Dylan writes a serious rap about his mom, prompting Martin to read his diary to find out if he’s doing ok. Dylan catches him in the act, triggering an escalating run of each family member invading the others’ privacy.

On his first day at school, Dylan starts a classroom protest over having to wear uniforms.

When Lay Lay and Dylan get duped into buying fake designer clothing, they team up to track down the scammer.

Rebecca is being bullied online, prompting Dylan to encourage Martin to respond to some of the posts. His posts are not anonymous, however, and the family must deal with the fallout.

The kids help Myles plan Yasmine’s big dinner at the house for her boss. While Myles struggles to write a speech in honor of his wife, the kids throw out the catered food and plan their own menu.

Yasmine’s celebrity client DJ Khaled visits, presenting Dylan with a golden opportunity to prove his rap credentials and score a record deal.

Dylan becomes an egomaniac when he thinks his latest song is a number one hit in Nigeria; Yasmine enlists Rebecca to direct a commercial for her business.

With the annual Juneteenth parade on the horizon, Dylan and Rebecca find themselves at odds over the float parade; Myles and Yasmine utilize Charlie's culinary skills to bake pies for Viola's church social.

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.

After failing to get approval to go to the school dance, Rebecca tells her date that she can’t go because her grandmother has died, a lie that leads to a series of misunderstandings within the family.

Dylan doesn’t want to attend school, and does whatever it takes to avoid going, including convincing little Charlie not to go, either.

The family can't get any peace while Dylan plays the drums all day and night, and everyone tries to convince him that he needs to give up his new instrument for good.

Rebecca is babysitting Charlie and Dylan, but when a deliveryman arrives with a package from Dylan’s mom, Rebecca and Dylan fight over the rule about not opening the door.

Young Dylan arrives at his relatives' home needing a place to live, but his streetwise swagger upends the conservative Wilson household.

Dylan has trouble adjusting to the Wilson family’s rules, leading to confrontation with his uncle that makes him feel unwanted.

Dylan tries to help Charlie with his homework, but his unconventional style of doing his homework comes to a head with Dylan gets into a rap battle with their teacher.

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.

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.

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.

Dylan has a dream about his mom returning to get him, and reveals that he doesn’t want to leave. This becomes a reality when Viola reveals that Dylan’s mom is back, and planning to take Dylan home with her.

The day of Dylan and Rebecca's launch party for their label is finally here! However, after a venue Rebecca had planned ends up being taken, the duo must find a way to secure a new venue for their big event before it's too late; Charlie and Viola contribute on their part to the label by opening up a mini diner at the house.

After Charlie's video of Dylan performing a dance goes viral, Dylan must recover his reputation at school; Myles and Yasmine use coupons to trick Rebecca into doing house chores, until Viola and Rebecca get the upper hand.

When Dylan is assigned to write a history report for school, he travels back in time to the Harlem Renaissance.

Charlie's habit of listening to other people's private conversations goes wrong after he informs Yasmine and Miles of Dylan's new life plan; Rebecca learns the meaning for true friendship and accepting oneself.

Dylan plays detective after an expensive vase is broken in the house, but no one admits guilt, and everyone is a suspect.

Rebecca's assignment to study animals in the wild leads her to observe Dylan and Charlie as they battle for suprema

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.

After secretly opening his birthday gift from Myles and Yasmine early, Dylan must invent a cover up when he accidentally destroys it; the family plans to be the top seller at the neighborhood yard sale by way of Charlie's culinary skills.

Dylan and Rebecca form an unlikely team to win a school gaming competition; Charlie is tasked with painting a portrait of Myles and Yasmine.

After his old rap group from Chicago pays him a visit, Dylan must decide between the past and his future as a solo artist; Rebecca puts Myles and Yasmine on a strict diet regimen.

Dylan and Charlie cause chaos among the family in an attempt to create a dramatic audition tape for a reality TV show; Rebecca and Bethany teach Dylan a lesson about compromising his values.

As the school dance approaches, Dylan and Tara work together after they realize they have the same nefarious hidden agenda; Yasmine becomes overly protective of Charlie when the family supports his decorating efforts.

Viola and Dylan work on his de-stressing skills so that he can reconnect with his rapping abilities; Yasmine reluctantly seeks help from Charlie for her anniversary plans.

Rebecca offers anonymous advice to her peers and a superior but goes further than is appropriate; Myles and Yasmine struggle to be partners until Charlie leads them with his advice.

Dylan must make amends after he invades the privacy and violates the trust of a classmate; Yasmine and Myles are disappointed when Charlie uncovers an awful truth.

Charlie gets his first job but must stand up for himself in order to keep it; Rebecca realizes that Tracee may be more manipulative than she appears.

When he's hired to perform his hit viral song for a commercial, Dylan's artistic integrity is tested; Charlie must give a school presentation on someone in his family tree.

Dylan and Charlie's holiday spirit comes to a halt when they are grounded and are trapped in a delivery van on Christmas Eve; Yasmine becomes the student after trying to teach Rebecca a lesson about gratitude.

As Myles and Yasmine sort out the truth behind a lie that spun out control, Dylan helps them plan payback on Rebecca before she gets home.

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.