“Oh boy, somebody has a vaguely contrarian stance on Bob Dylan,” you’re thinking. “It’s like being on Blogspot in 2008,” you continue, “and this is the part I accidentally read for 5 seconds before I found the Megaupload link to Metal Machine Music because I wanted to hear it, right, but it felt like too much of a homework assignment to actually buy.”
“And one more thing,” you say, getting louder and incorporating hand gestures, “the last time anybody needed a contrarian opinion about Bob Dylan was the early 1970s, when he was starting to get too famous. Not in his old age, when he’s settled comfortably into that ‘mildly alienating historical icon’ groove he’s been in since the Dharma & Greg cameo.”
And you know what? You’re right. That stuff’s all true. But don’t worry. You already clicked on this. You blew it. It’s all over now. Just let it happen.
I will always be apprehensive about Bob Dylan, largely because I came from a Merle Haggard family. This meant Bob Dylan was, to the extent he got acknowledged at all, a San Francisco thing that got out of hand. By the time I started listening to him in college, at the behest of dudes who wore sweaters, it was already a bit too late. He struck me as a poseur. He had a fake name and a fake voice; academics wrote books about him that you could cite in grad school; boring people called him Dylan; psychos called themselves Dylanologists.
And he wrote songs about the working class that existed too neatly in a preexisting literary canon. It all seemed like Working Class Reappropriation Theater, but I listened to him anyway, because I don’t give up on homework assignments, I just fail at them. I couldn’t figure out the albums people got longwinded about, especially Blood on the Tracks and The Basement Tapes. Those are a locked door to me now, and the key is evidently held by boomers “with a creative side,” so I’m content to leave them be. And I don’t go for the canonical stuff much at all, except for occasional songs here and there, or Before The Flood, which succeeds on standalone grounds as a big bombastic live rock album with Levon Helm harmonizing.
But the second he realized he was an old guy, instead of an actor pretending to be one, I was on board without reservations. His old guy albums are consistently satisfying because they resist critical pretention. Analysis rolls off them. There’s only so much you can project onto a guy who builds songs around the Mannish Boy riff without irony. This makes them easier to digest as music. There’s no subculture pegged on Old Bob Dylan. It’s just a songwriter and his band settled into a comfortable road-hardened groove. Except for “Not Dark Yet,” none of the newer songs seem like they could anchor a sad montage in a Best Picture winner.
The first Old Bob Dylan album, of course, was Time Out of Mind. Shadows In The Night,
On some level this sounds nakedly ridiculous, because Bob Dylan didn’t preserve his voice. Where Tom Waits sings like he’s putting on a one-man revue as an Omniscient Hobo, Bob Dylan routinely sings like he actually has cancer. (See: “Pay In Blood.”)

But it works to this album’s favor. Frank Sinatra’s versions of these songs all sound like they cost a million dollars, like listening to them requires formalwear and knowing the right club owners. They’re too Hollywood. The singing is perfect and the arrangements are gold-plated. They feel like historical curiosities in 2015. Stock music for period films. Dylan undoes all that here, leaving only their wistful and forlorn character.
Shadows in the Night is the Frank Sinatra mood without the Frank Sinatra aural environment. Where Frank Sinatra’s version of “I’m A Fool To Want You” sounds like a song you might hear at 2 a.m. on Sunset Blvd., Bob Dylan’s version sounds like something you might hear at 2 a.m. in an Arizona border town.
The key to this, which is consistently effective, is that Dylan has swapped out Sinatra’s big-budget orchestra and replaced it with a pedal steel and a band that’s falling asleep. The arrangements are smoke in the air, dusty horns and creaky floorboards. They feel as lonesome as the lyrics seem to say they should. And to that end, Dylan’s ragged voice is consistently an asset. These are weary performances of weary songs.
This is not an album of variety. No slow songs are turned into fast songs. There’s no electric guitar stomp or rewrites or genre shifts. There are no songs “rescued from obscurity and brought dizzyingly into the 21st century.” This is simply a dignified mood piece, and the mood is lonesomeness and pining heard from someplace far away. It’s almost ambient; something best heard too quietly, from the window of a neighbor’s house or on the jukebox of a bar with a dirt parking lot. There are no statement songs or sly political commentaries, just a surprisingly humble take on the American songbook. That’s all there is to say about it, and it’s a quiet victory, the kind rarely afforded to artists who have been around as long as Bob Dylan.