When I saw that Dylan had chosen to give his only interview (so far) to promote his new album of ten songs Sinatra recorded, sometimes more than once, it almost seemed like a joke, or one of those Dylan style quirky choices to confuse anyone thinking they've got him figured out.
But on the other hand it's pretty typical of Dylan: combining a seemingly deep commitment to making music and recording it, with a pretty savvy take on how to get attention from the audience he thinks the music might appeal to. And recording well known and more obscure American Songbook tunes Frank Sinatra chose to record in his time, when Dylan was a boy and young man, might be a sentimental and generational choice, but promoting it through an extensive interview with the magazine for seniors is smart business.
I've always had problems with Dylan since the first time I met him, before he had yet recorded, through a female mutual friend back in '61. My reaction afterward was to tell the girl I thought he was a phony. Which, of course, at the time, he totally was, making up stories about his background and present. But then when I heard his album BLOWIN' IN THE WIND a few years later, I was envious that someone almost my age (he's a year older) was getting a message I, and a lot of us, shared across much better than we were at the time.
I ran into him again over the years at parties and other places and didn't have much direct connection to him, and when I did he wasn't gracious or even nice. And I've heard stories from those who knew him better or worked with him etc. over the years and some of them said it was a great experience and others said he was a pain in the ass diva in some ways and not nice to them either.
But his musical endeavors nonetheless often impressed me, certainly for the first few decades of his career. I never went to see him perform until about twelve years ago at a concert he did with Willie Nelson and while Nelson was older he gave an audience-engaged show and sang well, while Dylan seemed to care less about the ballpark full of paying customers and sang as though he only had access to two notes an out-of-tune octave apart.
But in this new venture, SHADOWS OF THE NIGHT, what I've heard of it so far, and despite the criticism may friends rightfully have of it (i.e. he's often flat, singing out of tune, and who else wold be given the recording facilities of Columbia records with a voice like that, etc.) I have to say I'm struck by his sometimes compelling attempt to carry the original melody and to give the lyrics the force of innovative phrasing and meaningful interpretation.
The interview captivated me too (here's a link to the unedited long version), because it concentrates on his musical taste and intentions with this album, and despite his seemingly evening the score with other recording artists and justifying his choices over theirs, or his usual disingenuous insistence that he's only interested in the music and hates interviewers asking question about philosophy or politics when for many years he wrote lyrics about philosophy and politics etc.
So, despite his faults and the shortcomings of his I experienced, he managed to get me to care about his latest offering and to read the entire interview and in the end to feel engaged with him and his musical project in a way I wouldn't be if he hadn't used his usual trickster manipulation to get my attention and, I suspect, people like me, i.e. of his, our, generation. Be interesting to see what younger listeners might make of it, if anything.