What should I include in my "Pocketful of Poses?"

I'm making a BIG POT OF CHILI and wondering what songs I would include on a soundtrack for a 1980s teen film. You know, like a John Hughes film.
I burned a MIX CD back in 2003 (*seven* years ago? I can't believe it) called "POCKETFUL OF POSES: A SOUNDTRACK FOR AN IMAGINARY 80s TEEN FLICK" that included a bunch of tunes that would sound great in a 1980s film, including "I Touch Roses" by Book of Love, "Blind Vision" by Blancmange and "Annie, I'm Not Your Daddy" by Kid Creole & The Coconuts.
The problem with the CD is that because of its format, it's limited to just over an hour of music -- and everybody knows a 1980s teen film should have two hours of music.
That's why I'm trying to decide what other songs I should put into my imaginary teen film
playlist on my iPod.
What should I include?
I want a Go-Go's song in my mix, but not one of the really popular ones. I'll go with "This Town" from "Beauty and the Beat" instead. It weds punky energy with girl-group melodies -- a perfect representative song for the Go-Go's.
I want a couple songs from the "World Machine" album by Level 42. Barely remembered today, Level 42's funky new-wave style sounds cinematic nearly 30 years later. Sure, the production tricks place the album squarely in the 1980s. Who cares? It's an imaginary 80s film I am trying to back with tunes.
There should be something with a definite edge on the soundtrack. I always thought the inclusion of these gritty, "punky" songs were used by filmmakers to give themselves a feeling of "street cred" with any Rayban-wearing hipsters who happened to see the film. I'm going to pluck a 4 Skins song from obscurity. I had an album by the pioneering Oi band back in the day, and their violent songs would give any teen movie soundtrack loads of street cred.
I'm going to include "I Predict" by Sparks, too. Why? I just love that band, and they didn't appear on enough soundtrack albums.
There always seemed to be one "older" song included in these soundtracks (if it wasn't completely filled with new wave). I always thought these songs were included to appear to an older sibling or parent who was dragged to the teen film by the youngsters.
For my older song, I am picking "Winter Time" by the Steve Miller Band. It is an atmospheric gem -- perfect for a scene featuring the dewy eyed starlet of my pretend film. This selection of songs could take all day. Good thing I have a lot of chili to make.