The 1990s had not been particularly kind to Bob Dylan. He began the decade with Under the Red Sky, a star-studded record with some strong songs that might be best remembered for “Wiggle Wiggle,” a nursery rhyme from hell. An MTV Unplugged set, a greatest hits collection, a 30th-anniversary concert, a bootleg series, and two sets of covers not only cemented him as a legacy star, but also suggested that this once ceaseless well of new American standards had perhaps run dry. But has there ever been a better jumpstart for the heart than love and losing it? 1997’s Time Out of Mind—a return to originals so strong and singular, and finished under circumstances so dire that it’s fair to call it a resurrection—says no. As the decade entered its second half, Dylan found himself holed up in his native Minnesota, writing reams of heartsick lyrics as the winter pounded outside. Months later, he rendezvoused in a New York City hotel with Daniel Lanois, the imaginative producer who had helmed the sessions for 1989’s strong Oh Mercy. Dylan read him lyrics, handed him a stack of old blues records he loved, and told him that he loved Beck, too. Might they do something with all of that? Yes, Lanois said, and set off to work. Their early sessions in California moved in fits and starts, prompting Dylan to move the entire operation to Miami at the start of 1997. One of the greatest rock ensembles ever assembled soon joined him—two supreme drummers (Jim Keltner and Brian Blade), dual Southern swamp legends (Jim Dickinson and Augie Meyers), and a murderer’s row of guitarists (Cindy Cashdollar, Duke Robillard, Bucky Baxter) among them. They moved with the flexibility of a jazz band, shifting keys, tempos, and textures as Lanois and Dylan tried to take these blues—these testaments to dark nights of the soul—to new places. The sessions were fraught and the tempers short, but they eventually succeeded, flying back to California with the blueprints of Dylan’s first masterpiece in at least two decades. As Lanois finished the record, Dylan nearly died from a rare fungal infection, acquired while motorcycling across the Midwest. That was a proper setting for the arrival of these 11 songs, many of which seemed transmitted from the doorstep of hell. Dylan swayed like a willow in brutal wind during the lugubrious “Not Dark Yet,” and mustered just enough strength to plea for the next phase of his life—whatever that brings or means—during the warped waltz of “Trying to Get to Heaven.” He is stranded and haunted during “Cold Irons Bound,” and obsessed but feckless during the gorgeous “Make You Feel My Love.” And in proper Dylan fashion, he ends with a nearly 17-minute epic saga, “Highlands,” in which he seems to float on the periphery of reality, so over it all he can’t even order breakfast. But with Grammy wins, bigger tours, and resuscitated sales, Time Out of Mind would throw open the doors on the next phase of Dylan’s staggering career, resulting in some of the best and most singular work of his life. Dylanologists remain divided over the legacy of Time Out of Mind—how does it square with the rest of his work? But it barely matters: For Dylan, it set up the next quarter-century of prolific and dauntless music.