Young Dylan arrives at his relatives' home needing a place to live, but his streetwise swagger upends the conservative Wilson household.
Yasmine’s celebrity client DJ Khaled visits, presenting Dylan with a golden opportunity to prove his rap credentials and score a record deal.
Dylan has trouble adjusting to the Wilson family’s rules, leading to confrontation with his uncle that makes him feel unwanted.
Dylan doesn’t want to attend school, and does whatever it takes to avoid going, including convincing little Charlie not to go, either.
On his first day at school, Dylan starts a classroom protest over having to wear uniforms.
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.
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.
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 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.
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.
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.
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.
The family can’t get any peace while Dylan plays the drums all day and night, and each tries to convince him that he needs to give up his new instrument for good.
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.
Dylan gets ready to return to Chicago with his mother, but a change in plans has him questioning their relationship, and the rest of the family trying to help Dylan 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.
With the school doing a hip-hop version of Shakespeare, Dylan takes on another boy for the lead role. But 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 teammate Rebecca is worried that he will hurt their chances in the upcoming regional competition.
Dylan begins to play detective after an expensive vase is broken in the house, where no one is admitting 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. 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 her 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.
Desperate to sneak out of the house, Rebecca and Dylan plot how to get past Viola, who is 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 the decision from the family. Rebecca struggles to choose something for her class time capsule.
While decorating the school for a Halloween party, Dylan and Charlie 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 (and sometimes provoke) Dylan and Charlie as they battle for supremacy in their small shared bedroom.
Blamed for 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. Meanwhile, the kids panic when they realize they don’t have gifts for their parents.
Dylan discovers that his substitute teacher is a former rap star and plots to get him back on top. But after reviving the former star’s profile, Dylan finds that own dream remains out of reach. Will he quit the game for good?
With the annual Juneteenth parade on the horizon, Dylan and Rebecca find themselves at odds over the float parade. Elsewhere, Myles and Yasmine utilize Charlie’s culinary skills to bake pies for Viola’s church social.
When Dylan and Lay Lay get duped into buying fake designer clothing, they team up to track down the scammer. Charlie and Rebecca misplace a valuable watch while spring cleaning with Myles and Yasmine.
Dylan becomes an egomaniac when he thinks his latest song is a #1 hit in Nigeria. Yasmine enlists Rebecca to direct a commercial for her business.
Faking sick from school, Dylan and Charlie plan a day of fun with Rebecca hot on their tail to expose their lie.
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.
Appointed hall monitor, Dylan finds the job more than he bargained for. With their parents working evenings, Rebecca and Charlie must prove they can hold down household responsibilities by themselves.
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 falling asleep in class due to staying up late for a family tradition with Myles, Dylan is forced into Saturday detention. The family deals with Viola’s competitive nature on game day.
After Myles and Yasmine enforce a “no technology” policy into place, Dylan, Rebecca and Charlie find themselves on a treasure hunt in order to retrieve their gadgets.
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.
Tasked with writing a history report, Dylan travels back in time to the Harlem Renaissance.
Dylan tries to create drama between his family and friends for his reality show audition tape.
Dylan and his new friend Tara plot to sabotage Bethany and her date to the school dance. Charlie is put in charge of the Mardi Gras themed dance.
Rebecca puts a curse on Dylan. Charlie orchestrates both dinner and the perfect gift for his parents anniversary.
Dylan comes face to face with "Dylon" – not only a second-rate version of himself but Bethany's new crush. B Story: Myles tries to help Yasmine fix the home patio.
Dylan and Rebecca learn that honesty is the best policy after finding a valuable item tossed in the trash. Booder showcases his magician's skills and tricks Dylan and Rebecca into being his assistants.
When the family vacation entails an unwanted camping trip, Dylan and Rebecca devise a plan to sabotage.
Charlie enlists Dylan to help run his campaign for school ambassador against their mutual enemy Ace.
While receiving tutoring from Bethany, Dylan's decision to cheat leads to sabotaging Bethany's class presentation.
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It's Halloween, and the Wilsons take the holiday very seriously; Dylan must deal with his family dressed up for Halloween when the heads of a hot brand stop by to interview him as a potential spokesperson, but while trying to do so, he experiences a series of fright, horror and trauma.
Dylan tries to mend a rift between Rebecca and Bethany only to make matters worse.
Dylan tries to convince local street artists to create a mural featuring himself resulting in widespread chaos.
Dylan and Rebecca hatch up a plan to set Viola up on a date with the delivery man.
After Rebecca is chosen as a model for a hot clothing boutique, Dylan and Bethany will do anything to get her back.
Deciding they aren't babies any more, Dylan and Charlie start turn their bedroom into a man cave.
When Rebecca embarks on a mission to sell Fun Goo, Dylan accidentally ruins all of her products, causing sabotage to her master plan.
« Previous Ep. Next Ep. » Dylan and Charlie's holiday spirit comes to a halt when they are trapped in a delivery van on Christmas eve.
In an epic sleepover showdown, the girls and boys engage in a fierce battle to claim dominance over the living room.
After Charlie's video of Dylan performing a dance goes viral, Dylan must recover his reputation at school.
When Dylan accidentally signs up for a gift-wrapping competition instead of a rap battle, he must rely on his cousin Rebecca's training and his own rhythmic skills to wrap his way to victory and avoid a year of chores.
