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This was a quick read for me, but ultimately, I think it works more for me in some areas than others.
I thought the beginning was terrific. I could definetly see the V.O. between Chance and Lily over black before revealing Lily tied up in the chair. It was a nice, quick hook for the reader IMO.
You lost a bit of my attention when you started toggling between the three apartments. After reading, I understand why you needed to do so, but I don't think that I ever really felt a strong connection with any of the three captives. I'd like to see you maybe have Chance illicit more of a reaction from each of them in order to entice the audience a bit more.
So, ultimately, I guess I was a little confused by Chance et al. motives for doing what theya re doing. I mean, I guess I see that they are trying to make people seize their opportunities while they still have thme, but I don't necessarily see how this connects with the Ghost Boy (i.e. Chance).
Also, I'll give you Lilly's participation as she is Chance's gf/wife/lover, but why does Josh go along with this? I understand that this may be a lot to try and fit into a short, and that not every plot line is goign to be airtight (trust me I get this from personal experience), but I think you might be able to explore some of these issues to the overall benefit of the story.
Lastly, the line where Josh says to Catherine something along the lines of "Promise me you'll do something good with your life, kid" struck me as odd since she is late 20's and he is early 30's. Maybe make him a bit older than Lilly and Chance.
Anyway, like I said, some of this worked really well for me, and I think you have a decent idea, but I also think that some of it could be fleshed out a bit for me. Anyway, good luck.
TJ, I don't quite "get" this idea. Threatening people's lives to be inspired? If I was Catherine the first thing I'd do after they left is call the police. And besides what if the trio (J,C&L) went to someone who didn't want to be inspired? How do they know who to visit?
Also the scenes when Chance visits Josh and Lily alone are pointless, the fact they are tied down isn't done to convince anybody...apart from the audience, which is aside from the point.