Can we have a montage of getting ready for a date while Walking on Sunshine plays?
Oh indeed.
Let’s also get a montage of the main girl getting over a bad break up by going out and having fun with her friends (nail salon, ice cream, shopping) while The Sign - Ace of Base plays, as well.
Or perhaps the ugly duckling in the group gets a makeover and is gasp actually a beautiful young girl.
There’s going to be a fight or a showdown at some point. Cue the theme from The Good, the Bad, and the Ugly.
Plucky underdog/comic relief is going to have to man up and save the day… Bonnie Tyler - I Need a Hero to the (ironic) rescue!
As we zoom in on one of the main characters who is coming to the realization that he’s made a huge mistake, we hear the opening notes of Sound of Silence.
I dunno what kind of bad movie we’re putting together here but it sounds like it just got a lot more interesting 
If I can tweak that a little: the protagonists get high and we heard Sunshine of Your Love as the drugs kick in, then they find themselves in the middle of a political protest as For What It’s Worth plays, then the demonstration gets violent to the strains of Gimme Shelter, and the next thing they know they’re in Vietnam as we hear All Along the Watchower.
Naturally, when someone has to make a mad dash somewhere, we hilariously cut to slow-mo, and cue…Theme from Chariots of Fire. Which will be recognized by more people than actually saw the original movie.
And I believe the canon for “Hueys-cruising-over-'Nam” music is:
**For What It’s Worth
Fortunate Son
All Along the Watchtower
Paint it Black
Run Through the Jungle
**
Ride of the Valkyries, of course, has transcended this to appear in all movies when something flying is attacking something not, down to the level of flying squirrels.
But then she and her boyfriend get back together, spending a day at Coney Island. When they duck somewhere private to make out “Under The Boardwalk” plays.
A heavy metal version of Tocatta and Fugue in Dm for that scene with the old house where the school caretaker (widely rumoured to be an axe murderer) lives.
A flying squirrel attack set to Ride of the Valkyries would be worth the price of admission by itself.
New Found Glory – wait, it’s not them, they just did a cover.
And when he’s taking a walk to think about the huge mistake, perhaps skipping stones or walking past children in a playground, you hear Mad World.
Born To Be Wild the second anyone gets on a motorcycle.
Hello, I Love You for when the male protagonist first spots the female lead walking down the street (or beach) in slow motion.
Not a song, but don’t forget the steel guitar flourish+vulture squawk for any scene taking place in the desert.
It’s by Sixpence None The Richer.
And to contribute to the thread:
Our intrepid heroes get a flat tire on a highway somewhere in the Deep South. Cue Dueling Banjos.
…but the character that comes up on them is actually from the Caribbean! Every little thing’s gonna be alright, or so sez Bob Marley.
Something like this was done in the movie Rango with the goofy redneck moles flying on bats. I thought it was done pretty well but I liked that movie a lot more than some people that I know.