Jake Doyle (Neil Patrick Harris) is a man who's daughter Annie (Sophia Reid-Gantzert) wants nothing more than a cellular phone for Christmas. However, John doesn't seem to be in that much of a hurry to get one. Instead, he brings her home and has her play games with him on his Nintendo Entertainment System. Being a kid, she has no idea what to make of it. So, Jake decides to tell her a story.
Back in the 1980s, Jake Doyle (Winslow Fegley) was just another kid in the neighbourhood. He had his friends Teddy, Mikey, and Evan, and had to put up with The Bully Josh Jagorski, and local rich kid Timothy Keane (Chandler Dean), who was the only kid in the neighbourhood to own an NES, and made everyone in the neighbourhood pay him exorbitant prices to get the honour of... watching him play it. As soon as Jake saw the NES in action, he knew he had to have one. Of course, his parents aren't too keen on having some electronic distraction box in their house. Undeterred, Jimmy makes it his mission to get the NES for Christmas.
The films provide examples of the following tropes:
- Adaptation Distillation: The movie reshuffles the timeline of events. For example: The last-minute switch from a Nintendo to Encyclopedias was initiated by the toy and book store that donated it due to over-demand of the console. In the film it's a direct result of Timmy Keene's TV-shattering tantrum.
- In the book Jake isn't present for the TV-incident and only hears about it second-hand. In the movie he sees it in person having snuck in to the basement via the dog door.
- The Gruseki twins (the Hodges in the movie) win the wreath selling contest in the book, not Jake.
- In the book several of Jake's friends actually do get a Nintendo for Christmas, having received it through grandparents or Aunts/Uncles, only Jake is left out. In the movie no one does.
- All for Nothing: The Wreath selling contest ends up a bust when the Nintendo is switched out for an Encyclopedia set at the last minute. Also the mall heist ends in disaster when Jake slips on the ice outside and a bus runs over the dropped Nintendo. Jake never does get his Nintendo for Christmas. He works all summer to afford to buy one instead. However...
- An Aesop: Jake remembers this Christmas as one of the best, because it was the Christmas he learned to really understand and appreciate his family and it was the Christmas he discovered his favorite thing to do with his dad.
- If you want something you need to work for it. Just make sure that it's really worth the effort you're putting in.
- Blatant Lies: Jeff Farmer is constantly lying for attention.
- The Bully: Josh Jagorski
- Actor Allusion: Neil Patrick Harris stars as a character who tells a long, winding story about his youth that is ostensibly about how he found a great love but is actually a coping mechanism to help him deal with the grief of losing a family member.
- Chekhov's Gun: The ice in front of the mall entrance.
- Jake mentions trap doors when his dad tells him about the forts in the woods he built as a kid. sure enough, the treehouse he builds Jake is accessible through a trapdoor.
- The Encyclopedias that Jake wins in the wreath-selling contest help him plan the Mall heist and also inspire his sister's love of Australia, where she lives as an adult.
- The cut up hockey sticks Jake's dad makes him varnish become the trapdoor on the treehouse his dad builds
- Diving Kick: When Timothy Keane tries showing off his new Power Glove, only to find it doesn't work, he gets so frustrated that he does a flying kick right at the TV. The end result: the screen gets cracked, and the TV falls over on his tiny dog. (thankfully, the dog survived, albeit it did have to get many casts)
- Empty Chair Memorial: John's place at the dinner table in the present day.
- Failure Is the Only Option: No matter what Jake tries to get an NES for Christmas, the universe of the movie just seems determined to keep that from happening. In the end, the universe wins.
- Foreshadowing: Early in the film Jake calls out for his wife "Kate." Later on it's mentioned that he has the same boots as Katie Sorrentino. It's revealed in the final scene he married her.
- After their first argument about the cell phone Jake says he just wants his daughter to have a good Christmas, to which she asks him if it's possible that he could have a good Christmas. Jake's father had recently passed away.
- Framing Device: The main character as an adult, telling the story to his daughter. Establishes him as an Unreliable Narrator in the trailer; he's not sure if it was 1987 or 88 and when asked by the girl about bike helmets he says "of course we all wore them in the '80s" with the film's "reality" instantly changing to reflect this.
- Also the Bill Ripkin card that plays a minor role in the story was released in '89.
- Generation Xerox: Adult Jake has clearly picked up some traits from his father, like his obsession with making good time on the road and aversion to giving his children technological distractions.
- Moral Guardians: Dr. Timothy Keane Sr., who convinces the community to ban video games after Timmy destroys his TV and injures his dog in the process.
- Never My Fault: The Keene's blame video games for their son's destruction of the TV and injuries to their dog, rather than their own Hands-Off Parenting.
- Scout-Out: The "Loyal Ranger Scouts" in the movie for the book's Cub Scouts.
