With a global reach of over a billion persons, Internet entrepreneurs are consistently looking to adopt traditional promotional and business models to this broader audience. Business and promotional activities like sweepstakes, promotions and contests that appeal to the gambling instinct have had a sordid legal history as most U.S. states have laws that generally prohibit gambling. Not all such activities, however, are illegal. For example, retailers have long understood the value of sweepstakes to help sell products. Likewise, skill games for prizes have lined the midways of the country’s state and county fairs for decades. Both activities rely on the public’s desire to play games where they can ultimately win prizes. As long as the public has an unfulfilled demand for a gambling experience, entrepreneurs continue to test the boundaries of legal sweepstakes and contests to meet these demands. The variations of sweepstakes and contests are bound only by human imagination and unbound by tremendous leaps in technology.