5. BINGO IN BINGO (1991)

Over the course of one movie, Bingo lives the life of 20 canines. Starting the film off as a circus dog, Bingo evades his owner’s shotgun and then sparks a friendship with a bullied kid, with whom the little pooch plays pinball and, yes, skateboards. The kid’s parents aren’t having it, though, so Bingo is sent packing, leading to a road trip in which the hairy protagonist goes to jail and earns the respect of hardened inmates. Just don’t sing that goofy “B-I-N-G-O” tune 'cause he’ll take it back to the yard in a flash.