How to get wildly into Winnie the Pooh: A viewing guide
Disney+ is home to a whole Winnie the Pooh cinematic universe. Here’s where to start and watch to watch.
Winnie the Pooh is an adorable 98-year-old little bear, the star of short stories and screen for more than 50 years. Along with pals and Hundred Acre Wood neighbors Piglet, Tigger, Eeyore, Kanga, Roo, Owl and Rabbit, Winnie has had oh-so-many adventures and learned oh-so-many life lessons, while also kind of being (endearingly!) the absolute worst.
We’re spending the day going wildly in-depth on the silly old bear, answering all sorts of what ifs (what if … the animals went to college? what if … they were Avengers?) and raising 103 new questions of our own. Such extensive Poohology must, of course, involve an thorough survey of the Pooh’s contributions to motion picture arts and sciences.
While a good wealth of Winnie content has always existed on YouTube in varying degrees of quality, Disney+ is, of course, a convenient place to find it all now. As we run through what to watch and where to start in the wide world of Pooh, the titles you see in bold are on Disney+ as-of launch. The rest will be there, presumably, eventually, because Disney owns everything.
The classic cartoons
Start your Winnie the Pooh content journey with The Many Adventures of Winnie the Pooh (1977), a compilation of Honey Tree (1966), Blustery Day (1968), and Tigger Too (1974) shorts. Then round out the collection with Winnie the Pooh Discovers the Seasons (1981) and Winnie the Pooh and a Day for Eeyore (1983) — both available in full on YouTube.
From there, return back to feature-film land with the trio of The Tigger Movie (2000), Piglet’s Big Movie (2003) and Pooh’s Heffalump Movie (2005) — which you might as well watch in order because there’s no good reason not to and the “solo films” as it were (they’re not really solo films) break up all that “Pooh and pals” action.
Then, however, circle back to Pooh’s Grand Adventure: The Search for Christopher Robin (1997), which brings everyone together to save ol’ C.R. while “confronting their insecurities” because this wouldn’t be Winnie the Pooh if all these adorable animals weren’t just psychologically devastated before being allowed to feel some semblance of self-confidence.
Now, this may be the time when you decide to move it along in your Hundred Acre Wood experience, opting next for a holiday narrative or a waking nightmare (more on this in a moment). However, if you are all-in on the classic cartoon style, you can keep the stories rolling with either The New Adventures of Winnie the Pooh (1988–1991) or Mini Adventures of Winnie the Pooh (2011–2014).
For something festive
All right. Let’s turn our attention to Winnie the Pooh’s holiday #content. Please consider this on a seasonal basis, as, given the sheer amount of Pooh, you really don’t need to watch a Christmas movie in July.
In any case, you’ve got Winnie the Pooh: Springtime with Roo (2004) for Easter, Pooh’s Heffalump Halloween Movie (2005) for Halloween, Seasons of Giving (1999) for Thanksgiving and Christmas stories and finally, A Very Merry Pooh Year (2002) for another Christmas tale.
The house on nightmare corner
So you’ve had enough of the sweet stuff and you think mm, this is nice, but what if I wanted to be more horrified than heart-warmed?
Well, then, buckle up for the aughts. (And also the ’80s.)
Start with the Disney Channel series Welcome to Pooh Corner (1983–1986) and/or the Playhouse Disney series The Book of Pooh (2001-2003), the latter of which also exists in a compilation film by the name of The Book of Pooh: Stories from the Heart that should have been subtitled Stories from Hell. Of a similarly upsetting style is another Disney Channel series, My Friends Tigger & Pooh (2007–2010), which also gave rise to the features Tigger and Pooh and a Musical Too (2009) and Super Duper Super Sleuths (2010) — all available for your everlasting horror.
Finally, if that is not enough there is Super Sleuth Christmas Movie (2007), nominally a Christmas movie but definitely a better choice for Halloween because seriously why was this such a popular style!!
Sad, sentimental and serious live-action(-ish)
Having survived…all of that, you may be looking for something more straightforward. You can, of course, return to the comfort of the classics listed above, but you may wish to set cartoons aside. Understandably so.
You have two options, you probably don’t need to watch both. The first is Goodbye Christopher Robin (2017) — a FOX Searchlight movie that Disney is likely to keep buried forever, but one that starred Domhnall Gleeson and Margot Robbie in a biopic of Winnie the Pooh author A. A. Milne. Your other, more fully fictional option is Christopher Robin (2018), which maintains some of the historical elements of Christopher Robin’s life — boarding school, war — but adopts the same general conceit as Mary Poppins Returns i.e. a grown man, formerly an idealistic youth, rediscovers his sense of wonder and becomes a better dad thanks to the return of some magical token of his childhood.
Winnie the Pooh
What a ride. But we have to end with something quintessentially true to Pooh: The aptly named, Winnie the Pooh (2011). Undoubtedly more bonkers than those delightful, adorable classic cartoons, it still strikes the right, heartwarming chords of silly and sweet. It won’t give you nightmares, there’s no unpleasant fur technology, but there is a sense of modernity that feels like the right way to end your journey through the Winnie the Pooh cinematic universe.
Dozens of Winnie the Pooh movies and shows are available to watch on Disney+.