Shadows In The Night - Bob Dylan (2015)
The Week of Bob Dylan That Has Been
I’ve been a fan of Bob Dylan’s music since I was a teen. I haven’t written about it much on my old blog and not at all yet on Substack. I figured it was time to let you in on why I’m so obsessed with the man, but I didn’t want to just pick a single record. So I’ve spent this week revisiting some of the interesting corners of his career, tracking some of the many different courses he charted for himself, and how it informed what came next.
Here’s what I came up with.
- Another Side Of Bob Dylan - the restlessness of the folk hero trying to break free
- Highway 61 Revisited - the rock star in full bloom
- Nashville Skyline - the country crooner
- Slow Train Coming - the longest post I’ve ever written, I’d bet, about Dylan’s turn to Christianity and how it intersected with my own upbringing
- World Gone Wrong - looking back at his roots, but with a more perspective and polish
- Love And Theft - the “modern” Dylan, even though this one is already 25 years old
We finish with yet another turn into something new
Dylan turned 85 this year, so it’s not hard to imagine that the 2020 Rough And Rowdy Ways album and the ongoing multi-year road show it has inspired are the final stop on the man’s seemingly endless run of reinvention and sharp turns.
But before that current version of Dylan–something approaching a circus conductor / sideshow huckster drawing you into a web of weird and lovely Americana–we got one more unforeseen turn: the man who had spent decades building huge parts of the rock lexicon since the 60s went on a lengthy exploration of the pre-rock American songbook.
This first record and its successor, Fallen Angels, draw very intentionally on songs not because they’re necessarily famous but because each was recorded by the master of the American songbook, Frank Sinatra, during his classic 50s and early 60s run.
As he’s done for most of the 21st century, he produces his own session and leans on his familiar live band musicians, adding a horn section to fit the sound of the elegant 50s pop he was chasing.
These selections are all slow and stately ballads. People unfamiliar with the journey were surprised at the time by how skilled and artful his phrasing and vocal technique was. But this came from a lifetime of absorbing Sinatra and other ballad singers he loved, as well as a run of albums with increasingly complex and ambitious vocal work leading up to this new tack.
There was a third installment of this thread, 2017’s Triplicate. That one was a bit different: not exclusively Sinatra-related songs, but three individually themed records curated with great care from well-known and lesser-known mid-century tunes to each evoke a certain feel.
With these records in view, Rough And Rowdy ways is a little less surprising. It’s full of powerful and playful tunes that build a sort of imagined past that maybe never quite existed but is far more interesting than what we got. After the last track, Lucky Old Sun finished this morning, Spotify auto-played I Contain Multitudes from Rough and Rowdy, and other then his idiosyncratically crowded lyrics I swear you might not notice that you changed records.
His touring since then has weaved a similar spell, marrying his own material old and new to some of these classic songs from before his time to take you out of time itself.
If this is the last thing we get from one of pop music’s greatest minds, we should still be happy.







