The future weighs heavily in advertising, especially when such advertisements attempt to sell catastrophe. For all the sunshine and roses that can be bought, there is still that doom and gloom to be sold. This analytical essay is an historical survey focusing on Allstate Insurance advertisements from the 1930s to early 2000s to examine the call-and-response relationship between advertising and modern society. The study looks mainly at strategies developed through print media advertisements and the various rhetorical ploys, from helping hand salesmanship to “scare copy” to brand personalities, used to sell the idea of insurance to an ever-emerging commercial public. Insurance as a business concept started off as an investment risk of its own, only to succeed as a profitable business model that became not so much an investment for many, but rather, a dependence.