John Hughes' Spiderman

Inspired by a couple of different articles talking about "Marvel looking to get a broad, John Hughes/high school comedy vibe" for their new Spiderman series:

What if John Hughes had directed one or more Spiderman films in the 80s or 90s? (Take your pick). I think it could be fun to have a 4-set series taking place in each year of High School for him (once again inspired by rumors surrounding the new Spiderman films).

Here's are list of some movies he did in the 80s
1983: National Lampoon's Vacation
1984: Sixteen Candles
1985: Weird Science, Breakfast Club
1986: Ferris Bueller's Day Off, Pretty In Pink

I think it could be fun to see frequent Hughes-collaborator Anthony Michael Hall as the titular webslinger who is actually the exact age of high school aged Peter Parker in these movies. Another frequent collaborator, Molly Ringwald could maybe pass as Mary Jane / Gwen Stacy depending on which one you do. There's also Matthew Broderick who might make a good Norman Osborn (introduced in the fourth and final film).

The only real problem here is special effects, but for the sake of a fun discussion maybe we could talk about an 80s John Hughes directed Spiderman quadrilogy?
 
Here's where I am at:

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Spiderman Freshman Year (1983) ~ Spider-Man's origin story, Otto Octavius is the main villain, introduce Flash Thompson (full-on bully), Gwen Stacy (with lots of unresolved sexual tension), and Herman Schultz (Peter's nerdy best friend).

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Spiderman Sophomore Year (1984) ~ Peter's science teacher Kurt Connors as the main villain, Peter asking Gwen to prom (finally, YAY!), and at the very end Peter joins the Daily Bugle to help Aunt May with the bills. Flash still pretty full-on bully and Herman creates the Shocker gauntlets and tries to rob a bank.

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Spiderman Junior Year (1985) ~ Peter and Gwen begin dating, Kraven the Hunter begins his great hunt for Spider-Man, who after some initial losses discovers the Venom symbiote and sends Kraven packing. Peter struggles with juggling his job, relationship, school, and Spider-Man so the symbiote helps him cope to the detriment of his relationships. Flash loosens up and is not antagonistic to Peter but it's clear they still hate each other. At the end of the story Eddie Brock gets the symbiote and Spider-Man faces Venom. Then Peter and Gwen reconcile. If it's not too crowded try to introduce the Black Cat during this film.

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Spiderman Senior Year (1986) ~ We open with a shot of a destroyed New York City, and follow a group of paramedics as they drive through town picking up people. Everyone complains about how much Spider-Man sucks, and at the end of this sequence they pull a really beat up dude out of the back of the vehicle. "What's your name, sir?" (so they can mark him found) "Peter Parker." < And that's our cold open, the rest of the movie follows the Rise of the Green Goblin, introduces Harry Osborn (who befriends Flash and Peter, forcing them to become friends), and the Death of Gwen Stacy.

Sinister Six (1990) ~ The attempt of a gritty 90s sequel, not written by the original people. Has Doc Ock, Shocker, Kraven the Hunter, and three characters who were earlier introduced as a team of bank robbers. This one's a crazy action movie and kills the franchise until Sam Raimi revives it in the early Noughts.
 
Peter Parker's Day Off would make a good flick.

How about Lance Henriksen as Doc Ock? Vulture? Electro? Green Goblin?

Who would make a good Jameson in this scenario?
 
Peter Parker: [closing narration] Dear Mr. Coulson, we accept the fact that we had to sacrifice a whole Saturday in detention for whatever it was we did wrong. But we think you're crazy to make us write an essay telling you who we think we are. You see us as you want to see us - in the simplest terms, in the most convenient definitions. But what we found out is that each one of us is a brain...
Flash Thompson: ...and an athlete...
Liz Allen: ...and a basket case...
Mary Jane Watson: ...a princess...
Harry Osborn: ...and a criminal...
Peter Parker: Does that answer your question? Sincerely yours, the Breakfast League.
This is 80's John Hughes, right? His movies started to drop in quality after Home Alone.
 
Peter Parker moves in with Uncle Ben and Aunt May in Suburban Chicago. He attends an angsty high school, where he falls for Mary Jane Watson, the popular cheerleader who's dating the high school football quarterback.

While on a school field trip, Peter is bitten by a radioactive spider and begins experiencing side effects. Eventually, he becomes Spider-Man and breaks from the confines of his safe, quiet suburban neighborhood to the Mean Streets of 1980s Chicago.
 
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