Big Boss appears in Betty Boop's Big Boss. He is looking for a female secretary to work in his office. Many women attend the interview along with Betty Boop. Betty sings You'd Be Suprised, to win him over, all of the women who attended the interview are classed as ugly by Big Boss, so they are all thrown out of the office. While Betty is working for him he is deeply lusting over her, but by accident Betty knocks the type writer into him which makes him spit out his cigar, Big Boss walks over to Betty in a furious manner, Betty responds by saying "Did i hurt my Pupsy Wupsy?". Big Boss tries to kiss Betty, but she tells him that he is naughty. He then chases her and the door locks itself, so Betty runs to the phone and calls the police. The whole Army come to rescue Betty, including Bimbo who seem's to be a policeman, only to be told by Betty, who is kissing Big Boss that they are fresh.
While Betty is singing You'd Be Suprised, she flashes her underwear to Big Boss.
When the police try to shoot Big Boss with their guns, and he shoots them back, Betty says "I wanna play too" and grabs a pencil sharpner and uses it as a gun to shoot her Boss in the behind.
When the Police & Army are about to save Betty, by shooting all the building down it looks like she is being strangled, until they open the curtains to see her kissing the Boss.
Betty refers to him as being a Pupsy a name she would later use for her pet dog Pudgy, which might indicate that Big Boss is a dog.