If she applied, "The Baby-sitters Club" would probably reject Katherine Waterston. Although the Connecticut-raised actress experienced the typical teenage ups and downs, her travels through Europe and a preference for Anne Sexton's poetry ultimately suggest a precocious interior world. The enigmatic quality that belies Waterston's angelic face is exactly what makes her so fascinating as Shirley, a high school Heidi Fleiss, in The Babysitters. Waterston admits only to being in her early twenties -- barely legal, but not jailbait. "I still get carded for cigarettes and told not to sit in emergency exit rows," she laughs.
In The Babysitters, Shirley both unwittingly and obsessive-compulsively launches an underage prostitution ring from her bedroom computer after an unexpected (and afterwards compensated) make-out session with neighborhood dad-crush Michael (John Leguizamo). The film, which premiered at the Toronto Film Festival, hits theaters this month. "These girls represent a nostalgia for the men's lost youth," explains Waterston. "People are complicated and capable of anything." To that point, Waterston even braved her first topless scene. "When I saw it, I was shocked. But it's crazy not to expect regular humiliation as an actress."
The talented progeny of former model Lynn Woodruff and actor Sam Waterston (Law & Order) was curiously inspired by her father's career: "I've always been jealous of his work with Woody Allen [in Crimes and Misdemeanors]. It's like, âYou lucky bastard!'" She also covets one of his former co-stars. "I'm jealous he got to kiss Charlotte Rampling. I'm impressed by women who embrace the aging process," notes the baby-faced actress. Like Rampling, Waterston seems to have the ingenue-with-a-dark-side role down pat. Next up, she'll play an invalid held prisoner by a psychotic killer in 2009's The Factory, alongside John Cusack. "I'm just starting to notice patterns in my career," she says. "I figured I'd get typecast as the girl in the corset weeping in a field, but I keep getting these edgier parts."
Photographed in the VIP room at Marquee * Styling by Quinn Asteak * Hair and makeup by Angela Di Carlo * Katherine wears a dress by Lyn Devon and belt by Preen.