Judgement Call: Casting at Fish You Might Not be Able to Land

This video from of Jazz and Fly Fishing begs the question that I'm sure most of us have come across at some point in our fishing careers: Do you cast at fish that probably aren't land-able from a bridge, pier, or any other abutment above water?

I'll be honest; when I'm in one of these situations, I typically take a look around and tell myself that while not probable, there might be a way to land said fish. It's a bad idea most of the time. Either the fish gets a piece of face jewelry or I lose a leader and occasionally the fly line. On the other hand, it's almost always a miraculous feat if manage to you pull it off--and you will cheered on by any fishing pals nearby.

What do you think? Is this poor form or a fishing feat?