Forget what you are hearing or reading as the case may be today about Jessica Simpson and a Pretty Woman remake. It isn't going to happen. EVER. The film still does incredibly well in DVD sales and no one wants that cash cow to be interrupted or sidetracked by some Jessica Simpson fiasco. No matter how much Pimpa might want his daughter to portray a hooker, it isn't going to happen.
However, the studios are willing to destroy another movie, so who the hell knows what any of them are thinking. The Grease Country project has cleared some more development hurdles and is almost a sure thing at this point. Producers are confident that despite the straight to DVD acting abilities of Jessica Simpson that in a musical, she will do very well and that people will not be as focused on her acting, but instead on her singing ability. With a strong cast surrounding her, and the recent success of the High School Musical franchise, producers want to begin filming as soon as possible.
There is still no one attached to the project other than Jessica, and Willie Nelson as the Frankie Valli character, but with the additional financing that was secured, some new songs for the film and a desire to get the project done, casting is supposed to begin in earnest.
From what I understand, Jessica would be the fish out of water character and moves to a small southern town from the big city, and hooks up with Danny there. Locations are currently being scouted in North Carolina and Tennessee for the film.