Hi, Kevin,
Is this your first script posted on the site? If yes, then welcome. If no, then also welcome. Since you asked for feedback on the script, here are my thoughts.
First about the writing.
Quoted Text INT. PRISON SHOE WORKSHOP - DAY SUPER: MISSOURI STATE PENITENTIARY, 1899
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Just a nitpick. Usually, the SUPER is written to the left margin of the page. Aligned with the slugline.
Quoted Text INT. PRISON - DAY
Jeffers leads Harry back to his cell, stopping at the prison commissary to pick up his outgoing clothes along the way. As they arrive at Harry's cell, Jeffers opens the cell door.
INT. OUTSIDE HARRY'S CELL - DAY
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The second slugline is a bit confusing and at best, you don't need to write it that long, use a mini-slugline. Just go,
INT. PRISON - DAY
Jeffers leads Harry back to his cell, stopping at the prison commissary to pick up his outgoing clothes along the way. As they arrive at-
OUTSIDE HARRY'S CELL
Jeffers opens the cell door.Another issue is, there are many SUPERs in the script.
Quoted Text WARDEN Take him back, Jeffers. Fix him up with outgoing clothes and unlock him at 7 in the morning. Then bring him to the bullpen. Consider thinking over my advice, Higgins.
JEFFERS 7 a.m. Be ready to go.
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The above two dialogs inform us that Harry will be released at 7 a.m. So you need not to inject-
Quoted Text INT.PRISON CLERK'S OFFICE - DAY SUPER: 7:15 THE FOLLOWING DAY
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-the SUPER here. The audience will see him out and understand that it is/after 7 a.m.
Quoted Text EXT. OUTSKIRTS OF JEFFERSON CITY - DAY - WALKING
EXT. JEFFERSON CITY - DAY - WALKING
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Walking is an action. So write it in the action lines, not the slugline.
Quoted Text After some time, Harry passes the local church and sees what he's looking for: A restaurant.
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Screenplay should be visual so don't write what your character is thinking or in this case what he is looking for. Only write visual stuff.
Quoted Text The train slows to a stop at the Ozark station and Harry stands up and walks to the now open exit door. He exits the train and heads towards town.
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You can condense it a bit. You may write it-
The train stops at the Ozark station, Harry exits the train and heads out. -like this. Write short and crisp.
About the story.
I know O Henry ( William Sydney Porter) and read his story 'Witches' Loaves' but never read this story. So my comment will be purely based on this script.
The story at the start is clear but in the middle, it wobbles a little. The conversation between Davey and Harry on the script page 15 is little off-putting, I think Davey helps Harry in some way to get him out the prison. At the end, Harry comes out as a good samaritan by saving the girl's life.
The dialogs were really nice. They were voiced to give Harry and Davey individual personality.
All in all, a nice story just the writing needs some fine-tuning.
I hope this helps. If not, I hope other members chime in.
Good luck.