Winnie – The – Pooh: Gloom and Doom for Pessimists by A. A. Milne with decorations by E. H. Shepard (Review)

Winnie – the – Pooh: Gloom and Doom for Pessimists by A. A. Milne with decorations by E. H. Shepherd.

About the author


Alan Alexander Milne was born in London on the 18th January 1882. He served in both World Wars, joining the British Army in World War I and was captain of the British Home Guard in World War II. Milne was known at the beginning of his career as a playwright and a writer for Punch magazine but when he created the character Winnie the Pooh all his previous work was overshadowed by the success of Winnie the Pooh. He died in 1956.

About the illustrator


Ernest Howard Shepard was born in London in 1879. He worked for Punch magazine as a cartoonist and illustrator. He is best known for his illustrations of The Winnie Pooh books and The Wind in the Willows.


This gently-humorous collection of A. A. Milne’s most melancholy moanings will bring a smile to the face of even the grumpiest Eeyore.


Waiting at a check out with all the Christmas food shopping I spotted this book sat on the side. I saw that it had Eeyore on the cover, so I had to have it immediately, anything with Eeyore, I have to have. I did not even look to see what the book was about, a definite choice purely from looks, rather than content.

This book is very short but enjoyable. Each page has a beautiful illustration on and there is a phrase and a quote involving Eeyore to back up this phrase.


Sometimes you just don’t feel like sunshine and happiness…

‘And how are you?’ Said Winnie-the-Pooh.

Eeyore shook his head from side to side.

‘Not very how,’ he said. ‘I don’t seem to have felt at all how for a long time.’

‘Dear, dear,’ said Pooh, ‘I’m sorry about that.’


I loved this little book as it reminded me of reading Winnie-the-Pooh when I was little and to be honest as a child all I wanted to read about was Eeyore, although I liked the other characters they were never as good as Eeyore. The other element I enjoyed was the humour, the carefully chosen phrases that went with the quotes were excellent and at times they made me giggle.

Although I am not a pessimist like Eeyore, I did sympathise with him and agree with some of his feelings from this book. Sometimes we do not feel our best and having a bouncy happy person around does not help our situation.

The illustrations are as beautiful as I remember and they fit perfectly with all the quotes. I was a little disappointed with the ending of the book because it goes away from Eeyore, it just feels like the people who put it together ran out of ideas, I would have preferred for them to have finished the books sooner than what feels like rambling. Due to this reason I only gave the book 3 dragons. An enjoyable and quick read to sit down to when you have a spare five minutes.


Lady Book Dragon