He's occassionally paired with the show's master of ceremonies Henry, forming a comedy duo with him.
Behind the Scenes
Wendell and his songs with Henry were taken from a musical comedy duo called "Homer and Jethro", with Wendell being inspired by Jethro. Much of his banter with Henry was taken directly from the songs the Imagineers chose to use, with Henry having gained the name to better preserve those lines.
From 1972's Country Bear Jamboree record album:
Wendell is a frustrated basketball player. He quit the game when in the team photograph, he discovered he came up to the other players’ knees. He then turned to baseball, but three people stepped on him (they thought he was second base). He went from baseball to football, until two quarterbacks threw him for touchdowns. It was after his gridiron career that he latched onto Henry. When Wendell and Henry get together—well, nobody dares mistake Wendell for anything but what he is: a small, singing bear.