Bear, real name Littlefoot, is a toy from Lewis's past, whom he seems to take most places. Bear is mostly used for comedy, but in a previously on segment, Bear was shown to be masterminding an evil plot, showing us that there might be more to Bear than what meets the eye.
In Kickassia, Linkara made multiple attempts to use Bear as part of a makeshift grappling hook.
In a Silent Hill alternate ending, Linkara wanders into a Star-Trek looking room, proclaiming "It was you all along...Bear!" A chair swivels around to reveal Bear sitting in the middle of it.
Later on, Linkara is shown asking Bear if he's ready for his picnic, and can be seen holding a picnic basket. When Linkara looks back, Bear has vanished. Linkara wonders how he can do this, though doesn't seem overly concerned and has not brought it up since.