Adventures in Babysitting, Adventures in Babysitting is a 1987 comedy film written by David Simkins, directed by Chris Columbus, and starring Elisabeth Shue, Bradley Whitford, Maia Brewton, Anthony Rapp, Penelope Ann Miller, Keith Coogan, and a brief cameo by blues singer/guitarist Albert Collins. Although it is set in Oak Park, and Chicago, Illinois, with much of the action taking place in the city itself, the movie was filmed primarily in Toronto.
* Elisabeth Shue as Chris Parker, a high school senior whose boyfriend cancels their date, so she goes to babysit the Andersons. She has an upbeat though very mature personality, taking the responsibility thrust upon her being trapped in Chicago with her charges very seriously. She is compassionate and friendly, though naive when it comes to meeting the “right guy.”
* Penelope Ann Miller as Brenda, Chris’ best friend, terrified while in the bus station. A little neurotic, Brenda runs away from home due to unspecified stress and becomes trapped in the bus station downtown, prompting Chris to come pick her up. She is persistent, edgy and positively, blind without her glasses, which are stolen early on.
* Bradley Whitford as Mike Todwell, Chris’ boyfriend who canceled their anniversary date for another girl. He is obnoxious, chauvinistic, and only after a girl who puts out easily. He is regarded as a jerk and once beat Daryl up under suspicion that he touched his Camaro. His license plate is well-known as reading “SO COOL.”
* Maia Brewton as Sara Anderson, an 8-year-old girl who idolizes Thor. She is the youngest and most impressionable, Brad going to lengths to keep her from being exposed to Daryl’s overtly sexual personality. Sara is best known for wearing her Thor helmet and carrying around a plastic hammer. She is fun-loving and caring and attempts to offer her helmet for payment of a car tire when the mechanic has an uncanny likeness to the famed god Thor.
* Keith Coogan as Brad Anderson, a 15-year-old boy who has a crush on Chris. He is obsessed with becoming popular and more worthy in Chris’ eyes. He’s not afraid to speak his mind and often tries to be more mature than Daryl, but in his attempts to act cool he can tend to make some pretty big mistakes. His foot-in-mouth syndrome is solved at one point by having a knife thrown into his toe when trying to intervene in a gang fight.
* Anthony Rapp as Daryl Coopersmith, Brad’s sex-obsessed best friend. Daryl is a sex-crazed, ambitious, and fun-loving party animal, though he has never been to a party nor had sex. He thanks Chris for the best night of his life “so far” and is responsible for stealing a Playboy full of stolen car orders, sending a gang after them all to try and replace the one he stole from his dad to show Brad.
* Calvin Levels as Joe Gipp, a compassionate, streetwise criminal who helps Chris and the others on several occasions. He knocks out his boss as a sign of resignation and is known for telling Chris when seeing a Playboy centerfold who looks like her, “She don’t even compare to you.”
* Vincent D’Onofrio as Dawson/Thor, introduced as a hard-bargaining curmudgeon who is nobody’s friend. After having been given a gift from Sara, who claims him to be her hero, Dawson gives the repaired car back to the group after initially refusing, as Chris was $5 short.
* George Newbern as Dan Lynch, a college student who falls in love with Chris and refuses to believe she is merely a high school student. He finds Sara’s skates in the back of his Jeep after dropping the kids off at Dawson’s garage and returns them, revealing he actually wanted to see Chris again. He becomes her new boyfriend in the end.
* John Ford Noonan as John Pruitt or “Handsome” John Pruitt, a tow truck operator who picks Chris and her friends off the side of the highway and offers to pay for the tire. He is short-tempered, however, and immediately veers to his house to take care of the man with whom his wife is having an affair. He goes on the lamb after the assault charges catch up with him, but he gives them the directions to Dawson’s garage.
* John Davis Chandler as Bleak, the ringleader of a gang of car thieves that Chris and the others encounter. He is smarter, and more suave than Graydon, his counterpart but his ambition to meet his goals often leaves him blind sided.
* Ron Canada as Graydon, Bleak’s second in command. He has a short temper and is nervous when met with confrontation with his boss. He tends to leap before he looks and gets himself into some vary precarious positions.
* Albert Collins as Himself portrayed as a player in a Chicago Blues club, he insists on anyone who comes on his stage to “(not leave) this place without singin’ the Blues”
* Lolita Davidovich as Sue Ann, a lonely girl at a frat party whose dumb jock boyfriend attacks Darryl when she attempts to have sex with him for being compassionate to her needs.Adventures in Babysitting
