[[quoteright:255:http://static.tvtropes.org/pmwiki/pub/images/babysitting_adventures.jpg]]

It was just a simple babysitting job, GoneHorriblyWrong.

Chris Parker's boyfriend can't make it to their date that night, so with nothing else to do, she babysits the Anderson's children Sara and Brad.

Then Chris' friend, Brenda, calls in a panic about running away from home but then changing her mind and asking Chris to pick her up. Chris can't leave her charges behind, so she takes them and Brad's friend Daryl along with her. She gets a flat on the highway, then realizes she forgot her purse. Things just get more crazy from there.

Creator/ChrisColumbus' directing debut, this film was the first PG-13 film released by Disney (albeit under the TouchstonePictures studio name, to avoid the association with strictly family content).
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!!This Film Provides Examples Of:
* AvoidTheDreadedGRating: A MacGuffin being a ''{{Playboy}}'', where Chris is the spitting image of the centerfold, some borderline offensive jokes and a WildTeenParty would be enough, but a couple quick exchanges of the F word were enough to get that PG-13. Though they did have to cut out another scene to keep the rating (see below).
* BadassLongcoat: Chris rocks one throughout the whole movie.
* BastardBoyfriend: Mike. Not abusive, but cold and unfaithful toward a girl who was willing to dance and lip-sync her way through an entire doo-wop song at the prospect of their anniversary date (and who evidently resembled a Playboy centerfold).
* BlindMistake: Brenda, stranded in a bus station without her glasses, pets a huge rat thinking it's a lost cat.
* BlindWithoutEm: Brenda. Oh, Brenda.
* BookEnds: "Then He Kissed Me" is featured at the beginning and end.
* BrattyHalfPint: Sara has her moments.
* BrokenPedestal: Sara is heartbroken when Mr. Dawson (who looks exactly like Thor, her hero) turns out to be a JerkAss and won't let them have the car because they're $5 short. [[spoiler: Good thing he turns out be a JerkWithAHeartOfGold instead.]]
** This is Chris's reaction when she discovers [[spoiler: that her boyfriend is a total sleaze.]]
* ButtMonkey: Brenda.
* TheCameo: Albert Collins.
* CatchPhrase: "Ya think?"
* ChekhovsGag: "Stray Dog." Also, Daryl loses the Playboy he presumably stole from his dad. Also "Nobody leaves this place without singin' the Blues." Also... actually, it would probably be quicker to list the gags that ''aren't'' Chekhov's Gags.
* TheCityNarrows: The bus station, where Brenda saw three people shoot up, a bald Chinese lady with no pants, a homeless man who lives in the telephone booth she's trying to use, and a guy who keeps showing her his gun.
* CountryMouse: Just suburban, but otherwise the same.
* [[CoversAlwaysLie Covers Sort Of Lie]]: They don't scale a skyscraper, as the poster shows, but Sara finds herself stuck outside of one in the climax.
** Also, Chris doesn't wear the skirt (or shoes) seen in the poster, either.
** The [[http://www.thebestlittlefilmhouse.com/ekmps/shops/tblfh01/images/a-night-on-the-town-aka-adventures-in-babysitting-uk-quad-1988-elizabeth-shue-artwork-by-drew-struzan-11338-p.jpg international version]] of the poster removes Maia Brewton completely and replaces her with George Newbern (who is also scaling the building, for some reason) to focus on the romantic element of the story...which is only a small part of the movie.
* EasterEgg: According to [[http://www.vulture.com/2011/12/keith-coogan-star-of-dont-tell-mom-the-babysitters-dead-indulges-our-nostalgia.html an interview with actor Keith Coogan]], Elizabeth Shue is actually in the frat party scene as two simultaneous people--both as Chris and as a random girl wearing a black cap and sunglasses. This was so that she could dance as an extra while other angles were being filmed.
* EvilOverlooker: On the [[http://www.moviegoods.com/movie_poster/adventures_in_babysitting_1987.htm Japanese poster]].
* {{Fangirl}}: Sara is a big...nay, ''HUGE'' fan of [[TheMightyThor Thor]].
* HeelFaceTurn: Joe Gipp.
* HeKnowsTooMuch: That ''Playboy'' issue had a bunch of notes the gangsters scribbled down...so much, in fact, that it would send them to jail.
* HookHand
* ICanExplain: Yup, Chris's boyfriend was NOT doing what he claimed he was. He was with another girl. Although, he doesn't even try to explain. He just doesn't care. Chris dumps him, and ends up with a different guy by the end.
* JerkAss: See above descriptions of Mike.
* LittleMissSnarker: Sara.
* MamaBear: Chris, especially on the train, dealing with the gang members.
--> '''Gang leader:''' Don't fuck with the Lords Of Hell! (After he throws his switchblade down into Brad's foot.)
--> '''Chris''' (yanks the knife out of Brad's foot and points it at the leader): Don't fuck with the BABYSITTER!
* MarketBasedTitle: This was released in Britain as ''A Night On The Town.''
* MonochromeCasting: Obviously intentional in the case of the jazz bar.
* OffscreenInertia: Although it can be presumed the police eventually brought him back in and arrested him along with his boss, at the end of the movie the gangster who climbed out on the side of the Smurfit-Stone building to get Sara and the ''Playboy'' is shown still out there, clinging to the glass in terror...
* PrecisionFStrike: Two in two successive lines, resulting in the movie's PG-13 rating. See above.
* PrettyFlyForAWhiteGuy: The suburban white kids wow the cynical inner-city black audience with their improvised blues song. Though maybe they're just getting props for working under duress (what, exactly, happens to those who refuse to comply with the order to sing the blues?).
* PrettyInMink: A teenage runaway in a white fur jacket, Mrs. Anderson has a black mink coat, and Chris uses a full-length coat with a huge collar to sneak into the office party the Andersons are attending.
* RandomEventsPlot: Chris' friend Brenda runs away, has to have Chris pick her up, the car gets a flat, they get picked up by a truck driver with a HookHand, who is pretty nice until he finds out his wife is cheating on him, they end up getting in a car while it's getting stolen... It just goes on and on. See ASimplePlan below.
* RecycledTheSeries: A sitcom pilot for a TV version aired on CBS but did not go to series. The most notable actors to appear in the pilot were Joey Lawrence and Brian Austin Green as Brad and Daryl. The premise centered on Chris, Brenda, and the kids getting held up at a store, locked in a storage room, and then trying to escape through the sewers where they come face-to-face with an alligator.
* RunningGag: The Playboy centerfold.
* ASimplePlan: All Chris is trying to do is drive herself and the kids into the city, pick Brenda up, and drive back.
* TheStinger: See OffscreenInertia above.
* TerrifyingRescuer: Chris's car gets a flat, leaving her stranded on the side of the expressway. She is understandably frightened when a huge truck pulls up behind her and a hulking figure with a HookHand gets out. But this turns out to be tow-truck driver "Handsome" John Pruitt, who offers her a free tow to Dawson's Garage.
* TrailersAlwaysSpoil: The trailer pretty much walked the viewer through the film's main events, including the climax at the Smurfit-Stone building, then actually showed [[spoiler: the parents returning home and Chris sitting on the couch, safe and sound. "Any problems?" they ask, to which she casually responds, "No, not really."]]. Kinda destroys the tension.
* UrbanLegend: Chris is telling one to the kids while heading to the bus station. About the guy with the hook. Guess what the helpful tow truck driver who rescues them a few minutes later is sporting.
* WorstAid: CHRIS PULLED THE KNIFE OUT OF BRAD'S FOOT! (Okay, it was a toe, the wound only required a single stitch, and she pulled the knife out not in an effort at first aid but in order to defend him and herself from a gang. But [[spoiler:the scare where the ER doc confused them for asking about a different patient and told him "their friend" was dead, when Brad was actually just fine,]] may have been a bit karmic).
* WrongGuyFirst: Mike
* YoungerThanTheyLook: The prostitute. Or so she claims.
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