Winnie The Pooh: Dreamcasting Christopher Robin
Disney's live-action train continues to roll, and one of the most interesting and yet mysterious [...]
Patrick Warburton as Eeyore
Patrick Warburton was born with a wonderfully unique voice and tone, and he already crafted a pitch perfect comedic foil in Disney's The Emperor's New Groove as Crunk. He should bring his heavy baritone next to the resident pessimist Eeyore, which if you just visualize any clip from The Tick you can more than see. If they could inject a bit of Warburton's penchant sarcasm and snark, this would be the perfect pairing.
The official Eeyore character description reads "Gloomy Eeyore is not a fan of much, other than eating thistles, but his loyalty wins the hearts of his friends every time he loses his tail."

William H Macy as Rabbit
William H Macy has exhibited some of Rabbit's OCD traits in past roles, and the tenor of his voice is a perfect fit for Hundred Acre Wood's carrot farmer. Macy has always embraced the odd, as he does every week on Shameless, and you can just see him yelling at Winnie the Pooh over his gorging of honey. Macy knows how to straddle the fence in likeability as well, so in one scene he can be yelling at someone and in the next you can't help but cheer for him.
Sounds an awful lot like Rabbit. Rabbit's official character description reads "Rabbit is often the self-appointed leader of the Hundred Acre Wood. He can be stubborn when his routine is interrupted, but Rabbit is always ready to hop into action whenever his friends are in need."

Freddie Prinze Jr. as Tigger
Freddie Prinze Jr. has amassed quite the resume when it comes to voice acting, including well-praised parts in Star Wars Rebels and Dragon Age Inquisition. Those were more serious roles mind you, but this would give Prinze Jr. the chance to flex his creative muscles. It seems to be in his range, and he could most certainly handle the challenge.
It was difficult to not pick Jim Cummings for this role, as he has voiced Tigger in the past. For the live-action Disney might want to lighten the load a bit on him, so going with a different Tigger seemed the way to go.
Tigger's official character description reads "Boisterous and exuberant, Tigger is wonderful and one-of-a-kind. He eagerly shares his enthusiasm with others—whether they want him to or not."

Craig Ferguson as Owl
This was an easy casting, as the perfect candidate was already in the role. In 2011's Winnie The Pooh movie, the role of the wise (and slightly haughty) Owl was played wonderfully by Craig Ferguson. While there were other candidates that could fit (like Nick Offerman to name one), Ferguson brings the perfect amount of crazy and fun to the role, and no one else had that.
Owl's official character description reads "Owl is considered a bit of a know-it-all, though his friends in the Hundred Acre Wood always seek his advice. Unfortunately, he often misses the mark."

Tom Holland as Piglet
Piglet is Pooh's best buddy and is a fan favorite due to his endearing yet anxious behavior. He's instantly likable, and you can't help but root for him. There's an actor at the moment that has those same traits, and that's Spider-Man: Homecoming star Tom Holland. His voice has the perfect amount of nervous energy to make Piglet really come to life and will go perfectly with his best friend Pooh Bear.
Piglet's official character description reads "Piglet may be small in size but he has the biggest heart in the Hundred Acre Wood. This soft-spoken, s-s-steady friend's generosity leads this timid character to some large adventures."

Winnie The Pooh
While the change was made to Tigger, there is no replacing the iconic Jim Cummings as Winnie The Pooh. It's not like having Peter Cullen voice Optimus Prime, and as long as he's still willing to do it, the part will always be his. There's no one who has the mix of curiosity and sweetness that Pooh has, and only one voice can bring that to life on the big screen. Make it happen Disney, make it happen.
Pooh's official character description reads "A loyal friend to his neighbors in the Hundred Acre Wood, Pooh is always willing to lend a helping hand."

Owen Wilder Vaccaro as Roo
Roo is full of constant energy, typical of being a young Kangaroo. Roo isn't onscreen as much as the others, but when he's on your eye typically drifts towards him. You need a voice that can be youthful while also commanding that same attention. Enter Owen Wilder Vaccaro, who still captured the viewer's eyes when onscreen with actors Mark Wahlberg and Will Ferrell. If he can do it there, he's a perfect candidate for the Hundred Acre Wood.
Roo and Kanga's official character description reads "Kanga is a warm, protective mother to little Roo. Her hands are full with her young son, a wild adventurer who is eager to go everywhere and try everything."

Vanessa Bayer as Kanga
Roo's mom Kanga is the most patient and understanding character in the Hundred Acre Wood, which you have to be to deal with all these weird neighbors. You need someone who can deliver a sweet line with an underlying tone of sarcasm, and SNL's Vanessa Bayer could work wonders with that role. Bayer can be compassionate one minute while dropping a hard hitting one-liner the next, and for in this modern retelling that might be the best way to go for the character.
Kanga and Roo's official character description reads "Kanga is a warm, protective mother to little Roo. Her hands are full with her young son, a wild adventurer who is eager to go everywhere and try everything."
