Weinstein began using the image of the cocktail umbrella in 2004. He was in Kathmandu, Nepal, working on a series of sculptures for an exhibition at the Pinakothek der Moderne in Munich. He had brought a package of them with him, thinking that they could somehow be transformed into a sculpture. He became interested in the local Thangka painters. He commissioned one hundred bronze parasols and then worked with the local painters to reproduce the patterns from the paper ones on to the bronze ones. The piece was not finished in time so one hundred of these illusionistic parasols arrived in his studio. Weinstein began to make patterns with them by sticking them into the wall. He bagan to arrange them in loose rectangles, following the logic of painting composition. He asked a computer programmer to make a program to create infinite combinations of them. If there are 25 of each type, and you want the greatest possible spread between each type, and you want them to form a loose rectangular grid, what will these combinations look like?
It turned out that they all looked like convinving compositions that could have been thought up by a human being. Randomly selecting one for the template, Weinstein then created his first parasol piece, One Hundred Chances For Happiness. Like the frisbee, which Weinstein used in Ed Headrick and Triumph Of Painting, the cocktail parasol is a symbol of American aspiration; not towards the future (frisbee) but to a fantasy about the good life. Working in Kathmandu, the parasol was also an acknowledgement that Weinstein was himself indulging himself in exoticism. Weinstein began painting the parasols and they became a recurring theme in his work. They appear in animated form in his animated film, Bolero, 2012.