I've written about Buckley's Cough Syrup before. For the past 15 years, it's a brand that has built itself on its horrible taste. The idea is, if it tastes this bad, it has to work. And it's a great story.
The strategy is dead on. Not only does it take a negative product trait and give it a positive spin, but it targets a specific audience: people who want to get better at any cost. You either love Buckley's or you hate it. There's not a lot of middle ground. And that's a good place for a brand to live.
From the article: "It's a medical product, and medicine isn't supposed to taste like an orange drink. It's supposed to taste bad to kill the nasty virus in the back of your throat."
Read the whole thing.