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Bertram’s new toupee that he bought for his band’s big performance has gone missing, so Jessie interrogates each of the kids in hopes to find it.
It’s school dance time, and the Ross family pulls out all of the stops to score dates. Meanwhile, Jessie helps Bertram prepare for his first solo at the Metropolitan Opera.
In the final part of the “Rossed at Sea” three-parter, Jessie abruptly ends the Ross family vacation because the kids are constantly fighting. They wind up in a pickle when they find the yacht the next morning floating in the middle of the sea with no captain or crew in sight.
While exploring an Italian island, the Ross family’s tour guide tells a story about Jessie’s necklace, and how its curse brings anyone who wears it bad luck in love.
While on vacation, the Ross family finds a girl stranded in the middle of the ocean and invites her aboard their yacht. Meanwhile, Bertram stays home and babysits Mrs. Kipling, who has separation anxiety from Ravi.
Bertram has had enough, so decides to quit and to go work for Mrs. Chesterfield. Meanwhile, the Ross family hires a new butler, Roger, who takes his job very seriously.
Emma wants her license, so Jessie teaches her how to drive. Ravi and Luke accidentally break one of Zuri’s games, forcing a stand-off.
In an effort to help Ravi make friends, Jessie takes him to a MENSA meeting in the park. However, their new friends, Madeline and Scott, may be too good to be true.
When the kids are snowed in at the penthouse, an epic game of capture the flag ensues. Allegiances are tested, tricks are pulled and everyone goes a little overboard.
Eager to play in Luke’s basketball game, Ravi unexpectedly runs into LA Clippers star Chris Paul, who he enlists to coach him. Meanwhile, Jessie learns that Hudson is her new classmate and is unhappily forced to partner with him for an assignment.
Jessie finds herself in unfamiliar territory when Emma’s unexpected behavior gets her into trouble at school. Meanwhile, Luke takes on the role of Sensei to train Zuri for her upcoming karate belt test.
Jessie goes back to college and ends up in the same class as Ravi. Meanwhile, Zuri brings home a baby giraffe from Africa.
The Ross family faces an unexpected dilemma when they find out their parents have lost all their money and must learn to live without it.
Jessie’s stepsister Darla comes to visit, and Jessie enlists Tony’s help to try to cover up the fact she didn’t go through with the wedding. Meanwhile, Luke shaves for the first time and when Bertram comes to help, things get a bit hairy.
In the season four premiere, the Ross kids are convinced Jessie is headed to Africa to rekindle her relationship with ex-fiancé, Brooks. In an effort to stop her, the kids make the trip to Africa and quickly find themselves on a wild adventure.
Parker and Joey, Jessie and the Ross kids plan a tropical Christmas at the family’s Hawaiian villa where Jessie reunites with old friend and superstar, Shayelee Michaels.
Jessie is on a mission to get to an important audition; however, she and Ravi wind up on the “Rides to Riches” game show in which contestants can win prizes during their taxi ride.
Jessie and the Ross kids plan a tropical Christmas at the family’s Hawaiian villa where Jessie reunites with old friend and superstar, Shayelee Michaels.
The Halloween Festival takes a scary turn when Brooks proposes to Jessie and she learns that none of the Ross kids approve.
Unhappy with her son’s budding relationship, Mrs. Chesterfield hires Bertram; she’s hoping he finds dirt that will cause Brooks to break up with Jessie.
Jessie hits it off with a new guy she meets in the park named Brooks, unaware that he is Ms. Chesterfield’s son.
When Jessie lands two VIP wristbands to Emma and Zuri’s dream concert, the girls compete to be her guest. Meanwhile, Bertram becomes infatuated with his new talking coffee maker.
Jessie agrees to accompany Bertram to his high school reunion, so he can show his former classmates how successful he has become.
Ravi’s birthday present from his parents is a trip to outer space with the rest of the Ross kids and Jessie. Their trip takes an unexpected turn when Ravi ends up not going.
Jessie becomes frustrated that she can’t land any acting gigs, so she takes matters into her own hands by participating in a 24-hour film festival. She recruits the kids to help her direct, shoot and edit her film, but things get complicated when all the kids have their own ideas about what the film should be.
Jessie races to make sure the Ross kids make it to school on time, but there are many bumps along the way.
Jessie and Zuri discover Stewart has a new laid-back “manny” named Hudson. Having grown to like Stewart, Zuri resents being told not to see him, and they run off together.
Jessie is in need of some extra money to buy a special gift for her dad’s birthday. She accepts a job at Empire Skate Building only to find out that Emma is her boss.
Jessie and Zuri set out to host a birthday party for Taylor, a new friend who’s sorely missing her mother, a deployed member of the military. When Taylor decides she’d rather not celebrate anything without her mother, Zuri enlists the help of Mrs. Obama.
Jessie makes a friend in acting class only to find out her new pal Abbey is not all that she seems.
Creepy Connie returns with a sidekick, Mackenzie. The two play a cat and mouse game as they vie for Luke’s affection.
Jessie hooks Zuri up with a new girl named Wendy McMillan after seeing a director to get her acting career started. With Jessie she’s an angel, but while Bertram is in charge, she tears up the place and wrecks everything. Bertram tries to take care of it, but Wendy hooks Bertram up too. Zuri tells Jessie she’s a monster and wants to stop playing with her. Meanwhile, Emma goes over her limit on her cell phone bill, so Jessie forces her to get a job so she can pay the bill herself.
Jessie asks Emma to invite the new girl from the building to her party as a welcoming gesture.
When Teddy Duncan (Bridgit Mendler) gets accepted into a college in New York City, she goes to New York, alongside her brother P.J. (Jason Dolley), and meets up with Jessie. When a blizzard traps P.J and Teddy in New York City, Jessie and the Ross kids try to get them back to Denver the rest of the Duncan family go and get them as well. Meanwhile in Colorado, Gabe (Bradley Steven Perry) is being a scrooge.
Jessie is excited when she and the Ross kids are invited to participate in a reality show.
Luke asks his adoptive mom, Christina, for information about his family history after he is assigned a report at school.
Jessie decides that she and Tony will set each other up.
Jessie gets an opportunity to be the understudy in an off-Broadway play. Unbeknownst to her, Luke plots to sabotage the star so Jessie gets to be on stage. Meanwhile, Emma and Zuri help Bertram make a web show in which he is the star.
