Better Off Dead... (1985)

Sure John Cusack might have cut his teeth in some smaller roles, but this 80s classic, Better Off Dead... (1985) was the first starring vehicle for him that made him a star.  Well this and The Sure Thing (1985), but either way you split it, this slapstick 80s ski comedy was the blueprint for a good amount of teenage romantic comedies to follow.  We follow the awkward and head over heels in love with his girlfriend, Lane Meyer (John Cusack) in their last year of high school.  Unexpectedly though, she dumps Lane and he goes into an absolute tailspin, attempting to kill himself time and time again, without getting much notice from anyone around him except for the new foreign exchange student from France who moved in next door, Monique (the ever adorable Diane Franklin).  As she falls deeper and deeper for Lane, he attempts everything in his power to win back his girlfriend, who has since moved on to a new guy, who just happens to be the best downhill skier in town.  So Lane decides that he MUST beat this guy on the slopes to win the hand of his girl back!  The only problem is his car is a broken down piece of you know what and he's just an OK skier...  That it until Monique (who happens to be an excellent mechanic and skier) decides to help him out in his predicament!  Along the way there is no shortage of 80s slapstick hilarity out of this classic, including Cusack accidentally ripping off, Tina Littlewood's cheerleader uniform while she rollerskates past him making sure you don't have any "little wood".  Ah, they truly don't make them like this anymore and the dark humor/slap happy approach to teenagers in love is a lost art form, so definitely check this one out because it's got everything you look for in an 80s flick!