in detention with a brain, a basket case, a jock and a criminal. She gives a richly layered performance, turning what could easily be a one-dimensional character into someone we pity, empathize with and root for—which, if you haven’t seen the movie, is kind of the whole point.

1. Pretty in Pink (1986)
Let’s ignore the fact that she ends up with the wrong guy in the end (Team Duckie for life!) and examine what makes Pretty in Pink’s Andie so impossibly cool: She works in a record store and has killer taste in music. Her outfits are daring and incredible. She brushes off insults from evil richie-rich Steff (James Spader) like they ain’t no thang. She supports her deadbeat dad and essentially serves as head of their household. But most importantly, she’s the picture of courage, staying true to herself the whole way through and never changing to please Blane and his wealthy friends—and if there’s any single movie character teen girls should be modeling themselves after as they attempt to swim the treacherous waters of high school without drowning, she’s the one.

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