I've read (at least parts of) several of the titles in the "Popular culture and philosophy" series; unfortunately, despite the general value of this sort of work, the series is very uneven. This title, I am glad to say, being both an armchair philosopher and a semi-professional Bruce Springsteen fan, is among the best entries.
The best feature of this book is that each of the authors (among the chapters I have read so far) takes Bruce seriously as what he is: a rock n' roll musician and contemporary poet. There is no attempt to make Bruce into something he is not (this point is clearly made in the first chapter). Instead, the authors stay true to the themes and issues that Bruce himself explores in his songs. In contrast to many of the other books in the series, for example, there are no chapters concerning how Bruce does (or does not) capture some element of Plato's theory of knowledge. There are, however, chapters on the nature of work and labor, the importance of human connection, the nature of freedom, and the possibility of redemption. Anyone familiar with Bruce's music will recognize these themes in his lyrics and choice of material. These themes are, moreover, profoundly philosophical, regardless of whether Bruce's explorations are as 'deep' as those of professional philosophers. (Although I would insist, as do many of the authors, that Bruce's music, in a sense, has greater depth than any philosophical treatise could achieve.)
This book is also notable, among the "Popular culture" series, for its list of contributors, which includes several prominent interpreters of classic and modern American philosophy (particularly the pragmatist tradition). This list includes: Randall Auxier and Doug Anderson (editors and contributors), John Shook, and Scott Pratt. This is possibly the best selection of professional philosophers among any titles in the series (apart from Slavoj Zizek's contribution to "The Matrix"). But this selection is also important because there is a (mediated) connection between Bruce and classic American philosophy. Though I am not suggesting that Bruce has necessarily read James, Dewey, etc., I believe that both Bruce (and other musicians who could be classed in the same genre as Bruce - including perhaps Steve Earle, Tom Cochrane, John Mellencamp, and John Fogerty - call it 'heartland rock') and James et al. share common roots in the philosophy and literature of the American Renaissance: Emerson, Thoreau, Whitman, Melville...
A good book, in all - though definitely for a certain 'type' of Springsteen fan. There are chapters that should appeal to any fan, but, as I suggested above, one reason for Bruce's importance may be that he pursues philosophical issues in a profoundly non-philosophical medium.