As Grandpa tells stories about the Nutmeg family tree, Heathcliff falls asleep and dreams about his family tree.
The first of his ancestors is a cowboy-like tomcat The Orange Bart. He lives somewhere in the Wild West. His scene begins with him walking in a saloon, where the most of the customers are frightened of him. He orders a glass of milk. Then, he is greeted by a cat, who resembles Sonya. She seems to like him. Then, another cowboy tomcat barges in, his name is Calico Kid. He provokes Bart to a fight, stating that he has "the fastest fish" in the Wild West. They make a countdown and The Orange Bart takes off a pair of fish from where pistols should be. He beats Calico Kid up and the Sonya lookalike falls to his hands. She asks him, when is he going to "hang up his fish". He replies: "When you say that you are gonna marry me".
The second ancestor is called Heathein-Hood. He is probably a prank on Robin Hood. He is walking through a forest and singing a song about giving to the poor. He meets some dogs and cats and gives some money to them. Heathcliff soon escapes from this "branch", feeling disgusted.
The final sequence shows a colloseum filled with gladiator fight fans. There is a match going on between Herman the Hun, a tomcat, who resembles a fat alley cat from Heathcliff's present time, and Heathacus, another Heathcliff's ancestor. The crowd is cheering for Hethacus and he easily ovepowers Herman.
After Heathcliff wakes up, Iggy tells him, that he saw an alley cat chasing after Sonya in the junkyard. Heathcliff rushes there and stops the alley cat (the one, that looks like Herman). After that, he and Sonya are walking on the street and Heathcliff pushes some garbage cans, much to the anger of garbage men. Heathcliff then sings a song, which is very similar to the Heathin-Hood's one, but with lyrics, that describe Heathcliff as he is.