Unlike the inhabitable New York City skyline, the structural silhouettes of commercial billboards populate the city’s horizon, indifferent to any use other than transmitting paid advertisements. We propose to enlist these structural resources for community improvement and to seed landscapes in the sky. Billboards are designed as monological messages aimed at a target audience zipping past in cars in a defined direction, such as a one way street. As the flip sides of the billboards are not designed to market to a pedestrian, community scaled audience, we propose to exploit them to provide community gardens in the sky, a place for nature to take root and provide relief to the community. Our proposal encourages dialogue with the local residents without interfering with the target, drive-by audience at the same time that it greens the city. These gardens work to offset the carbon footprint of the passing vehicles. We consider it akin to planting an urban tree, only that these gardens will allow for a diversity of planting that can be tailored to local fauna and climate. Designed around self-sustaining technologies with photovoltaic panels powering the automated drip irrigation system fed from the base of the billboard towers, the gardens will require limited management once established and can be monitored in clusters from a centralized location via wireless technology.