Adventures in Babysitting (1987)
Not what you were expecting to follow Roman Holiday, right? Think about it - yes it's a comedy filled with action, adventure, crime, and the babysitting blues, but it also starts with a teenage boy, Brad (Keith Coogan), with a crush on his babysitter, Chris (Elisabeth Shue) - well technically his sister Sara (Maia Brewton)'s babysitter. Chris, of course has a boyfriend (Mike, in one of the few times we root against Bradley Whitford) and Brad's best friend Daryl (Anthony Rapp) likes to paint Chris as a doppelganger of a pinup model.
If you can't tell, Chris has her pick of guys - though some are not desirable. Though in all seriousness, what's not to love? From the first title credit you will find yourself smitten with her as well. Can we take a moment to reflect how I learned all my sweet dance moves from the opening credits?
What should have been a quiet babysitting gig turns into a whirlwind thanks to Chris' best friend Brenda (Penelope Ann Miller) deciding to run away from home with no real money to her name. Chris agrees to come to the rescue, but has to do it with Brad, Sara, and Daryl tagging along. What could go wrong?
Well let's see: flat tires, getting mixed up with Chicago's shady underbelly of carjackers, street gangs, gun fights, Vincent D'Onofrio as Thor (technically Dawson), forced to sing the blues to escape said shady underbelly of Chicago, and frat parties--just to name a few. Through it all, Brad hopes to win the girl. He proves he is better than Mike... grrr Mike! But he wasn't expecting the college guy George Newbern to enter the scene. Personally I would have ditched them all for Thor... but that's just me.
Escaping death threats (literally) and barely making it home before the parents arrive only solidifies the fact that Chris and Brad are friends..... like Duckie and Andie, but without all the style. Is Brad a bit crushed? Yes. Does Chris feel a bit bad? Of course. No one wants to hurt their friend's feelings. It completely sucks not getting the girl, especially being stuck in...DUN DUN DUN... The Friend Zone. However, the last scene shows that Brad will be okay, because he wants his friend to be happy. Plus they will always have these moments to laugh about throughout the years to come.