Will's friend Keith is in Los Angeles from Philadelphia, looking to break into the stand-up comedy scene. Thinking that it's an easy thing to start, Will decides to go down that career path as well, despite the warnings from both Keith and Uncle Phil. When Will sneaks out of the house to go with Carlton, Hilary, and Keith to an open mic night, he gets heckled off the stage while Keith gets a standing ovation. It's at that moment he realizes it's tough to get started down a certain career path if you don't have the talent and experience.

Vivian's family is in town for a visit, upon Vy's arrival, she tells everyone that she and Robert broke up, surprising everyone. However, her announcement of Will moving back to Philly after graduating high school throws everyone for a bigger loop. As a result, Will tries to find a way to tell his mom that he would rather stay in California than move back home without making her mad.

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.

Looking to spend some quality time with Will and Carlton before they head off to college, Uncle Phil decides to take them on a camping trip. However, things go wrong when they get caught in a snow storm that causes them to take shelter in an old, abandoned cave. Meanwhile at home, Hilary tries to have a romantic evening with Trevor, only to have it interrupted by Jazz.