John Cusack and Patrick Dempsey made the best summer-time movies IMO.
Dempsey:
Can't buy me love
Loverboy-my favorite by far
Brighton beach memoirs
Cusack:
Better off dead-another great one
The sure thing
One crazy summer
Sixteen Candles
Say anything
They both went on to make many more good movies, but these early ones were at the time I was growing up, so many, many good memories.
If anyone has not seen Loverboy, I highly reccommend finding it and watching, it really is a good old 80's comedy, well worth the time. And add Better off Dead to that list.
To add, there is a very early Tom Cruise film (1983) called Losin It. It is about 4 guys going to Tijuana to lose their virginity. An entertaining movie I have been trying to find for awhile now.