I came across this article on PSFK, on people liking Roomba's because they are like us (faulty). There is also discussion of how people are adjusting and incorporating technology into our lives by naming devices and humanizing them. This humanistic element as faulty can be seen the the 2008 Pixar movie Wall-E. The thing that makes the main character so lovable is that he is not operating exactly as programmed. He is an hyperbole today's Roomba, figuratively and literally. There are also subtexts to Wall-E that speak to the dehumanizing aspect of technology, specifically in a mechanization and homogenization of life.
The combination of these articles and meanderings reminded me the late 80s film, Robocop, by director Paul Verhoeven. Somewhere in the commentary track, Mr. Verhoeven notes that one of his goals with the film was a reaction to other films at the time that pitted man against machine. Robocop on the other hand, was about a man thrown into the middle of this evolution, who had to come to terms with himself as technology. I think a trend in films from man vs. machine to man & machine could be plotted, and we would see an increasing number of films with people coming to some kind of peace or mediation with humanity and technology (the Matrix trilogy, iRobot, Ghost in the Shell, Battlestar Galactica 2004 series, etc). The Terminator series, started by James Cameron, has a recently updated storyline through the TV show on USA (Sarah Connor Chronicles), that started to hint that in the future, not all machines wanted to destroy humans. Some it seemed would choose to aid humanity, and did not need to be reprogrammed.
What does all this mean though? I think it supports Kevin Kelly's proposition that Humanity is Technology. Sometimes in the race to extend our grasp, we get so focused on the reach, that we forget why we are reaching (there are some great thoughts and subtexts to this in The Prestige, Battlestar Galactica, and Steamboy), and extend our hands hoping to grab anything that come along. Many of the films and shows I have sited, are full of warnings of the what happens when Humanity and Technology come to an intersection. More and more stories are forming conclusions and stories about how this intersection can be resolved in a win/win scenario rather than a zero sum game.