Top 10 Winnie the Pooh Moments That Made Us Happy Cry

Any longtime “Winnie the Pooh” fan knows that Heffalumps can be frightening monsters...that is until we got “Pooh’s Heffalump Movie”. Despite never actually seeing one, Pooh and friends believe Heffalumps to be terrifying beasts. Thankfully, their beliefs change towards the end of this movie, after Lumpy and his mother help free Roo from the pit of logs. This was a delightful way to show us that it’s unnecessary to fear the unknown, and that you should never judge someone for being different. Now, how about those Woozles, huh? When do we get to know more about them?

While Roo and the gang are busy planning an Easter surprise, Rabbit shows up with an angry look on his face. All they wanted to do was give him the best Easter ever! Just when we think he’s going to let them really have it, Rabbit gives them all Easter decorations and gifts. Eeyore even gets a bunny tail! Before they begin the egg hunt, Roo tells Rabbit what they were doing - fixing up Rabbit’s beloved Easter hat. Rabbit, why are you crying?? Now you’re making us cry!! This was just too adorable to endure!!

As we get older, it gets really tough balancing our time between work and family. Unfortunately, our grown-up Christopher Robin tends to spend too much time working. We see the toll it takes on his family, too. His daughter is frustrated, and his wife feels she’s lost the man she fell in love with. However, its this conflict that makes the ending more heartwarming when Christopher Robin finally realizes his family is more important than some business meeting. It’s a sweet moment that also serves as a reminder that we should always dedicate time to our loved ones… as well as take a break from work every now and again.

Rabbit doesn’t exactly have much patience when handling his friends. Unfortunately, in “A Very Merry Pooh Year”, Rabbit has reached his limit and begins making plans to leave the Hundred-Acre Wood. Pooh and company try their best to change for Rabbit, but only end up making things worse. However, when Rabbit learns they were trying to keep him from leaving, he has a change of heart, acknowledging what makes them unique. It’s an endearing lesson in accepting your friends for who they are, even if they occasionally get on your nerves.

Families aren’t always made defined by genetics; they can also be formed by bonds of love. After surviving a ferocious snowstorm and rescuing his friends from an avalanche, Tigger loses his family’s letter. This is where the waterworks start up… everyone begins reciting parts of the letter, making Tigger finally realize who his family was the entire time. This kind gesture shows that nobody is ever truly alone so long as you have friends who, in a way, are an extension of your family. You don’t need to be related to show you care about someone!

During the hero party celebrating Pooh supposedly rescuing Piglet, Eeyore announces he has found a new home for Owl. Unfortunately, Owl’s new home turns out to be Piglet’s. Despite this, Piglet is willing to let Owl take it without much concern about where he’ll continue to live. Bothered by this dilemma, our chubby little cubby tells Piglet he’ll be living with him and asks Christopher Robin to make the party a “two-hero party”. There aren’t too many people who are as caring as Pooh, and it shows just how far Pooh is willing to go to keep his friends happy. We love you, you silly, old bear!

We suppose you could say “Christopher Robin” is a bit of an emotional roller coaster for some of us adults. Don’t judge! This is especially true during Christopher Robin’s return to the Hundred-Acre Wood. As Christopher and Pooh watch the sunset, Christopher tells Pooh that he is lost, referring to his struggle to bring back his former self. Our lovable Pooh Bear simply responds with, “But I found you”, and the two embrace each other. Pooh may be a bear of very little brain, but he always seems to know what to say.

Piglet spends so much time being scared and nervous that we can’t help rooting for him to be more brave. Luckily, he had that moment in the spotlight towards the end of “Piglet’s Big Movie”. To commemorate him for his daring rescue, Pooh and friends throw Piglet his own “hero party”. In addition to the several drawings made by his friend, Piglet’s name is placed on the “Pooh Corner” sign, now called “Pooh and Piglet Corner”. Our pink pal may be tiny, but he’s got an incredibly big heart, and his friends are more than happy to show their appreciation for him.

We all want to see our friends smiling. Although, when it comes to Eeyore, we trust he’ll find his own happiness. However, we can’t blame Piglet for being concerned. While Piglet tries to explain his intentions, Eeyore shows him why he spends so much time alone on the hill. Turns out Eeyore enjoys cloud painting; and it isn’t long before Pooh, Rabbit, Tigger, and Owl join them. Seeing everyone gather around Eeyore and participate in his favorite activity puts a smile on our faces and tears on our cheeks. Sometimes, good friends are all you need!

Before we open the floodgates with our top pick, here are a few Honorable Mentions:

Rabbit Reunites with Kessie
“Seasons of Giving”

Roo Releases Lumpy
“Pooh’s Heffalump Movie” (2005)

Christopher Robin Brings His Family to the Hundred-Acre Wood
“Christopher Robin” (2018)

As much as we enjoyed the firefly scene with Pooh’s song, it’s the ending of “Pooh’s Grand Adventure” that really gets the waterworks flowing. Christopher Robin tells Pooh about his experiences at school and how the thought of Piglet, Tigger, and Pooh helped him get through his day. He then tells Pooh that he’ll have to go back. To solidify their friendship, the two promise to be together forever and ever, even when they’re a hundred years old (or in Pooh’s case, 99!). Now, doesn’t that just warm your heart? We’re not crying, you’re crying! (Okay, we’re crying!)