Anthony Townsend teaches urban planning and interactive design at New York University and is the Executive Director of NYCwireless, a non-profit organization that aids the development of open public wireless networks.
For Praxis he has written a nicely illustrated overview of four of the world's most digitally-mediated urban spaces: Times Square, Shibuya Crossing in Japan, Union Square in NYC, and the proposed Digital Media City [DMC] in Soule. He suggests that:
To begin thinking about potential reconfigurations of urban space, it is useful to consider the relevant applications in which digital technology has advanced significantly in the last decade. Broadly, we can group these technologies into four groups based on their functional application in urban environments: display and expression, communications, positioning, and documentation. [My emphasis.]
Imagine having all of Times Square as your palette.
Townsend is also involved in designing Digital Media City, along with a team from MIT. More on that here. [Via Smart Mobs]
As for Times Square, Yahoo just turned one of the area's biggest signs into a videogame that you can play from your cell phone on the street. "The game is kind of like those old Hot Wheels games where you set up the track and just control the speed of the car, with no steering."