What does it take to be “The Last Best Place on the Internet”? While billions of people read Wikipedia every day, most are unaware of or do not understand the massive collaboration happening behind the scenes, involving people and machines. This collaboration is what allows Wikipedia to remain free and open source. Our vision is to host a participatory art installation in the streets of San Francisco, where a large canvas will be set up for participants to collaboratively create an art piece. Participants will be allowed to choose roles that mimic volunteer roles on Wikipedia, and will be given constraints based on their role. The piece’s creative direction will be guided by a local San Francisco artist. We will livestream the art-making process and add a digital layer to the recording that comments on the state of privacy on Wikipedia.