Shirley Lyner (Katherine Waterston) is your normal student. She needs to save money for college so in her spare time (when she’s not studying) she runs a babysitting service for extra money. She’s a babysitter for Gail and Michael Beltran (Cynthia Nixon and John Leguizamo). She starts having an affair with Michael and he gives her a big tip to keep her quiet.
After Michael starts paying Shirley for sex and one of his married friends learn about this agreement, it gives her an idea to turn the babysitting service into a something not so wholesome. Shirley gets a calendar filled with “appointments” and starts taking her cut as the pimp. She eventually gets in over her head and as her life begins to fall apart, suddenly saving for college and getting into one isn’t so important.
John Leguizamo is great as a married man who’s going through a mid-life crisis, and Katherine Waterston is great as the ingénue he gets involved with, but the film just doesn’t come together like it should. Writer/director David Ross says the movie is about identity and he specifically wanted to do a movie about prostitution — why people pay for sex, how everyday people try to separate sex from intimacy, and how the attempt to remove sex from intimacy begins to break down.
The Babysitters has a couple of extras on the disc. You get an interesting, informative audio commentary from writer/director David Ross and star Katherine Waterston. Among little tidbits that you learn is that The Babysitters was written as a student project. Throughout the commentary Ross and Waterston go over the story's origins and how the film was shot. The commentary was interesting but it could have benefited by including Leguizamo.
There’s also "Making The Babysitters", which features exclusive interviews with John Leguizamo, Katherine Waterston and David Ross. The stars talk about why they liked the script and why they agreed to do the film, while Ross talks about the origins of the film and how it developed; the idea was much better than the finished product.
The Babysitters is an interesting look at sex and what happens when you try to separate sex from intimacy but unfortunately it falls short in the execution.