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!
Obviously, your target is the irony of the situation; very similar to Eddie Murphy’s “Trading Places” which may be before your time. It is a stretch to think someone would go through all the trouble to “pose” homeless in an effort to reap in tens of dollars a night, when he is a successful ad excutive making tons of money (or should be). I might re-consider his motive for posing homeless. That being said, the phrase “loses everything and becomes homeless” is redundant. “…faced with his greatest fears when he actually ends up homeless.”, or “…actually loses everything he has.” You cut it down by several words, freeing up that valuable real estate that is the logline.
Just a thought…
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.