Adventures in Babysitting (1987)
Chris Parker agrees to babysit after her "dream" date stands her up. Expecting a dull evening, Chris settles down with three kids for a night of TV... and boredom. But when her frantic friend Brenda calls and pleads to be rescued from the bus station in downtown Chicago, the evening soon explodes into an endless whirl of hair-raising adventures! Babysitter and kids leave their safe suburban surroundings and head for the heart of the big city, never imagining how terrifyingly funny their expedition will become!
In the suburbs of Chicago, the seventeen year-old Chris Parker is in love with her boyfriend Mike. When Mike stands her up and cancels their dinner in Chicago, Chris accepts to babysit the siblings Sara and Brad. But her friend Brenda calls her telling that she decided to run away home but now she has repented; she begs Chris to rescue her from the bus station in downtown Chicago. Chris makes a deal with Sara and Brad and when she is ready to drive to downtown, Brad's friend Daryl overhears the negotiation and blackmails Chris to go with them. However, when they are on the expressway, Chris has a flat tire and she realizes that she has forgotten her purse in the house. The mechanic Pruitt stops this tow truck and offers to truck the car to his garage. Chris sees no other option and accepts the offer in the beginning of an unforgettable night of adventures in Chicago.
Chris Parker is a popular high school senior living in Oak Park in suburban Chicago. When her boyfriend Mike Todwell, with who she is in love, cancels what was supposed to be a romantic anniversary dinner date at the last minute due to a family emergency, Chris, instead, reluctantly accepts a job to babysit eight year old Sara Anderson, who idolizes Thor and roller skates whenever she can. Sara's high school freshman brother, Brad Anderson, secretly fantasizes about Chris being his girlfriend, the two who only cordially say "hi" to each other in the school hallways, if that, when they run into each other. Chris' babysitting job takes a turn when her naive best friend Brenda, who was planning on running away, frantically telephones from the downtown Chicago bus station realizing the scariness of the situation, she needing a ride home as she has no money. As Chris has no money either to pay for a cab for Brenda, Chris, with Sara, Brad, and Brad's best friend Darryl Coopersmith in tow, drives into the city in Chris' mother's station wagon to pick up Brenda. While Brenda faces her own issues in waiting for Chris, Chris and her charges get into one misadventure after another having to do with, among other things, mechanical problems with the station wagon, a jealous husband with a philandering wife, a car theft ring, a blues club with an unofficial yet unbreakable policy, a gang war, a frat party, a cheating boyfriend, and an office party in an upper floor of a skyscraper. What happens is affected by Chris' need to mind all three kids who want to go off on divergent directions, and the current issue of Playboy whose centerfold has an uncanny resemblance to a certain babysitter. The primary question becomes if Chris can get Sara, Brad, Darryl and Brenda home in one piece before the Andersons get home and discover their adventurous night.
Chris has a big night out planned when her boyfriend cancels on her. She agrees to babysit for a preteen girl and a pubescent boy. She's settled in for a dull night when a girlfriend calls her to say she's marooned at a downtown bus station with very seedy characters around. The three plus one of the boy's friends get into the parents' station wagon for a trip to the inner city. All is well until the flat tire.
Chris Parker is a high school senior that her date stands her up. The only thing she can do now is babysit Brad and Sara Anderson, and their annoying sex fiend neighbor Darryl. When her friend Brenda is trapped in a bus station, Chris has to travel out of the suburbs to the big city. While there and with a flat tire, Chris, Brad, Sara, and Darryl get caught in the middle of a mafia deal lead by Dan Lynch because of a Playboy magazine. Will they be able to get back to the 'burbs?
A babysitter must battle her way through the big city after being stranded there with the kids she's looking after.
- Chris Parker is awaiting the arrival of her boyfriend, Mike Toddwell, to pick her up for a date. When he arrives, he devastates her by canceling their plans to go to a French restaurant in downtown Chicago due to his sister becoming ill. Brokenhearted, Chris has her best friend Brenda come over, and while she is there, the Andersons call asking if Chris can babysit their daughter Sara. Seeing no other plans for the evening, Chris agrees.
When she arrives, she discovers eight-year-old Sara and her fifteen-year-old brother Brad in an argument. Sara had taken Brad's Clearasil and used it to paint another picture of her Marvel hero Thor, prompting Brad to call him a homo and upset her. She manages to blackmail him by telling him in front of Chris (without his knowing) that she would tell Chris about all of his love poems to her. Embarrassed, Brad admits defeat and apologizes to Sara.
After the Andersons leave for the evening, Brad is visited by his best friend Daryl, whose house he was supposed to be staying over that night, but Brad cancels and returns to the living room where he shuts the blinds out from the "stray dog" as he describes him to Chris. Chris gets a call from a frantic Brenda, who had successfully run away from home, but unsuccessfully stranded herself at the bus station downtown. Without the money to pay for a cab ride, Brenda's fear prompts Chris to decide to drive into town. Sara and Brad won't let her leave them home alone, and Daryl's eavesdropping forces her to take him along as well.
In the car, Chris tells Sara a scary story about a man with a hook who kills a babysitter and her children, and when a car tire blowout stands them on the expressway without a spare, she realizes that she forgot her purse at the Anderson's. A tow truck pulls over and "Handsome" John Pruitt offers them a hand, or a hook to the surprise and fear of the children. Offering to pay for the tire repair, Pruitt is distracted by a call and he diverts to his home where his wife is cheating on him. In a resulting shootout, Chris and the others get out of the truck and into a Cadillac, which is being stolen. The thief, Joe Gipp, promises to take them to safety after he drops off the car at a chop shop. However, leaders Greydon and Bleak detain them up in the office for a meeting they were involved in. Daryl boosts a Playboy magazine to replace his dad's, which had been thrown out of the car window earlier by Brad. They then make a tense escape crossing the girders in the warehouse ceiling, escaping outside. The thieves find the Playboy missing, and as it contains incriminating evidence that can be used against them, they give chase.
The kids are chased into a blues club where they are not allowed off the stage until they reveal their predicament in song, much to the cheers and applause from the audience. When they are allowed to leave, they are reminded of their mission and predicament when Darryl attempts to pick up a prostitute on the street who turns out to be a seventeen yo runaway.
Meanwhile Brenda is not having a very good time at the bus station. Having her glasses stolen while resting leaves her practically blind, she mistakes a sewer rat for a kitten, and is laughed at by pest exterminators when she attempts to defend it. A hot dog vendor will not accept her small check as payment, stating "You slip me the cash, and I'll slip you the wiener." But when she says, "I don't have any cash!" he proclaims, "Then I don't have a wiener!"
Another chase from the thieves prompts them to board a monorail where a pair of rival gang members move in to kill each other. Chris intervenes to hold off the fight until they exit the train, and Brad stands up when she is insulted. Brad gets a knife thrown into his shoe, and Chris wields it against the gang, quoting her famous line: "Don't fuck with the babysitter." When they back off, the four of them leave the train and rush Brad to the hospital. After a scare where they think Brad has died, they run into Pruitt again, who tells them that they will need to pay $50 for the tire, as he had to pay for the windshield damage from the gunfight earlier.
They arrive shortly after at a fraternity party. Chris meets a new love interest in Dan Lynch who manages to get together $45 toward the car's tire payment. Darryl gets into trouble with a jock whose lonely girlfriend attempts to have sex with him, and Dan takes them to Dawson's garage. Leaving, and expected never to be seen again as he did not give Chris an address to get hold of him to pay him back, upon entering the garage, they meet Dawson, whose long blond hair and physically fit appearance causes Sara to think he is the alter ego of Thor. Dawson, offended by the $5 shortage, refuses to relinquish the car, but Sara's selflessness in giving him her plastic Thor helmet prompts him to have a change in heart, he gives the car and her helmet to the kids, and lets them go.
En route to the bus station, Chris spots the restaurant that Mike was supposed to take her to that night, and Darryl points out Mike's car in the parking lot. They go in to find that Mike is dating and flirting with the sleazy Sesame Plexer, and it is revealed that Mike was only dating Chris in interest of having sex with her. Brad stands up for Chris, but won't sink to his level. Darryl admits, "I will", and kicks Mike into a dessert cart.
Meanwhile, Sara has slipped out of the restaurant to visit a toy store she had seen, and is approached by Bleak, who spots the Playboy in her backpack. They chase her down to the building that her parents are having their party in, and find through chocolate finger smudges on the elevator buttons which floors to check. Graydon exits in the renovated top floor of the building, and discovers Sara climbing out the window on a rope. Chris, Darryl, and Brad hot on their trail choose the wrong floor and accidentally crash the Anderson's office party. After a brief encounter with Bleak, both he and Chris notice Sara walking along the window ledge outside, and Chris causes Bleak to trip while she and Brad and Darryl go upstairs and discover Sara outside the window. After pulling her up to safety, Joe arrives and explains they were after the Playboy the whole time. They decide to leave Graydon outside and let him "sweat a little" while Joe shows his resignation from the car thieves by punching out Bleak, and they depart the building.
Brenda discovers her glasses and steals them back, only to be chased from the bus station by everyone she had come across. Being chased by the homeless, she runs into the exterminators, past the hot dog vendor, and past the phone booth, which is a homeless man's house. After she gets outside, she is picked up by Chris and the others and she proclaims "What took you guys so long?!"
On the way home, the kids pass the Andersons on their way home. Chris sends the kids upstairs and Brenda home before cleaning up the messes that had been made earlier in the day, coming to settle down just as the Andersons appear in the doorway, not suspecting a thing. Chris goes upstairs to say good night and announces her plans to retire from babysitting. They each admit to each other and thank themselves for "What was probably the greatest night of their lives... so far".
As Chris leaves, Dan makes a surprising appearance to return Sara's skate, which she'd left in his jeep, as well as admit to Chris that he is interested in her. Sara shouts "Kiss him!" from the bedroom window, and they comply happily. Brad, who had come to realize that while they aren't boyfriend/girlfriend, he and Chris can still have a good friendship, accepts that Dan is better for her than he is. He closes the blinds to give the two some privacy, and the credits roll.