Grandmama Bear is Baby Bear and Curly Bear's grandmother. She lives far away in the woods, and only visits occasionally. When she visits Baby Bear in a 2000 episode of Sesame Street, it's been a few years since she's seen him, and she still thinks of him as her "little Baby Boo-Boo". She insists on treating Baby Bear like an infant -- feeding him with a spoon, burping him, dressing him in a bonnet and playing peek-a-boo.
Baby Bear confronts her, and convinces her that he's not a little baby anymore. Finally seeing her grandson as the big boy that he's become, Grandmama Bear takes him bowling.
In a Season 39 episode, Grandmama Bear was supposed to babysit Baby Bear and Curly Bear while their parents go out for the night, however she falls ill, and Gabi babysits the two bear children. Baby Bear is nervous about having a new babysitter, considering Gabi doesn't know how to do all of the things Grandmama Bear usually does while babysitting.