Adventures in Babysitting starred Elisabeth Shue as Chris Parker, a girl who just wants to spend a quiet evening babysitting 8-year-old Sara Anderson after her boyfriend, Mike (Bradley Whitford), stands her up on their anniversary. Instead, she finds herself—and the kids in her charge—entangled in an attempted murder plot.
1. PARAMOUNT WAS ONLY INTERESTED IN MAKING THE MOVIE IF IT STARRED MOLLY RINGWALD.
Producers Debra Hill and Lynda Obst brought the project to Paramount first, because the studio had a "first right of refusal." Paramount told them that the movie had no commercial appeal unless Ringwald starred. Walt Disney's Touchstone disagreed.
Though it was Elisabeth Shue who eventually landed the role, she faced some stiff competition. Valerie Bertinelli auditioned for the part, but the casting director felt that she came off as "mean and angry" at the audition.
2. IT WAS CHRIS COLUMBUS' DIRECTORIAL DEBUT.
Chris Columbus (screenwriter of Gremlins and The Goonies) chose Adventures in Babysitting as his directorial debut after reading more than 100 scripts. Columbus believed Babysitting would be a comfortable way to break into directing because it “was on a small enough scale."
He may have been new to the director's chair, but Columbus knew what he wanted. He gave his actors a list of movies to watch, including Martin Scorsese's After Hours (1985) and a Marx Brothers movie. "I think it was Horse Feathers (1932) or Duck Soup (1933) with the Marx Brothers to get some of that screwball comedy timing down, which I think Elisabeth Shue just did a great job at," Keith Coogan (who played Brad Anderson) told CNN in 2011.
3. MOST OF THE MOVIE WAS SHOT IN TORONTO, WHICH WAS TOO CLEAN.
The crew had to spread garbage around the streets so the Canadian city would look like Chicago. They had someone guard the street to prevent Toronto workers from cleaning up the garbage. "Some kind person from the city of Toronto always comes along and clears up the trash," production designer Todd Hallowell groused.
4. THEY BROKE INTO THE CHICAGO SUBWAY TO SHOOT.
When pickup shots were needed for the L train sequence at 3 a.m., no Metro representatives were around to help the crew. The stunt coordinator had to pick the lock to the Metro platform to get their work done.
5. SARA WAS ORIGINALLY INTO HE-MAN AND SHE-RA, NOT THOR.
But those characters "meant nothing" to Columbus. "But I was a huge Marvel comic book fanatic, and so I thought Thor would be an interesting character to go with—not having any idea that 20 years from then, all movies would be based on comic books.”
6. ELISABETH SHUE LOVED HAVING THE "BABYSITTER BLUES."
Shue told The A.V. Club that it was all "a very special experience for me, because it was the first movie I was kind of the star of ... I just remember there was such an innocence to making that movie, and so many things I got to do, like singing the blues. That was probably the best scene I’ve ever gotten to do."
7. POSING FOR THE FAKE PLAYBOY CENTERFOLD WAS THE TOUGHEST THING SHUE HAD EVER DONE.
"Please emphasize I did not take off my clothes for the shoot," Shue told the Los Angeles Times in 1987. She said it "was the toughest thing" she had ever done.
8. SHUE BROKE BRAD'S HEART, BOTH ONSCREEN AND OFF.
Coogan, after acknowledging their over-six-year age difference, brought up the prospect of dating to Shue over dinner. The actor said Shue then "laughed in my face. And that's exactly the laugh she does in the movie. She totally crushed my heart and I took that with me for the movie. When the frat boy rescued her in the movie, I was very jealous and felt very possessive of her."
9. BRADLEY WHITFORD WAS WORRIED ABOUT BEING TYPECAST AS A JERK.
"I was in New York after Adventures In Babysitting—I’d been playing all these jerks—and it was one of the first times anybody recognized me," said Whitford. "A homeless guy said, 'Hey, you’re that guy! You’re in those movies, right?' ... 'Yeah, why do you always play a**holes?' I think I called my agent and said something like, 'Is that a problem? Should I worry about playing an a**hole all the time? Could that damage my career?'" The future The West Wing star was told by his agent that he didn't have a career to damage.