One thing that comes up for me in asking if a piece of art or an event is Win-Win in nature is how heavily mediated is the experience?. I often assume that technology or media leads to alienation and that any artist working with those tools has to constantly battle against this. The post below about Second Life I think speaks to that concern.
Then every once in a while I come across something that reminds me that some technologies actually encourage people's awareness that they ARE participants. In fact, some technologies actually empower people to be participants. I'm sure my Geek friends out there are shaking their heads (and not just at the rudimentary nature of this blog), but for me with my intense Luddite tendencies this can still be a pleasantly shocking epiphany.
Many years ago, as a small child in San Francisco, I probably danced in front of one of Ed Tannenbaum's computers at the Exploritorium. Ed designed these programs to help dancers become painters.
His video art is dated to that juuuuussst right age so that they are now exceptionally beautiful. It's not hard to imagine the pleasure of being able to move in front of one of his monitors and see colors and shapes exploding in unique patterns, each the result of your very own expression. We still see technologies that actually allow us to play and create in new ways, and it's the earnestness of people like Ed's vision that makes these technologies not alienating, but revelatory.
In a sense, Ed's work is just a continuation of this technology.
Hardly novel, but humanity's innate and supposedly unique ability to be Narcissus also means that we are eager to look at ourselves in new ways. As we explore our exterior self, our own interiority is revealed.