Fact: most montages in spec screenplays are dull, predictable and/or unnecessary. That's why they get a bad name as a storytelling device. End of.
Montages I see most often are changing rooms, characters cooking some kind of sumptious meal or changing seasons (usually through a window) or urban development across a city on the horizon. In other words, the spec writer is simply trying to hammer home a mood or passing of time, without actually fitting it into the context of the overarching story. Yes of course sometimes it *can* work, but like so many things in this screenwriting malarkey, sooooooo often it doesn't. With so many montages, you could literally highlight them, cut them and the next reader would never even know it had been there! Scary thought, because this basically means there's a chunk of your screenplay that is COMPLETELY INEFFECTIVE.
A good montage PUSHES THE STORY FORWARD and contributes to the story as a whole. The "let's prepare to fight" montage is a staple of horror and thriller: after a panicking and fleeing in the first half, the protagonist and friends will take stock and gather their resolve/weapons for the second half where they kick ass. In comedy, a character (usually the protagonist, but not always) may go through a number of trials and tribulations somewhere in the narrative (usually the first half) that marks them out as a loser or in need of help in some way. Detectives and investigative reporters may follow a montage of leads that go nowhere in other stories/genres and so it goes on.
In other words then, MAKE YOUR MONTAGE COUNT. If you find yourself saying, "there needs to be a montage here because I need to signify the passing of time [for whatever reason]" ask yourself if it's because you're obsessing over timeframe too much:
- Yes, in reality certain things take a certain amount of time... Even a mega whirlwind romance takes several weeks before marriage is considered without being WEIRD, but do you really need to have a montage about said couple having a wonderful time together when drama is about conflict?
- Then there are the obvious things that cannot be changed: pregnancy takes nine months, that's a fact. But do you REALLY need to have a montage at the midpoint for no other reason than to ensure your pregnant protagonist goes from her first to third trimester? Really?!
It is important to remember a screenplay is NOT reality, but a representation of it. I've seen many great films in which passing of time is signified without the use of boring montage that does nothing but pass time. Think of American Psycho: it jumps from Christmas to Easter - three whole months at least - *just like that*. Did you even notice?
I bet you didn't.
So think of montages less about PASSING TIME and more about ADDING TO STORY.