It may come as a surprise to the admirers of chrome-coated fenders and the “potato potato” voice of V-twin motors that the actual task of selling a Harley-Davidson isn’t as easy as it looks. The Milwaukee-based brand plays in the premium category—a 2012 Road King Classic in all its spaghetti-piped splendor lists for $19,599—and that becomes a hard sell when the economy goes soft. (Harley survived the Great Depression by selling its bikes to police departments.) But a bigger challenge lay not with the bike or its price, but the ever-changing image of the rider. As the ads here show, the ability to shift gears quickly can apply to the marketing just as much as the motorcycle.