The most expensive/valuable Beanie Baby by far is a first-edition Princess Diana Beanie Baby. There are several on eBay, many listed in the six-figure range. The highest one is going for $350,000.
This one is a bargain at $100,000 cheaper.
If you have one of these tie-dye ones, you can sell it for about a year's salary.
Another hot item — the Valentino Beanie Baby, but it's worth the most if its tags are MISSPELLED.
Surprisingly, the prototypes — the very earliest Beanie Babies, which did not come with certain tags — are rare but not worth quite as much. They seem to sell in the $5,000 range.
Here's a "super rare" model going for $5,000.
If, for some reason, the tag is in Korean, that's good for you.
And even a few first-generation models (so long as they have their tags) can fetch a couple grand. Here's the Orange Digger going for $2,500.