With the enormous popularity of satellite and aerial photos being shown in Google Earth and other mapping tools, people who had rooftop ads suddenly realized many more impressions per day than they originally intended. I just discovered there’s a company in Germany which is selling services to make advertisements out of crop fields. Look at these amazing crop field ads (web site in German).
Just a few months ago, roof top ads suddenly got a lot of attention when people started spotting them in Google Maps and Google Earth. For example, Target has a few stores with their distinctive target-symbol logo painted 
on their large roofs. They did this when the roof can be clearly viewed by nearby skyscrapers or planes about to land at an airport. They have been pleasantly surprised with the much larger ad impressions they are getting.
Over the last few months, companies selling services to do roof-top advertising have been getting more attention and some new ones have been started to focus on the larger market of available viewers on roofs. Here’s some articles from MIT Advertising Lab and Wired on rooftop ad companies for new investments.
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The big drawback to doing this is that there is no set schedule for when new satellite photos of roofs and fields will be done. So, you could put up an ad tomorrow, but it might not be seen by a satellite or aerial photographer for months or years. And, it might be even longer before Google chooses that photo and puts it up in their database. So, expect your sky-viewable ad to be a long-term investment.
About Frank Taylor
Frank Taylor started the Google Earth Blog in July, 2005 shortly after Google Earth was first released. He has worked with 3D computer graphics and VR for many years and was very impressed with this exciting product. Frank completed a 5.5 year circumnavigation of the earth by sailboat in June 2015 which you can read about at Tahina Expedition, and is a licensed pilot, backpacker, diver, and photographer.
A much faster and even cooler way to accomplish the same effect is to have a structure modeled in 3D. That way if a company does have a sweet new rooftop ad, it can be immediately placed on Google Earth with the model.
Stray Kat Studio (based in Alaska) does high quality model work, and can create a model anywhere in the world, as long as someone can email the photos.