While posing as a street person at night to scam people, a conniving ad executive is faced with his greatest fears when he loses everything and becomes homeless himself!

If he was trusted with money to give to the homeless but instead was splurging on himself (casino,women,drugs) it would be poetic justice if he ended up homeless. Many factors could make the inciting incident. Then perhap we could see the high rolling executive transformed to a more compassionate, humane person that everyone suddenly admires instead of deplore. Then he can get his old position and ideally make this world a better place.

Sounds like a pretty solid drama. My only question is, why would an ad executive need to appear homeless to scam people - surely there are better, subtler ways that would have better payoffs? If it wasn't for the rest of the logline I'd assume this was a comedy because of that part. However, I really like the premise, and if you're able to pull of that question satisfactorily, I'd go for it.

Good suggestion. And sadly, I saw Trading Places in the theatres when it came out! lol