Winnie the Pooh Characters Ranked

Tristan Ettleman
6 min readAug 4, 2018

I love that weird old raspy yellow bear Winnie the Pooh. His name is weird and his friends are neurotic and I just think the whole lot of them are hilarious and cute. In the event of the release of CHRISTOPHER ROBIN, Disney’s live-action interpretation of their franchise based on A.A. Milne’s books and characters, I’ve decided to rank the main Winnie the Pooh characters, of which there are nine. Of course, this is within the context of the Disney versions of these characters, not Milne’s original vision or the acclaimed Russian shorts from the early 1970s or any other adaptation. I’m also excluding the assorted additions from Milne, and Disney’s various shows and direct-to-video movies, TV specials, and special theatrical releases. And sorry, Gopher, you’re not a main character.

#9 — Christopher Robin

Sorry, Chris, you’re just a boring old human kid who keeps things on track and is endlessly cheery. I appreciate that your imagination is apparently responsible for all these animals getting up and moving around and talking and stuff, but you just can’t compare to your pals. Ewan McGregor, though. There’s worse casting for an adult version. Ewan’s a cool dude.

#8 — Rabbit

Rabbit, dude, you’ve gotta cool it. You’re so obsessed with your garden and keeping everything to a plan and all neat and tidy but you’re missing out on the present, man. Be present. Believe me, I get it. I have a tough time breaking out of my own head and just going with the flow. I assume you had some trauma that led you to believing the only way to take control is to stick to your preferences and plans and boss other people around. But that’s no way to live. I see it when you are kind to everyone else. Just let it out. In the meantime, though, you’re a total buzzkill.

#7 — Roo

Roo. My guy. You’re fun, but you’re kind of exhausting. I just don’t even really know what to think about you. I appreciate it when you’re around but sometimes you overstay your welcome. I hate to say it but it’s just kind of weird that I’m talking to you like this because you’re a fictional, animated kangaroo child. But since I’m sticking to this impromptu dialogue I weirdly started out on with Chris, I just gotta say I can’t really relate too much to a little kid at this point in my life. Sorry. I hope you have a great and fulfilling life and I really don’t have anything against you. I just think it’d be weird if we hung out.

#6 — Tigger

Tigger, you can be annoying as shit, but damn if you’re not fun. I love how you mispronounce words, man. That’s totally my kind of humor, I love to say words weirdly. It’s kind of a cheap type of humor, but it gets me every time. I also think it’s pretty impressive how you bounce around on your tail. Like, I’ve never seen a tiger do that. And I do appreciate that you’ve overcome, well, a tiger’s typical desire to just eat other living beings without discretion. Sweet. I’m sorry I called you annoying as shit. You’re just a lot sometimes.

#5 — Owl

Owl, your stories are so bizarre and I love them. You’re so posh and I dig it. I also just like owls, what can I say. I gotta respect the elder statesman of the Hundred Acre Wood. This might be a weird thing to say, but I just think…you’re well-designed. I don’t know how to break this to you, but you’re a cartoon character, and you kind of represent a great classic cartoon design of owls that really started with Disney in the first place, like in the ’30s with THE OLD MILL (1937). You look much more friendly then those owls though. Yeah, that’s a compliment.

#4 — Kanga

Kanga, you’re a strong woman and I really respect you putting up with this male-dominated wood. Shit, that sounded bad. I just appreciate how hard-working and kind you are and I think you’re doing a great job raising Roo. You’re just a pleasant person and I’m glad every time I see you. I kind of told Owl this, and I’m really not sure how he reacted, but…I also think you’re really well-designed. Like, you just look fun. I think you should be around more often! I know it’s not really up to you, but more Kanga is something I would never complain about.

#3 — Eeyore

Eeyore. Dude. I feel for you. I can tell you’ve got a lot of issues. Forgive me if I’m being too personal, but…have you ever thought about getting help? Therapy has really helped me lately, actually. I think it would do wonders for you. Because, believe me, I’ve been there, where you’re at. I like the little sardonic jokes, I really do, I make them all the time. But there’s a way to have that energy but feel more whole on the inside. I just want to help you Eeyore. Let me help you. I feel for you. I want to be your friend.

#2 — Piglet

Piglet, I swear I’m not coming on to you, but you’re just so fucking cute. I was just telling Eeyore, I get the depression, I do, but man, I really relate to the anxiety. I am nervous all. The. Time. Yeah. It sucks. It frays the nerves. I feel like I’m going to die at such an early age because my cells will have deteriorated, from stress, at a rate much faster than is normal for an average human. Anyways. I just really want to help you out, kind of like Eeyore, because you don’t have to feel like this all the time. Have you been to therapy? Also, what’s up with your stomach? Are you like part armadillo?

#1 — Winnie the Pooh

I don’t care if it’s too obvious, Pooh Bear, but you’re just the best. Your voice is hilarious. I appreciate your love for honey. I love honey too. You just seem so chill and I really need that energy in my life right now. Quite frankly, can we go for a stroll along logs and stuff and do nothing? I really just want to replace Chris if that’s OK, at least for a bit. He’s probably OK once I get to know him. But you, Pooh, you’re the coolest. So chill.

…Did I just go insane?