In the Magical Galactic Kingdom of Nottingham, Skeeter Bronson is an unappreciated warrior from Greece. Well, not really.

In reality: Skeeter Bronson is a handyman in a hotel, in which he's been working for 25 years. Ever since his dad owned and ran it. In fact, when his dad sold the hotel to Mr. Nottingham (starting a hotel empire), Skeeter was promised to one day run it. Or so he hoped. You see, despite being a fabulous worker for the same hotel (well, two different buildings, but that's beside the point) he has been recently passed up to be the manager of the third building in that specific hotel's lineage within the empire.

Meanwhile, Skeeter's sister, Wendy, needs to travel to Arizona in order to find a Job. She asks Skeeter to watch over her two kids during the night, while Wendy's friend Jill takes the day shift.

With nothing to do at the kids' home, Skeeter starts to tell bedtime stories in order to entertain the kids. These stories vary in theme, from AncientGreece to SciFi. The kids often throw in events to mix up the story, coming up with better stuff than Skeeter's RealLife events. When the events the kids throw into Skeeter's story affect Skeeter in real life, Skeeter uses this to his advantage.

This film is entirely unrelated to the 1979 GameShow produced by MerrillHeatter and Bob Quigley. Nor does it have anything to do with the Music/{{Madonna}} album of the same name.

!! This work provides examples of:

* BettyAndVeronica: Blonde, sweet heiress Nicole vs. the practical brown-haired teacher Jill.
* {{Cloudcuckoolander}}: Skeeter. Just watch the scene where he introduces Mr. Nottingham to the audience.
** It only makes sense that another [=Cloudcuckoolander=], Mickey, has to "translate" for him after his tongue gets stung by a bee at Mr. Nottingham's party.
* CorruptCorporateExecutive: Kendall. Seriously, [[spoiler:the guy wants to blow up a school to make a new hotel, going over the foreman's head to check the building when Wendy can't find Bobbi and Patrick, who were ''in'' said school that was going to get blown up]], and taunts Skeeter repeatedly throughout the film just because his dad's hotel wouldn't have stayed open without Mr. Nottingham's intervention.
* DerailedFairyTale: The kids interrupt Skeeter's stories with their own wild ideas-- with the added twist that everything they suggest actually happens.
* DiabolusExMachina: Happens InUniverse in Skeeter's last story. After he wins in his story, the kids add that he gets incinerated, because, apparently, [[CallBack it's more real]], much to his frustration.
* HappilyEverAfter: Happens, but not in the way you expect.
* HerCodeNameWasMarySue: Subverted in the first story. In other stories Skeeter keeps trying this, but the kids keep interjecting, up to [[spoiler:"ruining" his final story.]]
* IdeaBulb: Skeeter is fixing the wiring on a lamp, and it just happens to come on when he realizes that the kids control the stories.
* ItsBeenDone: Kendall's theme for the new hotel was going to be rock and roll, but when Skeeter points out how the Hard Rock hotel has run on this theme for years, Mr.Nottingham gives Skeeter a chance to think up a better theme that can get him in charge.
* {{Jerkass}}: Kendall and Aspen.
* LargeHam: Guy Pearce seems to be having entirely too much fun as Kendall.
* LaserGuidedKarma: Kendall and his girlfriend, who relentlessly taunt and mock Skeeter throughout the film, [[spoiler:end up as the staff of Skeeter's new hotel at the end.]]
* MeatVersusVeggies: Skeeter's sister Wendy raises her kids on a strict vegetarian diet, e.g. a gluten-free wheatgrass cake that nobody eats at Bobbi's birthday party. Skeeter has trouble making them breakfast using various foods from her kitchen, asking "Doesn't your mother have tastebuds?", and later gets them burgers for dinner.
* NoCelebritiesWereHarmed: Creator/TeresaPalmer plays Violet Nottingham: a young, blond 20-something hotel heiress celebutante notorious for partying and winding up in the tabloids.
** Her father, Barry, too: a hotel billionaire with an extreme fear of germs.
* NiceJobBreakingItHero: Skeeter telling the kids that there are no happy endings near the beginning gets him fired near the end after the kids make a story with a bad ending, saying they want their story to be "real".
* PetTheDog: When Violet watches the kids for a minute early in the film, she is very nice, treats them well, and takes an interest in their romantic life. It is an early sign that Violet isn't a bad person, just a bit of a spoiled Daddy's girl with tabloid issues.
* PosthumousCharacter: Skeeter's father, Marty Bronson, who acts as TheNarrator.
* RainOfSomethingUnusual: The children that Skeeter is telling a story to interrupt his tale with gumball rain. Because the stories supposedly comes to life, Skeeter is caught in the middle of a gumball rainfall when he's driving home. The camera reveals that it's the result of a gumball lorry crashing into a pillar on the road above him.
* RomanticFalseLead: [[spoiler:Violet]]
* RunsOnIgnorance: The stories can only affect Skeeter if the additions are from people who don't know that it affects his real life.
* ShoutOut:
** In his story set in Ancient Greece, Skeeter shouts [[Film/TheWarriors "Can you dig it?!"]].
** In his last, sci/fi-themed, story, Barry Nottingham is dressed like [[Film/FlashGordon1980 Ming the Merciless]], and Skeeter is dressed like [[Franchise/StarWars Han Solo]] while Mickey's character spoofs C-3PO.
* SmallNameBigEgo: Kendall.
* WhereAreTheyNow
** [[spoiler:Barry Nottingham becomes the new school nurse for Webster Elementary after going to medical school.]]
** [[spoiler:Mickey and Violet get married, taking over Barry's hotel empire.]]
** [[spoiler:Skeeter and Jill officially get married.]]
*** [[spoiler:At the same time as Bugsy the guinea pig, who goes on to have a lot of big-eyed babies.]]
** [[spoiler:Kendall and Aspen end up working for Skeeter at his hotel.]]
* [[YourTelevisionHatesYou Your Radio Hates You]]: After the kids finish a story that has Skeeter's character set on fire and disintegrated, all the songs on Skeeter's radio have to do with fire.