Princess The Bear

Princess the Bear was created by Ty in commemoration of the late Princess Dianna and is one of the only beanies on this list that is linked to a tragic historical event.

When Princess Diana was immortalized as 'The People's Princess' in innumerable commemorative items after her death in a car accident in August 1997, Ty Inc, the maker of Beanie Babies, launched its own commemorative item in October 1997. Two months later, a limited-edition plush dubbed 'Princess the Bear' with a purple ribbon and white rose around her neck was released in retailers. The Diana, Princess of Wales Memorial Fund received 100% of the proceeds, which was used to continue the princess' humanitarian efforts after her tragic death.

To create a sense of exclusivity, Ty Inc said that each merchant will get only 12 Princess the Bear toys. When the toy's enormous popularity became clear, the business shifted course and began mass-producing the bears in the thousands. At the time, the toys cost between $5 and $7. Because it's incredibly rare, it now normally commands a price of around $500,000.

Price: $500,000