So I went into this book without realizing that it started out as a blog. But after figuring that out, I still don't really understand the point of making a book out of it. The format itself was a bit annoying, because you flip back and forth from the picture/quote page to the background/connection page in the back, which made actually reading the book kind of a pain.
Also, while the quotes fit the context of the media reference, some of the connections seemed pretty shallow and there wasn't really any analysis included. It was a good starting point to get people thinking, but I think you'd have to be pretty obtuse to not think about some of these things in the first place. Taylor Swift is paired with, "Above all, she was the girl who 'feels' things." Enough jokes have already been made about that on the Internet, I don't think this one really added anything to the discussion.
So while it was a unique idea, I think the execution was a little dull. If you subscribe to Thomas C. Foster's idea that "there's only one story", these connections are really not that big of a leap. Teenagers from Pretty in Pink (1986) and The Brief Wondrous Life of Oscar Wao (2007) feel the same? What are the odds?