These are what we call the 'YMMV items.' Things that some people find in this work. We call them 'your mileage might vary' because not everyone sees these things in the same way. This starts discussions in the trope lists, a thing we don't want. Please use the discussion page if you'd like to discuss any of these items.
Alternate Character Interpretation: Are the Ross parents extremely successful celebrities who are simply too busy maintaining their financial empire so that their children can afford keeping Bertram, Jessie and all of their material possessions around and legitimately love their children, or are they irresponsible self-absorbed attention freaks who have clearly adopted far too many children just for the sake of appearances and have left them to be raised by money, resulting in four clearly spoiled brats?
Is Jessie really a Magical Nanny or dangerously incompetent and ill-suited for the job? Even the show itself has a hard time deciding, with her own kids making fun of her skills.
Also, Jessie is engaging in Obfuscating Stupidity. She can fly a helicopter and was a straight-A student in high school, after all. The fact that she genuinely can do right and give good advice is also telling.
One joke suggests Ravi cares for Kipling's children out of fear of her.
The same can be said about Ravi. His "relationship" with Mrs. Kipling is pretty annoying as is the way he treated her young. At least Zuri and Ravi both have some of the funniest scenes, but at the cost of simultaneously being two of the most annoying characters on the Disney Channel.
Also, a couple of the racial jokes in the show are rather unsettling to say the least.
Zuri's slurs against citizens of Denver and Denver itself in Good Luck Jessie.
Ear Worm: Even if you don't like the theme song, you've got to admit it's catchy.
Ensemble Darkhorse: One of the most popular characters in the whole show so far is Creepy Connie - a character who not only was meant to be as close to walking Nightmare Fuel as a series of this nature would allow, but also a character who has appeared in a whopping two episodes.
Officer Petey, who has now appeared in two episodes each season so far and certainly in future ones.
Arguably Nanny Agatha, who's appeared in as many episodes as Officer Petey has so far (including one with Officer Petey)
Fridge Brilliance: Tipton Tea from "Tempest in a Teacup" might not make much sense past Tipton Industries having owned quite a few random properties. But if you think back to the "Boston Tea Party" episode of The Suite Life of Zack and Cody, back in the 1700s, Lord Tipton owned a tea ship and was having tea shipped to America a few hundred years ago.
Fridge Logic: Jessie states in "Tempest in a Teacup" that her prom ended with her embarrassment at her Senior Prom. Prom is typically in May and she graduated in June. She arrives in New York in what appears to mid to late summer or early fall. She either left very soon after graduating and didn't get to New York City months later, or had many more of her wrecked relationships after graduating but before packing up and leaving for New York. Either way, while she didn't have the best life in Fort Hood, Tx, the Prom incident is more than likely what caused her to leave town. Going to New York is just a side bonus. And why didn't she choose Los Angeles. Make you wonder about her, not to mention What Might Have Been had Jessie gone west.
Fridge Horror: In "World Wide Web of Lies," Mrs. Ross tells Jessie that she's under 24 hour surveillance, to the point where they know of Jessie's sleep-eating (which Jessie herself doesn't even know).
"Funny Aneurysm" Moment: After "The Whining" aired, a nanny in New York did kill two of her kids like the Ross children thought Jessie wanted to do. Disney has since pulled all reruns of the episode and it was removed from iTunes.
The pulling of the "Quitting Cold Koala" episode can be considered this as it was pulled before being aired due to jokes made about Gluten-free dieters. It was to air in May of 2013 and May is National Celiac Disease Awareness Month. People with Celiac Disease cannot eat gluten.
In-universe example: In "Gotcha Day" Bertram warns Mr. Kipling that if he ever has kids Bertram will make omelets out of them. In "The Secret Life of Mr. Kipling" (which happened to be the very next episode,) Mr(s). Kipling's unhatched kids are in danger by being trapped inside a restaurant - that specializes in making omelets!
In "Girls Don't Wanna Get Shunned" Jessie warns Bertram about how nasty and backstabbing teenagers are - then Bertram points out that Jessie is a teenager. This episode aired just a few weeks before Debby Ryan's 20th birthday (and was thus no longer a teenager).
Girl-Show Ghetto: Averted by using an equal cast of three guys and three girls, giving both the male and female characters important (if not entirely equal) roles and attracting both male and female viewers with eye candy. You can take the viewpoint that the show is slightly shifted more towards girls because Jessie herself is the title character, Peyton R. List is the second actor billed & Zuri is the first regular character the audience is introduced to after Jessie.
Heartwarming In Hindsight: In one episode, Jessie delivers a speech on how precious childhood toys are and how meaningful their memories are. In another episode, it turns out that Luke is attached to Kenny the Koala because he was the only family he had at the orphanage. Although, it seems a bit Harsher in Hindsight and hypocritical considering that Jessie and co. spent much of the episode trying to separate Luke from him.
The plot point of the episode guest starring NBA All-Star Chris Bosh, who plays for the Miami Heat, has Luke trying to and seemingly suceeding at washing Chris's lucky socks, rendering them useless and causing Bosh to lose all of his skills, so the Knicks can beat the Heat. Considering that television episodes are typically shot at least 2-3 months before their air date, the episode was more than likely shot before the 2012-13 NBA season had started. New York and Miami have played each other twice between filming and the air date, and the Knicks won both games.
Add to that Lebron not scoring 20 or more points in a game for the first time all season right around the time of the promo started running and that the Knicks got off to one of their hottest starts to the season in franchise history makes its even funnier.
In "Where's Zuri?" Jessie called Hudson (played by Matt Shively) "her with man hands" after learning their backstories were the same. In and of itself funny, even funnier when you learn Ryan (Matt Shively's character from True Jackson VP) was teased a lot for his girly physique.
Ho Yay: In "Somebunny's In Trouble", Brett is Mistaken for Cheating on Emma, leading to a fight when she finds out he's been hanging out with Luke behind her back, her brother being referred to as "the other woman" up until the reveal. Their behavior and Brett's conversations with Emma and Luke that follow are similar to that of a soap opera when one is caught cheating, background music and all.
Luke: There's only one thing to do. Brett, I don't think we should see each other anymore. Have I cherished our time together? Yes, but... it's over.
Brett: Luke, no!
Luke: We'll always have the Jets game.
Brett: Luke, don't be rash.
Luke: I said it's over!
This is prefaced by a scene in which Emma discovers Luke wearing Brett's football jersey.
Mrs. Rhoda Chesterfield crosses this at least twice: First time she crossed it was when she yelled at Jessie and calls the Animal Control to get rid of Mr. Kipling, merely because Jessie's cookies broke her tooth. She crossed it again in Glue Dunnit: A Sticky Situation by breaking Luke's football.
Agatha crosses the line by oppressing nannies and trying to blackmail Jessie with doctored photos to get her fired.
Darla especially crossed it in the past, by throwing Jessie down a well!
From the same episode, losing track of a child under your supervision must be unbearable when you consider what happens to most missing kids. Zuri even says to Jessie when they find Emma and Ravi, something along the lines of "I told you they would still be alive".
Replacement Scrappy Series: Some people had this attitude when Jessie first premiered regarding Suite Life on Deck. Note that people also thought the same when On Deck replaced Suite Life of Zack and Cody.
Zuri to some, for her annoying, bratty attitude. She Took a Level in Jerkass in later seasons, with few heartwarming moments in between For example, she blatantly mismanaged and neglected Ravi's baby lizards when he asked her to babysit them and still demanding that she be paid for it. Also, in "Caught Purple Handed" she lied to partygoers, saying a really famous celebrity would be there, but once Emma and Luke opposed the fact she lied, she immediately insulted them and made them fix her problem.
Bertram to others, even though he can be portrayed sympathetically. Although, it's been lessening lately, due to the fact that everyone Took a Level in Jerkass toward him.
Then there's also Mrs. Chesterfield, who is just inexcusably awful to the core. Considering how other characters treat her though, this may be intentional.
That almost was the case but very early in development it was felt that making it a formal Suite Life spin-off would be too much of a distraction and take away from the Suite Life on Deck finale.
Squick: The Ross kids' reaction to Bertram and Jessie when they mistakenly believed Bertram was proposing to Jessie. Quite possibly many in the audience, too.
Unintentionally Unsympathetic: It's hard to act sympathetic for the kids at times, considering that they're selfish half of the time (especially Zuri).
What an Idiot: In "Trashin' Fashion", Christina fails to identify Kitty Couture as Emma. Y'know, her only biological daughter.
At the end of "Used Karma", Jessie & the kids are scared by a robed figure who is very obviously Bertram.
Jessie during "G.I. Jessie." What could possibly have made her think that bringing Luke to a military base where experimental weaponry is kept was a good idea? She was practically begging him to make trouble.
The Woobie: Jessie - Debby's acting and facial expressions really sell it. Bertram also gets more than a few moments of Woobie-ness.
Ravi gets a lot of Woobie moments too, especially in Are You Cooler Than a Fifth Grader? and pretty much whenever Mr. Kipling is in trouble. Like Debby, the actor reallysells it. Additionally, if anyone's going to get hurt in a scene, it's usually Ravi.
Stuart gets hit with this pretty hard. He really likes Zuri, but is unintentionally stalking her. Zuri doesn't even give him a chance and openly degrades him in public even though he's done a lot of stuff for her. She made him do a lot of this stuff; she's actually using him.
Jerkass Woobie: All of the main characters get at least one turn at this, typically by being selfish but repentant brats (yes, including Jessie).