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  • Awesome Art: As per usual for Disney's eighties cartoons, some of the episodes look amazingly close to the original film's quality for TV budget, especially the early episodes produced by TMS or Disney's Australian unit.
  • Accidental Innuendo: In "No Rabbit's a Fortress", Tigger tells Pooh and Piglet that he will lead them past the booby traps, and follows it with, "Tiggers is experts on trappin' boobies, y'know!"
  • Awesome Music/Ear Worm: The theme song. It was so kicking that all agree that the theme song is one of the best things to come out of the franchise. It's likely a whole generation of kids who grew up watching One Saturday Morning, the Pooh videos or other reruns have the theme drilled into their heads.
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    • The closing credits instrumental version of theme song, particularly the extended version with humming and just a bit of vocals at the end. The early instrumental closing credit version of the song (with more trumpets) is no slouch either.
    • Many of the music cues and background songs.
    • The pirate song from the beginning of the episode "Rabbit Marks the Spot". It is one of the most awesome and fun pirate songs ever.
    • "Nothing's Too Good For A Friend" was cheery and catchy enough to make it into a later sing-along compilation.
    • Tigger sings a brief but utterly heart wrenching little number about his identity crisis during the climax of "Stripes". The score building up to it is even more moving.
    • Pooh's "Here We Go Floating" song that opens "Balloonacy" is absolutely sweet.
  • Big-Lipped Alligator Moment: Private-Ear Tigger's Disney Acid Sequence in "Eeyore's Tail Tale", which comes completely out of nowhere after Pooh hires him to look for his missing "Bee Tickler", and accomplishes nothing after it's done, with not one word being said about it, leaving audiences to wonder "What was that all about?"
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  • Bizarro Episode: A fair few episodes step out of the usual laid back antics of the original film and books and take a far more surreal tone, most notably "The Piglet Who Would Be King", "Cleanliness is Next to Impossible" and "Sorry, Wrong Slusher.".
  • Ensemble Dark Horse:
    • Nasty Jack, a literal horse, from "Paw and Order", to the point where he's playable in M.U.G.E.N.
    • Kessie from "Find Her, Keep Her". Everyone remembers Kessie. This is probably why she was promoted to main character in The Book of Pooh.
    • Stan and Heff from "The Great Honey Pot Robbery" have quite a following, too, if DeviantArt is anything to go by.
  • "Funny Aneurysm" Moment: In "the Wishing Bear," the rest of the gang tries various ways to jog Pooh's memory when he forgets the rhyme needed to make a wish Christopher Robin's wishing star. The plot of the gang trying to help Pooh's memory was played much more seriously in Kingdom Hearts II when the Heartless tear pages of the Winnie-the-Pooh book out, which causes him to lose his entire memory.
    • For similar reasons as the above, the episode "Tigger Got Your Tongue?" had the characters thinking Pooh's honey, Tigger's voice, and Rabbit's vegetables were stolen by a "Nobody", with talk of whether "Nobodies" existed or not being frequent in the episode.
      • The premise of Tigger having his voice "stolen" also has heartbreaking undertones considering Paul Winchell by that point had to trade the role with Jim Cummings due to failing health and was eventually retired from the character altogether in 1999.
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    • Pooh's cries to find the wishing star in "The Wishing Bear" become this when in Pooh's Grand Adventure, he similarly begs for the wishing star during his heart "Wherever You Are" - because he's "empty and [cold], and [his] heart's about to break".
    • The end of "Ground-Piglet Day" has Rabbit reveal that it's actually November 13th, which prompts Tigger to exclaim "November 13th!?" and gasp in horror, asking "Do you realize what this means?" He then goes on to say that it's "Porcupine Day", but after the November 13th of 2015 and the terrorist attacks on Paris, his intended over-the-top reaction to the date comes off as much more uncomfortable.
    • The episode "Owl In The Family" has Owl realise he's become so estranged from his anecdote-spawning family that he questions if they exist, with Pooh and the others taking measures to initiate a family reunion to cheer him up. It's Played for Laughs and everything turns out alright in the end with a surprise visit from Owl's relatives. A few years later however another member of the wood would suffer the same dilemma...
  • Genius Bonus: In "No Rabbit's a Fortress", Gopher mentions that he has U235 in his arsenal of explosives.
  • Harsher in Hindsight: Several episodes deal with the theme of growing up (especially "Grown, But Not Forgotten"), and the theme would receive the most focus in the Darker and Edgier Pooh's Grand Adventure: The Search for Christopher Robin. That film in general makes many of the moments in this series between Pooh and Christopher Robin much more bittersweet, as in hindsight, you now know that those precious moments are on borrowed time before Christopher Robin grows up and can't come to the Hundred Acre Wood regularly anymore.
  • Heartwarming in Hindsight: "A Bird In Hand" shows Kessie return to the Hundred Acre Wood, now fully grown and no longer in need of Rabbit's affection. Later works such as Season of Giving and Book of Pooh however show Kessie having made returns to the Hundred Acre Wood while still adolescent, showing Rabbit didn't miss out on all of Kessie's childhood.
  • Hilarious in Hindsight: "Tigger Got Your Tongue" has Tigger lead the others in pursuit of invisible "Nobodies" stealing things. Sixteen years later...
    • Two ditzy friends, one with a mostly red and another mostly yellow color palette, go on adventures that get on the nerves of their neighbor, a stuffy green-colored fellow with Super OCD. Did we just describe Pooh, Piglet, and Rabbit, or SpongeBob, Patrick, and Squidward? It's even more hilarious since Tom Kenny, the voice of SpongeBob is the new voice of Rabbit as of the 2011 Winnie-the-Pooh film.
    • "The Monster FrankenPooh" is a bit amusing when you found out about Attack on Titan. Yes, Pooh becomes a Titan in this episode.
    • In "A Knight to Remember", Piglet searches for a dragon, which turns out to be Eeyore. Nearly 30 years later, one of the stories in The Best Bear in All the World plays out the same way.
    • The Imagine Spot from "Grown, But Not Forgotten" shows what Christopher Robin's adult life would be...although it's nothing like what would happen several decades later.
    • The episode "Cleanliness is Next to Impossible" would not be the last time that Jim Cummings plays a monster that lives under the bed.
  • Ho Yay: In "Un-Valentine's Day", Tigger is first to play the romantic lead in the valentine Rabbit is directing, but when Rabbit tells him he's got to kiss Kanga, Tigger is disgusted and refuses. Rabbit pushes for it, and Tigger agrees to do the kiss...but then immediately leans over and kisses Rabbit instead. Also, in "No Rabbit's a Fortress", Tigger lamented about how he hadn't given Rabbit a "good bouncin'" in days, saying, "I feel an empty spot in my life."
  • Memetic Mutation: From "Tigger Got Your Tongue": 'Looks like polar bears eating marshmallows in the snowstorm'note 
  • Signature Scene:
    • The ending of "Pooh Ought to be In Pictures," with Pooh and Christopher Robin on the hillside as fades to nighttime, is so significant and iconic, that it is the title card and closing credits of the series.
    • The Cloud Painting Scene from "Donkey for a Day" that it serves as the emotional climax of the series intro.
  • They Wasted a Perfectly Good Character: The show introduced a lot of original cast members who usually only made one or two appearances. Even some franchise regulars like Kanga and Roo only appear sporadically.
  • Tough Act to Follow: While Pooh's follow-on series have their fans, The Book of Pooh and My Friends Tigger and Pooh are often considered paler shows compared to New Adventures due to its impressive hand drawn animation, loyalty to the original film, clever emotional writing and wider scale target audience. The series set such a ground for Pooh works that some consider even the later feature length films inferior. The latter series even more so since Owl is completely removed.
  • Visual Effects of Awesome: The 'Cloud Painting' scene at the end of Donkey for a Day.

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