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- Young Dylan's grandmother decides to send him to live indefinitely with her affluent son's family. The Wilson family household is soon turned upside-down as lifestyles clash between the aspiring hip-hop star and his strait-laced cousins.
- Parker J. Cloud, a former raincloud, his friend Angus, and pet walrus Russell deliver mail all across Mount Middlemost.
- 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.
- Not wanting to attend school, Dylan does whatever it takes to avoid going--including convincing little Charlie to not go either; Rebecca gets caught wearing makeup.
- 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.
- 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.
- 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 Myles to read his diary to find out if he's doing OK. Dylan catches him in the act, triggering an escalating run of family members invading one another's 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.
- While delivering a letter to a house that never gets mail, the gang goes through warfare to get to its front door. Parker does the chores in an attempt to be more like Angus and comes to realize that they're actually boring.
- 2021–202222mTV-Y78.6 (39)TV EpisodeWhen Angus accidentally throws Burt away, he and Parker must get him back from Greenwood's Recycle King. After Angus tells Parker and Russell to leave the house on his day off, Parker wrongly assumes it's permanent.
- 2021–202222mTV-Y78.5 (35)TV EpisodeAngus agrees to compete against Mayor Peeve's new POSTBOT in a mail-off to save the Middlemost Post. Parker's anxiety escalates when the cloud appears to be the source of loud nightly thundering plaguing the town.
- 2021–2022TV-Y78.2 (36)TV EpisodeAfter one of Lily's inventions goes haywire, she enlists Parker's help to get it back under control. Angus loses his lucky beanie, which causes him to revert back to being a child.
- 2021–2022TV-Y78.7 (35)TV EpisodeParker accidentally loses one of Russell's teeth and hurries to find a replacement before Angus finds out. On Free Toast Day at the Middlemost Toast, Parker does whatever it takes to make sure Angus enjoys the holiday.
- Parker's new friend turns out to be a Leprechaun in pursuit of the gold at the end of Parker's rainbow. When Parker finds mysterious love letters written by Angus, the little nimbus goes all over town to find who they're meant for.
- Parker makes snowcones for everybody in town and learns that saying 'no' isn't always a bad thing. Parker and Angus make a delivery to a spooky old woman in the Middlemost Forest - who might be a witch.
- Parker has a sleepover for the first time and enlists Angus's help to make it as fun as possible. Parker and Angus go the distance to try and give Russell a bath before her stench becomes destructive.
- Angus tries to woo the only dog on the mountain that doesn't like him: Jelly. Parker becomes overly obsessed with a game to the point where the little nimbus isn't a cloud anymore.
- Parker makes some bougie new friends while the Middlemost Post is on vacation. Angus and Parker compete in a toast-making contest hosted by Ms. Pam and The Middlemost Toast.
- When a hot air balloonist crash lands into the Steadfast, the Middlemost Post goes on a journey to help her fix it. When Parker gives shelter to a spider during a blizzard on the mountain, the cloud learns of Angus's deathly spider fear and tries to rid him of it.
- 2021–2022TV-Y78.7 (32)TV EpisodeAfter delivering mail in Purpleton, the gang finds a Baby Reggie stowaway that Parker insists on returning home. When a famous Rapper visits the Mountain, Parker gives him a new zest for life.
- After receiving the Middlemost Post's "Cloud of the Month" award, Parker gets a big head about the new title. After clogging the bathtub, Parker calls a plumber-that winds up being Ryan in disguise-to fix the problem.
- 2021–2022TV-Y78.5 (32)TV EpisodeOn Halloween, the Middlemost Post crew tell each other scary stories to get through a blackout on the ship. Mayor Peeve and the Middlemost Post compete with rival pumpkins in an annual pumpkin pageant.
- Parker learns that the mail Drone the cloud accidentally destroyed has come back for revenge. Parker, Lily, and Mayor Peeve team up to stop the zombie mail Drone once and for all.
- Parker tries to cheer up the grouchiest woman on Mt. Middlemost, Dolores Moody. Parker, Angus, and Russell must save the S.S. Steadfast from a pirate hijacking.
- 2021–2022TV-Y78.6 (30)TV EpisodeParker must save Angus from rapidly aging inside Russell's belly. Parker and Lily go on a quest through Old Stinkhole to rescue Angus.
- When Santa gets injured during a stop on Mt. Middlemost, Parker, Angus, and Russell help finish his deliveries.
- 2021–2022TV-Y79.0 (33)TV EpisodeParker finds a body hair, and the cloud assumes it's time to become an adult. During a trip to the dentist, Parker remembers how the S.S. Steadfast got shipwrecked on Mt. Middlemost.
- 2021–2022TV-Y78.9 (33)TV EpisodeParker becomes obsessed with ranch dressing. When a malevolent Smog Cloud terrorizes Mt. Middlemost, it's up to Parker to stop it.
- After Dylan goes back to his mom, he realizes that he would rather go back to his uncle Myles' house.
- 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.
- The Wilson children all turn on each other when Myles's antique vase ends up chipped.
- Myles and Dylan attempt to help Charlie get his first aid scout badge when the exercise turns into a real emergency.
- Dylan and Myles find themselves with an opportunity to bond while attending an all-night event.
- Dylan, Charlie and Rebecca come up with a scheme to make some quick money.
- Dylan and Rebecca buy a motorized scooter together but Myles and Yasmine are not happy about it.
- Dylan enters a rap contest but is unhappy when Rebecca enters his spotlight.
- Charlie attempts to "fit in" when he accidentally gains the attention of a mischievous group of kids at school.
- When Dylan and Rebecca can't seem to get along, they end up on punishment and Viola comes in to enforce it.
- While working on an after-school project, a ghost tale has Dylan and Charlie doing double takes.
- Dylan cannot seem to commit to anything as Myles realizes his gift really is music.