Matt Jones, creator of many useful ideas including warchalking, has a wonderfully titled and fascinating essay up on IO9: "The City Is A Battlesuit For Surviving The Future," that examines the futures of cities that respond in realtime to their inhabitants.
Which leads me back to science-fiction. Warren Ellis created a character called Jack Hawksmoor in his superhero comic series The Authority.
The surname is a nice nod toward psychogeography and city-fans: Hawksmoor was an architect and progeny of Sir Christopher Wren, fictionalised into a murderous semi-mystical figure who shaped the city into a giant magical apparatus by Peter Ackroyd in an eponymous novel.
Ellis' Hawksmoor, however, was abducted multiple times, seemingly by aliens, and surgically adapted to be ultimately suited to live in cities – they speak to him and he gains nourishment from them. If you'll excuse the spoiler, the zenith of Hawksmoor's adventures with cities come when he finds the purpose behind the modifications – he was not altered by aliens but by future humans in order to defend the early 21st century against a time-travelling 73rd century Cleveland gone berserk. Hawksmoor defeats the giant, monstrous sentient city by wrapping himself in Tokyo to form a massive concrete battlesuit.
The City Is A Battlesuit For Surviving The Future