Earlier quoted context omitted.
I explain the title, and the intended tone and purpose of the book series, in the preface. If you wouldn't mind taking the 3 minutes to read it, I'd be curious if it changes anything about your opinion of the title: https://github.com/getify/You-Dont-Know-JS/blob/master/prefa...
Having played the "You Don't Know Jack" PC game from 1995 I found the title playful. From your preface I see you'll be doing exactly what I wanted from a book with this title. Going into all the areas I never would in a programming language. Not just how but why. I agree with the GP though, on feeling some fatigue around people telling me I'm doing something wrong. Eating food, reading a book, tying my shoes, putting…
These are what the covers of all the books in the series look like:
http://shop.oreilly.com/product/0636920026327.do
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side note: my kickstarter for the books, 2 years ago, playfully used the bald head image to catch people's attention (never the intended branding). I soon afer got a friendly lawyer takedown notice from the folks who own the game. We worked it out, and the new branding was born. :)