Dylan gets ready to return to Chicago with his mother when a change in the plan causes him to question their relationship and prompts the Wilson family to help him through this latest crisis.
Charlie seeks Dylan's help when he has a crush on a girl, but Dylan's rap music-informed advice clashes with Rebecca's more feminist take on how Charlie should handle the situation.
When the school does a hip-hop version of Shakespeare, Dylan takes on another boy for the lead role; after only being cast as an understudy, Dylan is determined to outshine his rival and nab the part for himself.
A lucky guess in math class lands Dylan on the Mathlete squad, where his teammate, Rebecca, is worried that he will hurt their chances in the upcoming regional competition.
Dylan plays detective after an expensive vase is broken in the house, but no one admits guilt, and everyone is a suspect.
Dylan has a new track that he's sure will get some attention, but he needs a female vocalist for the hook and after using Rebecca for the part, he can't contain his jealousy when she starts getting more attention than him.
Myles joins Dylan in camping out overnight for a chance to appear in a music video and score new sneakers, but a series of mishaps threatens Dylan's ability to actually get the shoes.
When a valuable collectible that Rebecca and Charlie sneak into school is confiscated by the principal, Dylan must help his cousins pull off an elaborate heist to retrieve it before Myles realizes it's missing.
Rebecca wants to use her new scooter to make social media posts, and Dylan wants to use it in a rap video, but both need to hide it from their parents if they want to keep it.
Accidentally trapped in the garage with Myles, Dylan puts his street smarts to the test against Charlie's scout smarts to see who can find a way out.
Charlie is tempted to change his clean reputation when a group of school vandals invites him into their clique, forcing Dylan to try to change Charlie's mind; Rebecca and Bethany protest when they are not allowed on the football team.
Rebecca and Dylan, desperate to sneak out of the house, plot how to get past Viola, nicknamed "Alcatraz" because no one has ever escaped on her watch; Charlie prepares a report on a historical person who inspires him.
Dylan insists that baseball isn't another one of his fleeting interests, but when he decides he wants to quit after a few days, he has to hide it from the family; Rebecca struggles to choose something for her class time capsule.
Dylan and Charlie decorate the school for a Halloween party and discover that the creepy janitor might be keeping a spooky secret; Rebecca and Bethany can't agree on a two-person costume for trick-or-treating.
Dylan's popularity skyrockets when he engages in an online rap battle, but the pressure to settle the beef at school creates a new set of problems; Rebecca's upcoming solo at church spurs Yasmine and Viola to offer fashion advice.
Rebecca's assignment to study animals in the wild leads her to observe Dylan and Charlie as they battle for suprema
Blamed for a classmate's prank, Dylan must decide whether to reveal the real culprit, or suffer the consequences for taking the fall; Charlie and Rebecca think the family is being evicted from their home.
Hoping to be a baller in his latest music video, Dylan secures a credit card and starts ordering everything he needs to look the part, but after getting Rebecca and Charlie on board, the kids learn that credit card debt has to be paid back.
The family tries to make Dylan's first Christmas away from home special, but goes overboard trying to recreate his favorite traditions; the kids panic when they realize they don't have gifts for their parents.
Dylan discovers his new substitute teacher is a former rap star, and Dylan plots to get him back on top; after successfully reviving the former star's profile, Dylan finds that own dream remains out of reach.