It seems like an especially Gen X sort of fixation for this story. It was first published in the sixties so it was right in the wheel house for those of use born in the early 70's. I have met more than one hipster who had a Max tattoo, and only one of them happened to be named Max themselves. I knew a hipster couple who had a kid in the late 1990s, and they named their boy "Max". I am sure that the boy in the wolf suit was no small inspiration.
It was one of the last books, I ever remember an adult reading to me. I was in 3rd or 4th grade, and too big to have an adult read me a bed-time story. I was still living in Billings Montana, so I must have been 9, 10 tops. And I was spending the night at a boy's house who was the only child to a single mother, and who's name I cannot remember, but we'll call him Cam. Cam's mom was really mothering to him, you know bed time stories in the third grade, and all. I remember some of the other boys picking on him calling him a "momma's boy" apparently they had spent the night at Cam's house and got the bedtime story bit too, and also thought it was weird, and having the social graces of a 3rd grader decided to use it as a weapon of ostraciation. This is really the age when the negative parts of the animal begins to emerge in boys. Anyway this kid lived in a nice big house at the foot of the Rims in Billings.

The Rims are these huge Sandstone walls that surround one end of the city, it is a pretty cool spot for a 10 year old boy and his buddy to spend the day running around, digging, exploring, building forts, and havind dirt clod fights. And we had spent the day doing just that. That night after we had a fun dinner, probably hamburgers his mom cooked and watched "3-2-1 Contact" that was on location at a Kiss concert. Cam asked me if I liked Kiss, and I shrugged my shoulders because I had no real opinion on music then, that was still a couple years off, but he told me that he didn't like them because they were "a bunch of Satan Worshippers" which probably would've been my answer too.
That night as we were being tucked his mom came in and said I have three stories one of them was "Where the Wild Things Are". We were both very excited for the Wild Things even though we were like 10, and it was a "kiddie book". It was the most popular choice, and was read last.

Which leads me to the question what is it about Max, his mischief, his private boat, and the Wild Rumpus - that holds such an attraction and fascination? Since it is a picture book, of 20 or fewer pages and less than one paragraph of prose. It must be the artwork, which is awesome. Or is it something about Max, the hero, who is a bit of an anti-hero. He makes mischief and then threats: "I'll Eat You Up". As he is banished to his room he transforms it to land of terrible creatures who he tames and becomes their king, only to become unhappy and return to the land which banished him to find his supper waiting for him, and that it is still hot. Now is there some obvious metaphor about living with and conquering personal demons, and then returning to the world knowing you are king of the Wild Things, and could return there, if you wanted too, kind of like Ash from the Evil Dead Movies.
It's all a bunch of navel gazing, isn't it? Especially based on a movie, that probably should've never been made, from a beloved book, that is un-filmable. Last time I look forward to an adaptation like this I was severely disappointed. Looking at you Watchmen.
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