Jessie is an 18-year old girl from a rural Texas town who moves to New York City. She suddenly finds herself becoming the nanny of four children living in a multi-million dollar penthouse in a hotel after being pushed out of a taxi. One of the youngest children just asks her to be her nanny and now Jessie has to get them to get along by keeping them from fighting. One of the children has an imaginary friend and another has a pet water monitor lizard. Assisting her is Bertram, a mean, lazy butler and Tony, a 20-year-old doorman who secretly likes Jessie.
Jessie directs a play she's written and casts Luke as the male lead; the play is a love story, and 'Creepy Connie' is the female lead. Meanwhile, Zuri job-shadows Bertram for her school report.
Mrs. Chesterfield hires Bertram to dig up dirt on Jessie that would hopefully lead Brooks to break up with her.Watch Now:Amazon
Jessie, Bertram and the kids head to Bali for a family vacation, but when their private jet starts to experience difficulties, Jessie takes control of the cockpit and makes an emergency landing on a tropical island. Jessie must figure out how to get the kids home safely, all while recovering from poisonous bug bites, escaping scary monsters and tracking down Mr. Kipling.
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.Watch Now:Amazon
The series concludes with Christina Ross returning home and Jessie heading to Los Angeles for a role in a movie. But when the kids realize they still need Jessie, they follow her to Hollywood.
While the Ross Family has their traditional "Gotcha Day", Jessie is left in charge to help celebrate the time when Zuri was first welcomed home in New York City. When Ravi tells the story when he first arrived in the United States, he tells Jessie that they thought Mr. Kipling was supposed to be a baby because his room was decorated as a nursery. Jessie accidently blurts out that Morgan and Christina were probably expecting a baby. Ravi gets incredibly upset; Christina gets infuriated with Jessie. The huge reveal almost ruins "Gotcha Day". Later on, Morgan and Christina tells them that his birth certificate had a typo and instead of Ravi being born in the year 2001, it said 2011, so that is why the Ross' were expecting a baby. In the end, Ravi forgives Morgan and Christina, and they give Zuri a zebra as a "Gotcha Day" present.
Tony and Jessie attempt to make each other jealous by asking their exes on a double-date, causing the duo to break their dating relationships, which also saddens Emma & Zuri in the process. Meanwhile, Luke & Ravi attempt to sabotage each others' plans on how to relieve Bertram's stress level. Unfortunately, this leads Bertram into thinking that the Ross brothers don't actually care about him. Also, he's hypnotized into thinking that he's a stray tomcat.Watch Now:Amazon
Jessie lands a job as a stunt double for a popular Australian actress, but things get tricky when the movie's director and the actress's boyfriend ask Jessie out on a date. Meanwhile, Emma helps sneak Zuri's pet zebra into the penthouse.Watch Now:AmazoniTunes
When Brooks lands a job in Africa and has to be there in two days, he and Jessie are forced to move up their wedding.Watch Now:Amazon
Emma and Zuri plan a romantic mystery-filled fifth first date for Jessie and Tony. Meanwhile, Ravi, Cameron and Bertram get stuck in a giant teacup on a billboard, after their failed attempt to rescue Ravi’s toy helicopter.
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.Watch Now:AmazoniTunes
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.Watch Now:Amazon
In this one-hour special cross-over episode with "Liv and Maddie's" 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.
After the girls watch a scary movie, Jessie tries to help Zuri conquer her fear of dolls by confessing her own fear of porta-potties. Meanwhile, Cameron teaches Ravi how to impress a girl and Bertram listens to opera non-stop to win a radio contest.
Jessie races to make sure the Ross kids make it to school on time, but there are many bumps along the way.Watch Now:Amazon
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.Watch Now:Amazon