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I apologise for not reading everything above in depth.
I found your script to be entertaining. I enjoyed it. I agree with your comparison to Rounders. The reason to win money was to clear all his debts. A reason to gamble. What was driving Michael to persuade Vinny?
What I was thinking at the end was what happen next? I think you should do another short.
Good story. I love Rounders and gangster movies, so this story was a great mix. Like a lot of the other responses, I had a problem with the end. There was build-up with Michael's torture, but not on the game. With most of the story revolved around poker - even the title - I expected poker to be a bigger presence. That's actually was drove me to the story. I would've liked to see the end unfold like this - Vinny and Tony are playing, Vinny's acting strong and Tony is buckling, slightly. You played up the game to a point - we didn't see their hands. So at the end of the hand, Tony reluctantly calls with a straight, and Vinny was bluffing. 7-2 offsuit. Vinny laughs, turns to yell at his thugs "check this out. He gambles his brother's life on shit!" He turns back around, Vinny's already in his face, just about to knock him over. This would catch Vinny more off guard, his thugs, too. Maybe Tony's gun was on the table and Vinny grabbed that. Minor shoot-out with his thugs. Same ending, little more believable, and uses Vinny's poker skills described earlier in the flashback (but not implimented) and adds more suspense.
Just suggestions, obviously. After reading through, I thought of this scenario. Also, I liked the VO and would've liked to hear it a little more and I think the flashback was just fine. Maybe some more details on the heist and why Tony would play with Vinny, but in a short it may be irrelevant.
Great job, keep the scripts rolling.
Why is a Raven like a writing desk? onus - Three men, three guns, no escape. (WIP) the Deal - What would you do for a million dollars?