Between 1984 and 1986 the top five best teen movies IMO from the 80’s came out, maybe even of the 90’s as well. They might have some competition with American Pie trilogy. The past few days I’ve been watching these films. I’m sure that you can probably guess at least 3 if not all 5 without even reading any further. Please note that these are in no particular order, although I think if I absolutely had to pick one as my favorite, it would be sixteen candles. (Screenshots were personally done by me for this post)
Sixteen Candles
1984 – Written and Directed by John Hughes
Summary: Samantha’s life is going downhill fast. The fifteen-year-old has a crush on the most popular boy in school, and the geekiest boy in school has a crush on her. Her sister’s getting married, and with all the excitement the rest of her family forgets her birthday! Add all this to a pair of horrendously embarrassing grandparents, a foreign exchange student named Long Duc Dong, and we have the makings of a hilarious journey into young womanhood.
“Can I borrow your underpants for 10 minutes?”

Pretty in Pink
1986 – Written by John Hughes, Directed by Howard Deutch
Summary: Young Andie is one of the not-so-popular girls in high school. She usually hangs out with her friends Iona or Duckie. Duckie has always had a crush on her, but now she has met a new guy from school, Blane. He’s one of the rich and popular guys but can the two worlds meet?
“You said you couldn’t be with someone who didn’t believe in you. Well I believed in you. I just didn’t believe in me. I love you… always.”

The Breakfast Club
1985 – Written and Directed by John Hughes
Summary: It’s the weekend, and five students have weekend detention. There’s a jock, a princess, a misfit, a nerd, and a lout. Not much in common, except for having to give up their day, sit in the school library, and write an essay for the principal. Being from such widely different backgrounds and having such completely different personalities, it’s inevitable that some frictions and shenanigans develop. Especially when the principal leaves the room.
“Naked blonde walks into a bar with a poodle under one arm, and a two-foot salami under the other. The bartender says, I guess you won’t be needing a drink. Naked lady says..” the ceiling gives way “Oh, SHIT!!!!”

Weird Science
1985 – Written and Directed by John Hughes
Summary: Two unpopular teenagers, Gary and Wyatt, fail at all attempts to be accepted by their peers. Thier desperation to be liked leads them to “create” a woman via their computer. Their living and breathing creation is a gorgeous woman, Lisa, who’s purpose is to boost their confidence level by putting them into situations which require Gary and Wyatt to act like men. On their road to become accepted they encounter many hilarious obstacles which gives the movie an overall sense of silliness.
“Gary?… By the way, why are we wearing bras on our heads?”
“Ceremonial.”

Ferris Bueller’s Day Off
1986 – Written and Directed by John Hughes
Summary: Ferris is a street-wise kid who knows all the tricks. Today he decides to take the day off school. When Ferris takes the day off, so must his best friends, Cameron and Sloane. Cameron is reluctantly persuaded to borrow his father’s Ferrari, and together they hatch a plan to get Sloane out of class. Suspicious dean of students Ed Rooney knows all about Ferris, but can never catch him. Ferris’ sister Jeanie is also frustrated that Ferris always gets away with his tricks and she doesn’t. Furthermore, Ferris is an ‘angel’ in his parents eyes. It’s Ferris’ day off, he’s out to enjoy himself, and he does!.
“Ladies and gentlemen, you are such a wonderful crowd, we’d like to play a little tune for you. It’s one of my personal favorites and I’d like to dedicate it to a young man who doesn’t think he’s seen anything good today – Cameron Frye, this one’s for you.”

As you can see John Hughes was/is “the man” and a very busy man from the looks of it as these were all written by him and he directed all but one of them, and all with in a couple years.
The plot summaries for these movies was borrowed from IMDB