Between 1923 and 1928, two men collaborated on a series of four books - "When We Were Very Young", "Winnie-the-Pooh", "The House at Pooh Corner" and "Now We Are Six" - which have since become classics in the field of children's literature. This film tells the story of the men and how those books came into being.
| Actor | Role |
|---|---|
| CC.R. MilneHimself / A. A. Milne | Himself / A. A. Milne |
| EErnest ShepardHimself | Himself |
 David HorovitchYoung Ernest Shepard | Young Ernest Shepard |
| RRichard KayYoung A. A. Milne | Young A. A. Milne |
| SSimon HeeryNot listed | Not listed |
| MMargaret HeeryNot listed | Not listed |
| BBarbara BeatonNot listed | Not listed |