I've come to find out that this bear is apparently a Knickerbocker bear.
While that helps alittle, I am still unable to find out anymore information
on the bear itself (i.e. why it was made with a plastic face and why it
looks so sad) Any suggestions?

Examples of the bear I speak of:

http://cgi.ebay.com/ws/eBayISAPI.dll...tegory=11 7&r
d=1

http://cgi.ebay.com/ws/eBayISAPI.dll...tegory=31 &rd
=1