Hillary's boyfriend Trevor uses an old contact to pull some strings to get Phillip and the family on Oprah's show to talk about family and politics. Will's thrilled about going to Chicago and being on television with them, but there's one small detail, it's only the immediate family appearing on the show. When Will finds out, right before they go on stage, he's mad and jealous about having to sit in the audience. As a result, when Oprah calls on the audience for questions, Will starts embarrassing the family on national television.