Martha Stewart, the most famous homemaker in America, started as a model and eventually ended up in jail.

In late 2001, Martha Stewart was informed by her broker that the CEO of Imclone was selling all of his stock. She sold all of her shares, almost 4000, and the following trading day the stock dropped 16%.

The insider trading investigation became a huge news scandal because of how contrary it was to her image. She served her time and is now back, better than ever (including with a show she did with Snoop Dog).