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Feedback request on my screenplay

While I'm not the grammar/spelling police, you have lots of errors which make it not only distracting to read but in some places confusing. Secondly, the formatting is non-standard which is also rather distracting. It's good to get in the habit of writing in a professional style from the start rather than unlearn bad habits later. CeltX is free and could easily handle the script formatting automatically for you.

Getting the technical stuff out of the way, I think it was good until page 8. At that point, the dialogue and story issues became confused. You mention he smoked a cigar then later Steve notices cigarette smoke. Which is it? Blair comes across as very much an amateur. He should be able to pick a lock. Heck, if you go on YouTube you can see how to pick a lock. Using a screwdriver to climb through a window doesn't seem smart. Smoking in the vic's house also seems very amateurish. Especially if he picks up that it's not his brand. You've already established that Steve is also a hired assassin.

Next Daniel appears out of nowhere? He must have been affiliated with Steve if he was in that area. If Drake was trying to make a message of Steve, it just seems odd that Daniel would simply invite Blair into his car rather than bump him off. Tit for tat. However, once inside the car, the dialogue becomes nightmarishly dull and rambling. Then we see the bar scene. WTF? Then we move to the diner with Ruby. That's the end? It doesn't make sense to me. After page 8, the script loses its story. Please, the use of voiceover on p. 7 is totally uncalled for. You could shorten it and put that into the bedroom scene.

I'd also make changes to the scene. A scene has to have a purpose that drives the story. If it doesn't, it shouldn't be included. You want to minimize the number of shot locations to be essential to the story. Below is how you could repurpose page 5. Notice it is "lies" not "lays".
Code:
EXT. STREET - NIGHT

Blair leaves the party and walks up the lonely street again. He 
takes an alcohol canister out of his jacket pocket and gulps on 
it. 

EXT. APARTMENT COMPLEX - NIGHT

Blair walks up the stark staircase lit by naked lightbulbs.  He
lumbers to a door, drags a key from his pocket and fights 
through the exhaustion to turn the locks.

INT. BLAIR’S BEDROOM - NIGHT

Blair *lies* on his bed, sleepless as he stares into the ceiling.

                            BLAIR (V.O.) 
              Nothingness fills my days, routine the 
              bread I eat. Change is my enemy it 
              seems.

He gets up and lumbers towards the bathroom.


INT. BLAIR’S APARTMENT TOILET - NIGHT

Blair splashes a handful of water against his face. He stares
into the mirror, his face like a zombie, dead and cold. 

Opens a cabinet case and forcefully swallows vitamin pills like 
they were the cure of his life.

Placing his palms on each side of the bathroom sink, he looks 
ahead, seemingly into the drain hole.

The mirror reflects as he turns to dry his face.

The light goes out.


INT. BLAIR’S APARTMENT LIVING ROOM - DAY

The living room is a cluttered mess with mags ranging from 
the dirty type to current news all over.  Pairs of Marine Corps 
boots are far in distance like they were slung with a catapult. 
Empty cartons of cereal and sugars dropped where they were 
opened and the stickiness on the floor has transpired from 
the fall of an unsealed bottle of coke.

Blair moves about as if the state of his apartment were 
the standard of all households. He puts on his jacket and 
adjusts the collar of his raggedy jacket.  He opens the door 
and slams it as he rushes out.
Though honestly even here the voiceover isn't very important. And if push came to shove, I'd simply cut the bedroom scene. What does a guy with insomnia really tell me? By re-using the hallway, you can shoot the kids' scene and this night scene at the same time. You don't have to do a separate set up outside of the apartment complex. It's a practical consideration. Again, big run-on paragraph. If you're shooting this yourself, it's one thing. If you plan to do this professionally, be sure to always check spelling and grammar. One or two misses, most readers will forgive. But with two or more on each page, it is an immediate pass.

I think it starts a bit rough but could be fixed. But after he meets with Steve, it just quickly unravels.
 
Thanks for the critique, Sci-Fi. Greatly appreciated.

The formatting: I'm using the spec-script format where I don't include camera work or direction of any kind and just tell the story. Are there issues with that?

The story: I intend for my character to drive the story, like a character study. There's no direct plot, the plot is the actions of my character, you know?

I'll try to clean it up. I too didn't like the dialogue between Blair and Daniel in the car, I'm not sure how to write good/compelling dialogue without appearing ramble-ish.

Do you suggest I rewrite from Page 8 and onwards?
 
Thanks for the critique, Sci-Fi. Greatly appreciated.

The formatting: I'm using the spec-script format where I don't include camera work or direction of any kind and just tell the story. Are there issues with that?
You simply used centering. Actually there are fixed margins in the spec standard. There are templates you can use. CeltX, Final Draft and other programs have them built in.
Code:
| 1 ½” left margin                                1” right margin |
|<---  2 ¾” tab -------->|CHARACTER
|<---  2” tab ------->(Parenthetical)
|<---  1¼”  -->|Dialogue      stops by   5” mark |
When you simply use centering, large dialogues get confused with action lines. And also, as a director/producer, when you follow proper formatting, the timing works out more closely to one minute per page and helps for budgeting time for shoots. If you break your paragraphs into visual scenes, it makes migrating to the shooting script easy. And if you're not a director/producer, it allows them to visualize shots more easily.
The story: I intend for my character to drive the story, like a character study. There's no direct plot, the plot is the actions of my character, you know?

I'll try to clean it up. I too didn't like the dialogue between Blair and Daniel in the car, I'm not sure how to write good/compelling dialogue without appearing ramble-ish.
I appreciate what you want but the difficulty is there is no end point. Films need to have an end. Audiences want some sense of closure.
Do you suggest I rewrite from Page 8 and onwards?
I think you need to have an ending in mind and let your character wind his way towards it. I suggest that if you want to end with Ruby, you should also start with her. It doesn't mean she talks with him, but it introduces her.
Code:
INT.  RESTAURANT - NIGHT

A young waitress, RUBY (20s), pours coffee behind a bar.

BLAIR HANDEN (mid 20s) in his raggedy jacket, cowboy 
jeans and boots sits at table picking at his food.  He 
glances out the window.

Ruby comes up to fill his coffee.  He looks up and waves her
away.  She smiles and walks to another table.

Blair's cell phone rings.  He looks down and sees "Drake".
He sighs, slips it back into his pocket, and pulls himself out
of the booth.


EXT. STREET - NIGHT

A dark, empty street illuminated by the bright street 
lights.

Blair walks down the street and enters a seemingly quiet 
building, steadily checking himself.
...
Now you have set up a reason for the ending having some meaning. After page 8, why would Steve leave a hot girl? Have him have to take a call from Daniel. Have Steve deliver some of your "message" as a proxy. On the phone Steve explains to Daniel the importance of having a life. (1) It makes Steve's death all the more poignant (life's short). (2) It gives a reason for Daniel to be in the vicinity. (3) Hearing Steve talking to Daniel gives Blair stuff to think about. Now Daniel can approach Blair but rather than being friendly, he needs to be more aggressive. Drake is going down. Daniel says he can use a man like Blair or he can be taken out. I'd have Blair pushed onto the sidewalk from the car in a beaten state. Ruby sees the car drive out and she runs out. She helps Blair inside and gets him coffee. Now for the first time, he sees her. Now they have a meaningful dialogue. I'd contrast Blair and Ruby with Steve and the Floozy.

What you need to do is develop your characters. And one way you can do that is through contrast with other characters. Since Blair is so emotionally dead, you need to show that and the gradual change. We get a hint with the kids but even there I might play with it a bit having the kids playing cops and robbers. As a writer you need to be thinking about symbolism. What do you want the audience to take away? How will it end?

At the moment, you've strung scenes together with very little connection. There needs to be a reason why things happen. Sometimes that's by direct action and dialogue, and sometimes we demonstrate by background events and symbolism. But by tying together the beginning with the end, you show how something meaningful is opening up for him.
 
The formatting: I'm using the spec-script format where I don't include camera work or direction of any kind and just tell the story. Are there issues with that?

He's not talking about spec-script vs. shooting script. You should definitely be writing a spec script, but the problem comes in the way that it's organized. Google screenplay formatting, or read a screenplay, and you'll see what we're talking about. The text should never be centered for one thing. For an easy fix, you could just use a free screenwriting software (my personal favorite is Adobe Story).

Also, the script is fulled with sentences that give confusing imagery. For example, "Blake signals NO with his head and face." What does that mean? How does one say "no" with their face? If you mean to say that he shakes his head, just say "Blake shakes his head." This isn't the only one, it's just the one I picked out. I would just go through and fix any like this.

Why do you wait until page 7 to introduce the V.O.? Really, you should introduce it at the start of page one, or at least somewhere on pages one or two. Until the point that you introduce the V.O. it's more or less in third person limited. By introducing the V.O., you change it to first person and the effect is jarring and confusing.

Lastly, I agree with FSF's point, he should know his business. Learn about the trade that he's involved in, the shape his actions and dialogue around A) his character and B) his profession.
 
The great advice still stands but I neglect to mention that the script is not a short, it's intended to be a full-length feature (90 pages or so).

Symbolism is definitely important, I'm not sure if you caught it but in the beginning, Blair walks on a lonely street thus reflecting his character. Trying my hand at stuff like this, it's hard.

Don't know if this'll mean much to anyone but I'm having much trouble filling up the meat in-between my major scenes. I need to reveal the plot to show what I mean, can I?

PS: I'm downloading CeltX as of this moment.
 
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