Unlike his boss Margaret, John is very fun-loving, vivacious, and childish, playing with a road-side monkey and imagining himself having all sorts of fun. But due to working for Margaret, he is quite miserable as he never gets to enjoy what he wants to do and instead has to give into her commands. At the end of the segment, he is overjoyed and ecstatic, so he dances with some showgirls during Duke's Jazz debut.
John first appears leaving an upper-class apartment building with his wife, Killjoy Margaret, and their dog, Foo-Foo. He plays on a hopscotch game set up on the sidewalk but stops when Margaret glares at him.
Later, they pass an organ grinder with a monkey. John stops and plays with the monkey by copying his movements and dancing with him. Margaret angrily pulls him away and he reluctantly follows her into the pet shop, Le Pampered Pooch. Inside, John balances a toy bone on his nose but is soon laden down with all of the items that Margaret picks out for Foo-Foo. He goes over to the window and stares outside, wishing he could be free to do whatever he wanted. He is soon pulled out of his happy daydream when the pet store employee gives him the bill.
Towards the end of the segment, John is forced to carry all of Margaret's purchases as they walk home. After Margaret is scooped up by the hook in the construction yard, John briefly wonders where she went before seeing a poster promoting a talent night at a jazz club.
At the end of the segment, John is shown happily dancing in a chorus line with some girls in the jazz club's talent night.