The 1998 Grammy Awards were just out of hand. The producers of the 40th Grammy Awards did their best to broadcast a staid, comforting awards show, but things just kept happening. First, Ol’ Dirty Bastard, furious over Wu-Tang Forever losing an untelevised rap award to Puff Daddy’s No Way Out, stormed the stage just as Shawn Colvin was coming onstage to accept an award, letting loose with an immortal tirade: “Puffy is good, but Wu-Tang is for the children!” Then, not long after, Bob Dylan, who would later win the Album Of The Year award for his big comeback Time Out Of Mind, was onstage performing “Love Sick,” that album’s raw, slithery opening track. In a very late-’90s decision, the show’s producers had surrounded Dylan with young and attractive people, all dressed in black, who were dancing subtly and awkwardly. Suddenly, a young man jumped out of that crowd, the words “soy bomb” scrawled across his now-bare chest, gesticulating wildly in grand look at me, look at me fashion. He managed a long moment of camera time before security finally dragged him offstage.

That moment went as viral as a televised moment could go in the pre-YouTube late ’90s. Local newscasters chuckled about it. Will Ferrell parodied it on SNL. For a moment or two “soy bomb” functioned as a verb, and Michael Portnoy, the young performance artist who’d staged the stunt, wrung as much notoriety as he could out of it. But watching that footage today, what strikes me isn’t the kid with the words on his chest. Guys like that will always do what they can to get attention; the Grammy producers had just unwittingly given one of them a stage. What strikes me is Dylan himself. Before Portnoy’s interruption, that had been a great Dylan performance — Dylan and his band all fully locked in, guitars quietly growling and purring, Dylan’s voice a rasping and decayed husk of the nasal twang that had helped make him famous a few decades earlier. And after Portnoy, it remained a great performance. Dylan didn’t react to the interruption at all. He didn’t stop singing or playing, and as security pulled Portnoy away, Dylan merely glanced at him, bored. This was nothing to Dylan. Dylan had already seen everything.

If Time Out Of Mind had a single message, it was that. Dylan was 56 when he recorded the album. That’s not even that old, but Dylan actively steered into the aging process. Rockers of his vintage — the Rolling Stones, say — had gone out of their way to present themselves as being spry young men for as long as they possibly could. Dylan, by contrast, was already a curmudgeon when he was in his early 20s. And with Time Out Of Mind, he made an album haunted by ideas of death and irrelevance. The album isn’t about aging, necessarily, but it’s the sort of record that you can only make if you’ve been some places and seen some things.

The Dylan of Time Out Of Mind was coming off of one messy period after another. He’d gone through the much-derided fundamentalist-Christian flirtations of the late ’70s and through a divisive synth-rocker stretch in the ’80s. He’d been a Traveling Wilbury. He hadn’t dropped an album of original songs since 1990’s Under The Red Sky, an album that nobody thought was the best Dylan album. (His other two pre-Time Out Of Mind ’90s albums, Good As I Been To You and World Gone Wrong, had both been collections of stripped-down traditional folk songs.) Dylan was still a live draw, but I don’t remember anyone thinking that he was still an artistic force. He was a boomer rock icon, and boomer rock icons simply weren’t doing their best work in the ’90s. (The only exception, really, was Neil Young, who Dylan shouted out on the epic Time Out Of Mind closer “Highlands.”) Dylan’s peers were out there working the state-fair circuit and scoring positive Rolling Stone reviews, and everyone was comfortable with that.

Dylan wasn’t comfortable with that. He wrote the songs that would become Time Out Of Mind in a heady blur during a Minnesota winter. When it came time to record them, he called up an old collaborator: Daniel Lanois, who had produced Dylan’s Oh Mercy in 1989. And Time Out Of Mind is probably Lanois’ masterpiece. He surrounded Dylan with sound, recording him in full-band sessions with massive groups of musicians, all of them somehow working in the pocket of the songs that Dylan had written. The sound of the album is gauzy and dreamy and faraway, all reverb and memory and atmosphere. It’s not a wall of sound, exactly — more of an undulating curtain. The music calls back to ancestral country and roadhouse blues, but it’s not a retro sound. Instead, it’s like Dylan and Lanois and the album’s musicians found ways to tap into old grooves in ways that felt horny and sinewy and new. Dylan himself reportedly didn’t like the sound of the album, and he would never work with Lanois again. (He’s produced all of his subsequent albums himself.)

At the time, the casual bleakness of that sound reminded me of Portishead, whose self-titled sophomore album came out on the same day as Time Out Of Mind. Like that group, Dylan and his collaborators were taking older sounds and giving them new contexts, shaping them into something slinky and dark. Both Time Out Of Mind and Portishead could serve as background music in coffeeshops or restaurants; they were certainly surface-level pretty enough. But if you listened deeper to either of them, you could hear sex and doom and despair. And in the case of Time Out Of Mind, most of that came from Dylan himself — both in the words he was singing and in the elegantly ravaged voice he was using to sing them.

Compared to the Cookie Monster mutter-growl that Dylan uses now, his voice was sharp and clear on Time Out Of Mind. But it was still a far cry from the sly and self-assured honk of his younger years. The Dylan of Time Out Of Mind allowed himself to sound lost and beaten-down and tired. And he sang about those feelings, too, about regrets and lost loves and the encroaching shadow of death. “I’m sick of love,” he spitefully spat on the opening track, “and I’m in the thick of it.” Later, in a more ruminative mood, he mused, “It’s not dark yet, but it’s getting there.” Then, on “Trying To Get To Heaven: “I’ve been all around the world, boys, and I’m trying to get to heaven before they close the door.” He wasn’t in doomsayer mode the entire time. “Make You Feel My Love” might be the simplest and purest love song that Dylan ever wrote, and it’s definitely the album’s most-covered song. (Billy Joel recorded his version of “Make You Feel My Love” before Time Out Of Mind even came out, and these days it’s better-known as an Adele song than anything else.) But Time Out Of Mind is an album with a mood, and that mood is a heavy one.

The album ends with “Highlands,” a strange and masterful ramble that runs nearly 17 minutes. It’s a song that nobody else would ever even consider writing. For much of the song’s sprawling length, Dylan describes a flirty encounter with a Boston waitress. He describes it in really deep detail for a really long time. Some of their exchanges are borderline inscrutable; she guesses that he doesn’t read “women authors,” and he says that, no, he reads Erica Jong. Others are tedious; there’s an endless stretch where she tries to get him to draw a picture of her and he keeps coming up with unlikely reasons why he can’t do it (“I would if I could, but I don’t do sketches from memory”). The whole thing reminds me of some of the scenes from Twin Peaks: The Return, the ones that stretch on so long, and so pointlessly, that you stop wondering what David Lynch is even trying to do and you just fall into the rhythm of them, hypnotized. Eventually, when the waitress turns around, Dylan slips out of the restaurant, walks out into the street, and looks around him: “All the young men with the young women looking so good / Well, I’d trade places with any of them in a minute if I could.”

Time Out Of Mind kicked off a career renaissance for Dylan. People once again realized that this prickly, elusive old weirdo was one of our most fascinating artists. The album only barely scratched the Billboard top 10 but still went platinum easily. It stole the Album Of The Year Grammy that probably should’ve gone to OK Computer. It got Dylan off the nostalgia circuit and into hockey arenas. (I saw him on the Time Out Of Mind tour a few months after I got to college. He wore a bright white suit, didn’t say a word to the crowd, and radiated a sense of presence like I have never seen.) A few years later, Dylan was mean-mugging cameras in Victoria’s Secret commercials. And Time Out Of Mind was influential in ways that went beyond Dylan’s own career. I’d argue that it provided a roadmap for aging artists on how to use wizened voices to capture imaginations. I hear echoes of it in the music that people like Tom Waits and Leonard Cohen released soon after. And anyone who was looking for an example of unflappable, grizzled cool only had to look at the way Dylan shrugged off the Soy Bomb incident.

Dylan carried that reawakened goodwill for the next decade or so. Dylan’s next two albums, like Time Out Of Mind, topped the Village Voice’s Pazz & Jop critics polls in their respective years, and the goodwill only dissipated when Dylan started pulling troll moves, releasing a Christmas album and an endless series of Sinatra tributes. And this might be the album’s greatest legacy: It made it impossible to ever count Bob Dylan out. As long as he still draws breath, I fully believe that he could stop recording Sinatra covers whenever he wants, that he could come back and make another record that’s just as powerful as this one.