After her boyfriend, Mike Todwell (Bradley Whitford), cancels their anniversary date, 17-year-old Chris Parker (Elisabeth Shue) volunteers to babysit for the Andersons' children, 15-year-old Brad (Keith Coogan) and 8-year-old Sara (Maia Brewton). However, she gets a frantic phone call from her friend, Brenda (Penelope Ann Miller), who has run away from home, asking her to come pick her up after running out of money from the cab ride to the bus station. She takes Brad, Sara, and Brad's friend, 15-year-old Daryl Coopersmith (Anthony Rapp), and sets out, but they get a flat tire, find the spare compartment empty, and become stranded on the highway.
A friendly tow truck driver, "Handsome" John Pruitt (John Ford Noonan), offers to replace the tire for free. En route to the garage, he gets a call on his CB saying that his wife is cheating on him and he heads home. A brief shootout ensues and during their scramble to get away, the kids unwittingly climb into a Cadillac just as it is being hot-wired by a professional car thief, Joe Gipp (Calvin Levels). Gipp promises to help them get on their way home but not before bringing them to a chop shop, where they are briefly detained. Daryl finds a Playboy magazine and steals it before they escape onto the building's roof; however, it contains incriminating notes and the car thieves follow them. They stumble into a Blues club and are forced to sing about their ordeal by Albert Collins, receiving applause from the audience. Billy Branch plays himself as the harmonica player in this scene. After they have left, the car thieves are held up when they are forced to do the same thing.
The car thieves manage to once again catch up to the kids, but the four narrowly escape by stowing away aboard a Chicago 'L' train. Inside the near-empty train, Chris and the children become suddenly caught in the middle of a gang fight in which Brad is injured and taken to the hospital (Mercy Medical Center). They again encounter Pruitt, who is on the run due to his earlier fight. He tells them that his boss, Dawson (Vincent D'Onofrio), fixed their car, but he will force them to pay $50 for the tire. They then come across a college fraternity party at which Chris meets a new love interest, Dan Lynch (George Newbern), who manages to gather $45 for them. Daryl almost gets into a fight with a jock whose lonely girlfriend attempts to make out with him. Dan then drives them to Dawson's garage.
In the garage, Dawson appears, and Sara believes he is the superhero Thor. He refuses to release their car due to the $5 shortage, but she pleads with him and gives him her plastic helmet, causing him to change his mind, and he allows them to take the car. On their way through the city, they pass by the restaurant to where Mike was going to bring Chris on their date, and Daryl spots his car parked out front. She goes in to find him flirting with the sleazy Sesame Plexer. Brad and Daryl stand up to him when he insults her. Meanwhile, Sara wanders off and is spotted by Graydon, one of the car thieves. She is chased to the Crain Communications Building where her parents are attending a party. She goes to the renovated top floor and uses a rope to slip out the window. He discovers her and attempts to climb outside with her as she dangles precariously. Chris, Daryl, and Brad go on to the top floor after seeing her out the window and rescue her.
They successfully pick up Brenda and get home, and Chris sends the kids upstairs while she quickly tidies up the mess left earlier in the day. She settles in just as Mr. and Mrs. Anderson come home. She goes up to say good night to the kids and they all thank each other for the greatest night of their lives. As she leaves, Dan shows up to return Sara's skate which she had accidentally left behind in his Jeep, but notes that wasn't the only reason in hoping he could have her a babysitter, to which she says "Maybe retirement can wait." With some encouragement from Sara, and Chris and Dan share a kiss.
A post-credits scene shows Graydon still leaning against the side of the building, desperately waiting for rescue.
- Elisabeth Shue as Chris Parker
- Keith Coogan as Brad Anderson
- Maia Brewton as Sara Anderson
- Anthony Rapp as Daryl Coopersmith
- Penelope Ann Miller as Brenda
- Bradley Whitford as Mike Todwell
- Calvin Levels as Joe Gipp
- Vincent D'Onofrio as Dawson
- George Newbern as Dan Lynch, a college student
- John Ford Noonan as "Handsome" John Pruitt
- John Davis Chandler as Bleak
- Ron Canada as Graydon, Bleak's second in command
- Albert Collins as himself; a player in a Chicago Blues club
- Lolita Davidovich as Sue Ann
- Clark Johnson as Black Gang Leader
- Kirsten Kieferle as Sesame Plexer
This was the first PG-13-rated film released by a Disney film division and was released as A Night on the Town in the United Kingdom. This scene was added to stretch out the bus station segments. It was not in the original script.
Bradley Whitford, who played Mike Todwell in the film, was actually 27 years old at the time of shooting in 1987. He was uncomfortable with the age difference, but Columbus put him at ease by allowing him to use his own Camaro in the movie. The car is later seen with Whitford's actual license plate "SO COOL."
Valerie Bertinelli was one of the actresses who auditioned for the role of Chris Parker.
Box office and reception
The film was a box office success, earning more than $34 million on its $7 million budget. It has received positive reviews, and it currently earns a "fresh" 76% approval rating on Rotten Tomatoes based on 24 reviews.
The film was adapted into an American television pilot of the same name for CBS in 1989. It starred Jennifer Guthrie (who would later co-star on Parker Lewis Can't Lose with Maia Brewton) as Chris, Joey Lawrence as Brad, Courtney Peldon as Sara, Brian Austin Green as Daryl, and Ariana Mohit as Brenda. It was not picked up to a series.
A remake was reportedly planned for release in 2012. Disney Channel star Raven-Symoné was going to star in it, currently titled Further Adventures in Babysitting, but decided to withdraw due to other projects. Miley Cyrus, who was rumored to be attached to the project, has also denied involvement. According to Variety, Tiffany Paulsen was writing the script.
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