Why Modern Times is the ultimate Bob Dylan guessing game

What is Bob Dylan thinking? What passing thoughts move through his head? I consider this often, though I’ve learnt over time not to wonder it out loud. The rabbit holes it leads conversations down are inescapable. Regardless, partly due to his unwavering determination to never let any of us know exactly what’s going on up there, it’s a question that has been thrown around out of awe, bewilderment and genuine accusation for just shy of 60 years now.

How typical, then, that Dylan would finally concede to offer us a glimpse while we were at our most off guard. “Today is the day I’m going to grab my trombone and blow,” he announces in the opening exchanges of “Thunder on the Mountain”, the first track on 2006’s not particularly culturally in-focus Modern Times. As we lean in hopefully, awaiting the momentous event of long-awaited revelation, he unveils: “I was thinking about Alicia Keys”.

With that, we partly wished we’d never asked. But inside this gesture is the seed that makes Modern Times such a quietly inspiring piece of work. While his alumni of classic songwriters attempted to prove themselves ahead of or inside a time they no longer bore relevance to, at the turn of the new century Dylan decided that his Modern Times was a bubble that would apply to him alone. The album sits in a strangely soothing blend of numerous old worlds, while Dylan gives himself freewheeling license to bizarrely reference the contemporary pop culture he was living alongside.

The resulting music, some of which is liberally lifted from other people’s songs over the years, is so ancient sounding that it aesthetically predates even that of Dylan’s youth. On “Thunder on the Mountain”, he continues his aforementioned fascination with the contemporary soul singer, going on to wonder “where in the world Alicia Keys could be”. Then suddenly, on “Spirit on the Water,” the poignant piece of faded edged nostalgia that immediately follows, he is a man with a voice loaded with the multiple lives it has lived, singing about a rekindled romance over a wilting piano line.

This is the see-sawing with which Modern Times lodges itself into your psyche: between the cowboy ramblings of a rock’n’roll outfit you probably have very vague context for and the wistful memory of a jazz bar you think you might have seen in a David Lynch film. “Nettie Moore” sits in there as a work of broken and untouched genius the same way “Make You Feel My Love” did, until Adele brought it to a different audience, while Dylan’s odd interaction with modernity continues with Scarlett Johansson’s appearance in the video of “When the Deal Goes Down”, where heartbreak lives in every other line: “We live and we die, we know not why/ but I’ll be with you when the deal goes down”.

On its release, Modern Times was all I listened to for a while. Its landscape of inhospitable escapism, where you’re never sure where you stand, was imprinted into my every day. It gave me an excuse to occasionally check out from the actual modern times of the mid-Noughties, and the high-octane, seismic guitar records of that summer that The Maccabees were beginning to reach for (Arctic Monkeys debut, Yeah Yeah Yeahs’ Show Your Bones, Hot Chip’s The Warning, and so on). When Dylan rolled through town on the Neverending tour, I was dutifully there and ready to absorb. I giggled at “Like a Rolling Stone” being entirely undecipherable until the third chorus, like I was in on the joke with Dylan, before he sucker-punched me with an equally unrecognisable rendition of Modern Times centrepiece “Workingman Blues 2,” a song he had only just released. He’s always one step ahead like that.

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As I winced and strained to make out the refrain, a small part of me pleaded with him to give me some rope. I was, in truth, trying desperately hard to stay onside. My girlfriend came too. She was, understandably, trying less hard. Her only take away from the event, as we left the doors and I felt myself swelling with a feeling of welcome disorientation, was that “he was taking the piss”. We never spoke of it again. To this day, I construct what my response should have been in my head, the one that would have changed her mind.

I won’t ever get that moment back, but fortunately Modern Times is with us forever and in my sole moment to talk you round, I would encourage you towards the record, carefully but unconditionally. It isn’t Dylan’s best record by a long stretch, it might not even be in the Top 20. It is probably bettered by his previous album, Love And Theft. Its magic, though, is in Dylan’s continued insistence on coming out punching and weaving while admitting that the numbers are no longer on his side. His remarkably cryptic way of doing so, with a previously untapped vulnerability, in turn frames the entire catalogue into some kind of inexorable conclusion for any Dylan fanatic.

The record’s great spirit of positive contrariness was echoed by his release of a 17-minute epic about JFK’s assassination this week. As everyone scrambled to hash out videos with (incredibly well meaning) statements of togetherness, there was somehow a greater feeling of comfort in knowing that Bob was still out there being Bob. Modern Times was a tipping point of similar, if subtler, comfort, certainly to me: I sensed Dylan was never going to let anyone second-guess a) whether he was taking the piss or, in any bland and candid sense, b) what he was thinking. Even if it was just about Alicia Keys, after all.