I like this idea.

I think you have a good collection of characters although, for an Alexander Payne style of thing, I’m not sure I would bother with the sheriff. This is just my personal preference. It’s a bit cliche in this kinda thing and makes it feel a little cartoony or too comedic. This should be about them all looking forward without being able to look past their past. Maybe the only people who are actually really bothered about their criminal past are themselves and this is their internal journey?

What I really wouldn’t want to see, is them turning back to crime at any point.

What does the protagonist learn? What’s his arc? These three need to teach our protagonist (and potentially his wife too) something about love. I’m wondering if, thinking out loud, these three ex-cons all have different relationships that need fixing. Malkovich wants a girlfriend, Woods needs his relationship with his daughter fixing, and Liotta needs to reconcile with his wife? There’s a lot of life lessons there and, in my head, it’s more interesting that they’re all different aspects of love.

The John Malkovich type – he’s brilliant with women… so what does our protagonist have to do?

I wonder if the David Hyde Pierce character should actually be someone who our protagonist aspires to be rather than him wanting to be one of the guys. This gives our hero the “looking forward” perspective – the aspirational contrast to the blast from the past he gets from his prison buddies. As this is the B-Story for our protagonist, the Act II climax could be the discovery that his neighbour also has a hidden criminal past or something? Throwing stuff out there.

Have you seen “Silver Linings Playbook”? I see this having some similarities with that film.