Collection of five animated films featuring the honey-loving bear and his friends from Hundred Acre Wood. In 'The Many Adventures of Winnie the Pooh' (1977) Pooh (voice of Sterling Holloway) tries to get to the top of a tree in order to steal some honey from the bees, but gets himself stuck instead. His chums manage to release him with the aid of a balloon, but Pooh then proceeds to get stuck in the door to Rabbit (Junius Matthews)'s house.

In 'The Tigger Movie' (2000) Tigger (Jim Cummings) is just getting in the way when Pooh (Cummings), Piglet (John Fielder), Roo (Nikita Hopkins), Rabbit (Ken Sansom) and Owl (Andre Stojka) try to prepare a home for their doleful friend Eeyore (Peter Cullen), so Pooh suggests that he go outside and play with some other Tiggers. Tigger thinks this a very foolish suggestion, as he is the only Tigger in existence - or so he thinks. In fact, this proves to be the start of an exciting adventure in which Tigger discovers his long-lost family members.

In 'Piglet's Big Movie' (2003) everyone learns it doesn't take somebody big to do big things. Piglet disappears into the Hundred Acre Wood after hearing he is just too small to help Pooh, Tigger, Eeyore, Roo and Rabbit with a honey-gathering scheme. To find him, everyone makes a plan to work together using Piglet's scrapbook for clues to his whereabouts. While searching, they realise how big a part Piglet has played in their many adventures together. 

In 'Springtime With Roo' (2004) it is the most beautiful spring day ever, with bees buzzing and flowers blooming. Roo (Jimmy Bennett), Pooh and Tigger are ready to laugh and play. But Rabbit expects them all to stay inside until every last bit of spring-cleaning is finished. 

Finally, in 'Pooh's Heffalump Movie' (2005) Pooh hears a strange noise in the woods and he and his friends are convinced that the dreaded Lumpy the Heffalump (Kyle Stanger) has come to the woods to do them harm. Pooh, Piglet, and Tigger set out to capture the beast, but Roo, who is told he's too small to join the search party, meets Lumpy face to face and discovers he's not the bad guy he's been made out to be.