'Winnie the Pooh' Movies To Watch When You Need Something Wholesome

Release Year: 1977

The Story: The Many Adventures of Winnie the Pooh combines several stories based on the original A. A. Milne books. It includes Winnie the Pooh and the Honey Tree, which focuses on Pooh getting stuck in Rabbit's door while trying to acquire honey, Pooh and Piglet becoming friends while braving a storm, and Rabbit getting irritated by Tigger constantly tackling everyone. The stories are knitted together with a larger plot that involves Christopher Robin starting school and not having as much time with his animal friends. 

Why It’s So Darn Cute: If you're looking for an old-school Winnie the Pooh flick, this is the way to go. The stories are cute, and the overarching theme of loss and new beginnings is both poignant and ultimately uplifting.

Release Year: 2000

The Story: When Tigger starts to feel like he doesn't fit in with his friends, he sets out to find other Tiggers who are just as rambunctious as he is. Owl suggests that Tigger find his “family tree” - an idea that tigger interprets to mean a literal striped tree surrounded by other Tiggers. When his plan doesn't work, his friends forge a letter from his family and even dress up as Tiggers to try and make their friend happy. Unfortunately, this kind gesture backfires when Tigger realizes it's a ruse and becomes heartbroken.

Why It’s So Darn Cute: In the end, Tigger realizes that even though he might be different from those around him, they love him for who he is. Not only that, but they'll go to great lengths to help him. He doesn't need to find another family, because he already has his friends.

Release Year: 2011

The Story: After trying and failing to find a suitable replacement for Eeyore's missing tail, the friends realize that there's something else missing, too - Christopher Robin! Thanks to misunderstanding a note that Christopher Robin left, saying he'd be “back soon,” they come to the mistaken conclusion that he's been kidnapped by a terrifying beast called the “Backson.” They try to figure out how to rescue him. Meanwhile, Pooh is all out of honey and can't focus on trying to rescue his friend. 

Why It’s So Darn Cute: This animated theatrical release is a more modern take on one of A. A. Milne's classic stories. It involves the characters misunderstanding things in a hilarious but adorable way, without really focusing on sending a message… except the lesson that sometimes, the biggest fears and anxieties are rooted in misunderstandings.

Release Year: 2005

The Story: A frightening creature called a Heffalump has been spotted in the Hundred Acre Woods. Pooh and the others go looking for it, leaving Roo behind because it's too dangerous and he's too little. Roo ends up finding the Heffalump before anyone else, befriending him. When the rest of the gang comes back, they think that the Heffalump is a threat and try to save Roo, but in the end, Roo manages to convince them that he's not dangerous at all.

Why It’s So Darn Cute: This story is all about the consequences of making assumptions. Everyone assumes that Roo is too little to do anything, but he ends up being the person who figures out the truth. They also assume that Heffalumps are inherently dangerous, which causes them to be mean. They learn that you shouldn't be so quick to judge - an important reminder that even adult viewers might need. 

Release Year: 2018

The Story: Most Winnie the Pooh movies focus on Pooh and his other animal friends, but this live-action film follows Christopher Robin (played by Ewan McGregor) instead. After growing up, Christopher Robin leaves the Hundred Acre Wood for London, where he begins working in the corporate world. He then gets married and has a child. Things aren't going particularly well for him, but his life changes when Pooh reappears in London. At first, Christopher Robin is mostly concerned with getting Pooh home, but he soon realizes that his childhood friend is just what he needs to fix his life.

Why It’s So Darn Cute: While anyone can enjoy this film, it's likely to appeal the most to adults who grew up watching Winnie the Pooh. After all, who doesn't want to believe that the magic of childhood is still there, waiting to be rediscovered, even in adulthood?

Release Year: 2003

The Story: Piglet is excluded from trying to get honey out of a bee hive because he's supposedly too little to help. He gets the bees into a new hive, but nobody notices, so he gets upset and leaves. As his friends look for him, they look through a scrapbook and remember all the times that Piglet solved problems or helped out, even with his small size. They realize that they were wrong, and apologize when Piglet returns. 

Why It’s So Darn Cute: Piglet doesn't always get the appreciation he deserves, and this movie does a great job of remedying that. Piglet's friends think he's too small to accomplish anything, but when they go through their memories, they realize that he may be little, but he's done some pretty big things. 

Release Year: 2002

The Story: The friends try to celebrate New Year's Eve at Rabbit's House, but they end up creating various forms of mayhem and getting on his nerves. He gets fed up and claims that he wants to leave the Hundred Acre Woods. Everyone decides to use their New Years' resolutions to change their quirks so as not to irritate Rabbit so much. This results in their swapping personalities - Tigger becomes timid like Piglet, Pooh becomes depressed like Eeyore, Eeyore becomes obsessed with honey like Pooh, and Piglet becomes full of energy like Tigger. This only annoys Rabbit more, so he storms off - only to be attacked by bees, which his friends must rescue him from. 

Why It’s So Darn Cute: Ultimately, Rabbit realizes that he should be more appreciative of who his friends are, and not try to change them. After all, even if they can be annoying, they risked their safety to save him from the bees. It's a great reminder that everyone has their flaws, but friends can be forgiving of each other's personalities.

Release Year: 1999

The Story: Seasons of Giving features three separate stories: Groundpiglet Day, A Winnie the Pooh Thanksgiving, and Find Her, Keep Her. To some degree or another, all of them involve Rabbit being overly controlling with his friends and needing to learn to let go. The first involves Piglet pretending to be a groundhog for Groundhog day, declaring that winter will end soon, upsetting Rabbit when it continues to snow. In Thanksgiving, Rabbit insists on having a traditional holiday, which is ultimately ruined before being salvaged by the true meaning of the holiday. Meanwhile, Find Her, Keep Her is about Rabbit's attempts to stop a bird named Kessie from learning how to fly because he thinks that flying is too dangerous. 

Why It’s So Darn Cute: Like many Pooh stories, there are lessons here regarding Rabbit's desire for control. He has to accept that not everything can go according to his plan, and that he can't protect everyone from harm no matter how much he might want to. Rabbit's behavior is among the hardest for the friends to deal with, so it's nice to see him working on it - and still being loved and accepted despite it.

Release Year: 2002

The Story: It's Easter, and everyone is trying to celebrate the holiday - except for Rabbit. Rabbit doesn't want to celebrate Easter and replaces it with Spring Cleaning Day. He demands that his friends spend the day cleaning his house. When they put up Easter decorations along with the cleaning, Rabbit gets so angry that he throws them out of his house. This turns out to be a reaction to the previous Easter, when Rabbit tried so hard to control the holiday that his friends wandered off and did it without him. Feeling excluded, he blames the holiday instead of his own behavior. 

Why It’s So Darn Cute: This movie is focused heavily on Rabbit, who goes through a major arc. He learns that if he wants to be close to others, he needs to loosen up a little and not be so obsessed with everything going his way. In the end, he does celebrate Easter with his friends, and he focuses on what will make everyone happy - not just himself. Also, as the title implies, Roo plays a big role as well - he's so exuberant about Easter and so committed to helping Rabbit overcome his issues that it's totally heart-melting. 

Release Year: 2001

The Story: This movie takes an anthology format, as Pooh, Tigger, Piglet, Rabbit, Eeyore and Kessie literally pop out of the "Book of Pooh," which is in Christopher Robin's bedroom. As they wait for Christopher Robin to show up, they experience the stories - one dedicated to each character. 

Why It’s So Darn Cute: Each individual tale has its own charms and lessons. Kessie's story, for example, focuses on the importance of life-long learning. Meanwhile, Tigger's story involves him trying to give up sleeping so that he won't miss out on anything fun. These episodes showcase the characters' personalities in a fun, fresh way.

Release Year: 2005

The Story: While preparing for Halloween, Tigger tells a story about the Gobloon, a scary creature that turns bystanders into Jack-o-Lanterns - but if you catch it first, it will grant you a wish. Not everyone believes that the Gobloon is real, but the appearance of a shadowy figure and of a Jack-o-Lantern that looks like their Heffalump friend Lumpy makes them think that the Gobloon is real. 

Why It’s So Darn Cute: Because it's a Halloween movie, this flick is a tiny bit scary, but all of the spooky bits are explained away by something wholesome. Kanga is setting up a Halloween party, and she's been making Jack-o-Lanterns that look like all of her friends - that's why one looks like Lumpy. 

Release Year: 2010

The Story: This TV film is one of three based on the Playhouse Disney series My Friends Tigger & Pooh. When a magical space rock lands in Rabbit's garden, it enlarges his vegetables. Pooh, Tigger, Darby, and Buster eat the vegetables and gain super powers. They decide to use those powers to become superheroes, though they learn that their powers aren't necessarily permanent. 

Why It’s So Darn Cute: At the end of the film, the vegetables go back to their usual size, and the Super Duper Super Sleuths lose their powers - but that doesn't stop them from saving the day. Instead, they use their innovation to remove a boulder that's trapping Lumpy and Roo. They realize that powers are great, but what's more important is being able to adapt to circumstances and try their hardest no matter what. 

Release Year: 2007

The Story: A reindeer named Holly appears in the Hundred Acre Wood. She says that she's looking for a magic bag that must be returned to Santa Claus. The Super Sleuths help her out, and then join her on her mission to return the bag to Santa.

Why It’s So Darn Cute: Many Winnie the Pooh movies feature a major life lesson. Those are great, but sometimes viewers just want to have fun without a big takeaway. If that's the goal, this movie gets the job done - it's simply an adorable Christmas tale to get the holiday spirit going.

Release Year: 2009

The Story: Rabbit is elected mayor of the Hundred Acre Wood, and the power of the position goes to his head. He institutes a bunch of rules that nobody can follow - particularly Tigger. Fed up that Tigger isn't doing what he wants, Rabbit divides the town in two, claiming that he'll control one side and Tigger will control the other. This works out terribly, since everyone is separated from their friends and nobody can trade resources. After the pressure of a storm and some help from Darby, Tigger and Rabbit make up and reunite the town.

Why It’s So Darn Cute: It's always nice to see people with different personalities getting along. Tigger and Rabbit are frequently at odds due to Tigger's free-spirited nature and Rabbit's controlling one. It takes a lot for them to put their differences aside, but through this movie they learn the importance of accepting others as they are.