Ben Singer is a failed children's folk singer, a career proofreader, a less-than-extraordinary weekend dad, and perhaps the most negative man alive. Floundering in all aspects of his life, Ben's only comfort comes from regular chess games and friendly debates on game theory with his Senegalese roommate Ibou. When Ibou is suddenly struck ill, Ben's pessimistic worldview seems unequivocally confirmed. It takes an extended visit from Ibou's sister Khadi for Ben to realize that cynicism may be all a matter of perspective.

Rainbow Randolph, popolare star TV di un programma per bambini, viene licenziato perché coinvolto in uno scandalo e sostituito dal personaggio Smoochy, un rinoceronte rosa. Quando Rainbow scopre che Smoochy ha una relazione con la sua ex amante Nora, scatta il piano per vendicarsi.

Noel Mason's vaudevillian skills are appreciated by his younger audience, but he is not making enough money at the children's shows to pay his costs, his old car does not go very well, and he is dyslexic and unable to understand the contracts employers give him. The situation starts to look more hopeful when Noel answers a newspaper advertisement to join an entertainment agency.

Nikki Brown Clown is a clown with a purpose. She advocates for Portland's displaced black community and addresses racism "in a different kind of way."