Plot
The film opens up with Dennis and Mr. Wilson waking up and getting dressed at the same time. They then get out of the house before Dennis crashes his bike into Mr. Wilson. Mr. Wilson wakes up and realizes that he was having a nightmare. Dennis meanwhile gets his bike and races his enemy, Jack Bratcher to school in time for the Thanksgiving paegent. On the way, Dennis' bike falls apart and Dennis falls down which make Jack call him a loser. At the paegent, Dennis opens the turkey's cage assuming it was thirsty. When Dennis came back, the turkey was missing from its cage. The turkey flies around and makes a mess of the paegent and Jack's father, David Bratcher encourages his son to throw the bake sale products at everyone. Dennis' principal threatens Dennis' parents with Dennis Clauses and force them to pay for Jack Bratcher's insurance policies. At home, Henry tells Dennis that he must take responsibility for his situation. Dennis promised to work it out by washing windows. doing the dishes etc which Alice and Henry said no to at each suggestion.
A few days later, Dennis sends an email to Santa Claus to give him a new bicycle and attends the secret Santa event at his house. He pulls Mr. Wilson's name from the hat and starts wandering what to give him for Christmas. At school, Dennis creates a Christmas spirit list with Presents, Christmas tree, cookies, lights and Santa Claus. The next day, Alice takes a new gift wrapping job at a department store and takes Dennis with her. He creates some type of balloon with bows on it which an old lady sits on and gets stuck to her bottom. When Dennis attempts retrieve the balloon, the lady swings her purse at him and knocks down the Santa Claus set up around her. Alice takes Dennis away from the mall. Later in the afternoon, Alice leaves Dennis with Mr. and Mrs. Wilson who happily babysit him. Mrs Wilson had to run errands and left Dennis and Mr. Wilson alone for a few hours. Dennis wanders Mr. Wilson's house looking for the perfect gift for Mr. Wilson. However, he comes across Mr. Wilson's stamp collection and plays around with his stamps. Mrs. Wilson returns from her errands and finds Dennis not in the living room with Mr. Wilson. They go upstairs to only find Dennis ruining Mr. Wilson's antique stamps which made him extremely angry and not want Dennis anywhere near him.
Dennis' parents try to assure that Dennis is a good kid and tel him to think hard and he can figure out the right gift to give Mr. Wilson. Dennis then decides to give Mr. Wilson the Christmas spirit. First thing on the list was presents. Dennis and his friends went shopping for gifts to give to Mr. Wilson. When Dennis gives Mr. Wilson his gifts, he cheers up a lot and becomes happy until Dennis accidentally trips him and breaks his arm.
Second thing on the list was a Christmas tree. While Mr. Wilson was at the hospital, Dennis and his friends find a pine tree on the streets and put it in Mr. Wilson's living room through the window assuming he would be happy. When Mr. Wilson returns from the hospital, he sees the tree which was also when a whole bunch of cops showed up that night thinking that Mr. Wilson stole the tree. The cops then arrested Mr. Wilson.
The next morning, Mr. Wilson was bailed out of jail. The third thing on Dennis' Christmas spirit list was cookies. So while Mrs. Wilson went out to buy pills for Mr. Wilson, Dennis got to work by baking cookies for Mr. Wilson. When Dennis gives the cookies to Mr. Wilson, he eats them and cheers up. However, Dennis used a variety of unusual ingredients which gave Mr. Wilson food poisoning so he went back to the hospital to get his stomach pumped.
The fourth thing on the Christmas Spirit list was lights. While Mr. Wilson was at the hospital, Dennis and his friends find Christmas lights and put them on Mr. Wilson's house to make it beautiful. Later in the evening, Mr. Wilson returns from the hospital and is happy to see his house decorated with Christmas lights at first. But when the lights turned on, it started a fire. This made him angry and he forced Dennis' parents to pay for the damage caused by the fire.
The next day was Christmas Eve which was Dennis' last chance to find the right gift for Mr. Wilson. The Last thing on the Christmas Spirit list was Santa Claus. Jack Bratcher goes up to him saying that tomorrow is the day he would race against Dennis on their bikes. Later in the evening, Dennis takes the same Santa Claus from the mall and puts him at Mr. Wilson's house. However, Mr. Wilson becomes angry when he sees the Santa Claus stuck in his chimney and mispronouncing his name as Mr. Winston. Dennis then makes an apology card for Mr. Wilson but he loses his temper by telling him to stay away from him, his property and his wife. He also tells Dennis not to say Mr Wilson's name and that there is no such thing as Santa Claus. Dennis also hopes with his good deeds, that he will receive a new bicycle for Christmas.
Dennis leaves Mr. Wilson's house in tears which is when the scene switches to The Santa Claus in a police car. He magically escapes custody. He turns out to be The Angel of Christmas Past, Present, and Future who intervenes to help save Christmas for the Mitchell and Wilson families.
The Angel takes Mr. Wilson to his childhood home in the 1950s, where he runs to his bathtub to put his neighbor's model boats which he thinks are in the wrong place, when the nozzle breaks and floods the room.
The Angel then takes him back to the present, and Mr. Wilson sees Dennis's parents don't have enough money for presents as a result of having to hand over so much money to the Wilsons in order to fix the damage caused by Dennis's behavior. He also notices how depressed his wife is because she really wants to celebrate Christmas, but due to her husband's hatred for the holidays they are unable to; he soon realizes he must put an end to it.
Finally, the Angel takes him to the future, where it's bleak and the atmosphere requires SPF 800 sunscreen because of global warming since 2019. His house is abandoned, and Dennis is shown to be old, lonely, childless and having a dislike of Christmas (and, in the process, repeating what Mr. Wilson said to him — and other kids — about Christmas). Mr. Wilson realizes that what he had said was not true. It is the final epiphany that convinces Mr. Wilson to change his outlook on Christmas and makes him vow to celebrate Christmas with others.
Mr. Wilson then wakes up to find himself back in the present, and spreads his Christmas joy around the neighborhood; Dennis wakes up the next morning with a tree loaded with gifts. Mr. Wilson helps Dennis's parents with finances, talks to Dennis and cheers him up with holiday joy (while also apologizing to him for what he had said). Mr. Wilson and his wife have a big Christmas tree in their living room, and his childhood fishing pole was purchased online. Dennis races with Jack Bratcher on his new bicycle, and loses. Jack and Dennis became friends. And for the first time in 30 years, it snowed in the community.
The film ends with the Angel sitting on a roof reflecting on how much he loves happy endings before popping back to the North Pole, and the kids riding their bikes before Dennis accidentally crashes into Mr. Wilson.
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