This is your third album of standards in a row – Shadows in the Night was a big surprise and a really nice one. Fallen Angels was a sweet encore. Now you really upped the ante. Did you feel after the first two, you had unfinished business?
I did when I realized there was more to it than I thought, that both of those records together only were part of the picture, so we went ahead and did these.
Why did you decide to release three discs of music at once?
It’s better that they come out at the same time because thematically they are interconnected, one is the sequel to the other and each one resolves the previous one.
Each disc is 32 minutes long – you could have put it all on 2 CDs. Is there something about the 10 song, 32 minute length that appeals to you?
Sure, it’s the number of completion. It’s a lucky number, and it’s symbolic of light. As far as the 32 minutes, that’s about the limit to the number of minutes on a long playing record where the sound is most powerful, 15 minutes to a side. My records were always overloaded on both sides. Too many minutes to be recorded or mastered properly. My songs were too long and didn’t fit the audio format of an LP. The sound was thin and you would have to turn your record player up to nine or ten to hear it well. So these CDs to me represent the LPs that I should have been making.
What’s the challenge of singing with a live horn section?
No challenge, it’s better than overdubbing them.
You like to be spontaneous in the studio, but here you’re working with tight arrangements and charts. Did that require a new way of thinking for you?
It did at first but then I got used to it. There’s enough of my personality written into the lyrics so that I could just focus on the melodies within the arrangements. As a vocalist you’re restricted within definite harmonic patterns. But you have more control within those patterns than you would if there were no boundaries whatsoever, it actually takes less thought, hardly any thinking. So I guess you could call that a new way of thinking.
At any point in the recording did you say to the musicians, “Look, we have to change this on the fly – just follow me…?”
No, that never happened. If I did that the song would fall apart, nobody would be able to follow me. Improvising would disrupt the song. You can’t go off track.
Are you concerned about what Bob Dylan fans think about these standards?
These songs are meant for the man on the street, the common man, the everyday person. Maybe that is a Bob Dylan fan, maybe not, I don’t know.
Has performing these songs taught you anything you didn’t know from listening to them?
I had some idea of where they stood, but I hadn’t realized how much of the essence of life is in them – the human condition, how perfectly the lyrics and melodies are intertwined, how relevant to everyday life they are, how non-materialistic.
Up to the sixties, these songs were everywhere – now they have almost faded away. Do they mean more to you when you hear them now?
They do mean a lot more. These songs are some of the most heartbreaking stuff ever put on record and I wanted to do them justice. Now that I have lived them and lived through them I understand them better. They take you out of that mainstream grind where you’re trapped between differences which might seem different but are essentially the same. Modern music and songs are so institutionalized that you don’t realize it. These songs are cold and clear-sighted, there is a direct realism in them, faith in ordinary life just like in early rock and roll.
It’s hard not to think of World War II when we hear some of these. You were born during the war – do you remember anything about it?
Not much. I was born in Duluth – industrial town, ship yards, ore docks, grain elevators, mainline train yards, switching yards. It’s on the banks of Lake Superior, built on granite rock. Lot of fog horns, sailors, loggers, storms, blizzards. My mom says there were food shortages, food rationing, hardly any gas, electricity cutting off – everything metal in your house you gave to the war effort. It was a dark place, even in the light of day – curfews, gloomy, lonely, all that sort of stuff – we lived there till I was about five, till the end of the war.
Between the Depression and the war, people had to swallow so much pain that songs that might sound overly sentimental to us had tremendous resonance. A line like “as a man who has never paused at wishing wells” – it might sound corny to people who haven’t lived too much. Can you get inside these songs in your 70s in a way you might not have been able to in your 20s and 30s?
Sure, I can get way inside. In my 20s and 30s I hadn’t been anywhere. Since then I’ve been all over the world, I’ve seen oracles and wishing wells. When I was young there were a lot of signs along the way that I couldn’t interpret, they were there and I saw them, but they were mystifying. Now when I look back I can see them for what they were, what they meant. I didn’t understand that then, but I do now. There is no way I could have known it at the time...
... People called Shadows in the Night a tribute to Frank Sinatra. Did you know Sinatra had recorded all those songs when you put that record out?
Yeah, I knew he did, but a lot of other people recorded them as well, it just so happened that he had the best versions of them. When I recorded these songs I had to make believe that I never heard of Sinatra, that he didn’t exist. He’s a guide. He’ll point the way and lead you to the entrance but from there you’re on your own.
There is a famous story that you and Springsteen were invited to a dinner party at Sinatra’s house around the time you did that TV tribute to him. Had you met him before? Did you feel like he knew your stuff?
Not really. I think he knew “The Times They Are a-Changin’” and “Blowin’ In the Wind.” I know he liked “Forever Young,” he told me that. He was funny, we were standing out on his patio at night and he said to me, “You and me, pal, we got blue eyes, we’re from up there,” and he pointed to the stars. “These other bums are from down here.” I remember thinking that he might be right...
More - so much more - here at https://bobdylan.com/news/qa-with-bill-flanagan/