The story of Monty is about little Yorkie, who lives a very pampered life, and always carried around by his owner in a designer handbag. But the day that Monty meets Leo, the handsome and rugged Rhodesian Ridgeback, Monty begins to see how small he really is and doesn't like it one bit! He tries to rebel by walking on a leash, but it only brings confusion to his owner Melanie.

Feeling defeated, Monty talks about his small dog troubles over with his canine friends at the doggie day spa, until a Great Dane named Pito helps Monty in his ambition to be tall.