The Simpsons (1989)

S9E18 This Little Wiggy

Marge encourages Bart to have a "play date" with Ralph, and at first, Bart is reluctant. However, his perspective shifts when he stumbles upon Chief Wiggum's "master key." Excited by the discovery, Bart decides to use it to venture into the abandoned prison in Springfield, revealing the hidden adventures that come with this unlikely friendship.