As an artist who had already reinvented himself several times over the years, Bob Dylan’s 1997 rebirth turned out to be not only his greatest comeback but also the greatest third act in rock ‘n’ roll history.

Partly inspired by his own mortality, partly inspired by his own mythology and partly inspired by whatever goes on inside Bob Dylan’s head, Time Out of Mind is a milestone in a career that’s had plenty of them over the past five decades. But it’s not like the then-56-year-old singer-songwriter was at a total career standstill at that point.

After stumbling through most of the ‘80s with one mediocre record after another, Dylan teamed up with producer Daniel Lanois on 1989’s Oh Mercy, his best album in at least a decade. He followed it up with the next year’s Under the Red Sky, a peculiar, but not altogether unpleasant detour, and a pair of albums – Good As I Been to You and World Gone Wrong – made up of traditional songs arranged by Dylan.

He also launched his Never Ending Tour around this time, which sparked his live performances and in turn inspired him in the studio. At the start of 1997, he got back together with Lanois, and with some studio vets they worked their way through more than a dozen songs, 11 of which ended up on Time Out of Mind (outtakes are on The Bootleg Series Vol. 8 – Tell Tale Signs: Rare and Unreleased 1989–2006).

Before the album’s release, Dylan ended up in the hospital with a serious heart condition. When Time Out of Mind finally came out on Sept. 30, 1997, the album’s centerpiece, "Not Dark Yet," as well as a few other tracks, suddenly seemed like an old master’s musings on his near-death experience, even though the songs were written and recorded before he got sick.

Whatever the case, Time Out of Mind was Dylan’s best album in decades. It was immediately praised by both critics and fans, reached the Top 10 and won a Grammy for Album of the Year. From the opening "Love Sick" (which bears Lanois’ atmospheric production) to "Cold Irons Bound" (Dylan’s toughest song in years) to the 16-minute closer "Highlands" (a stream-of-consciousness romp that name-drops Neil Young),

Time Out of Mind was the work of an artist who still sounded like he had something to prove to the growing list of cynics. The album’s legacy carries on to this day. It spurred a creative renaissance in Dylan that’s yielded solid, if occasionally overpraised, works like Love and Theft, Modern Times and Tempest. These past years have been Dylan’s most fertile period since his mid-‘60s peak, a streak no other comeback artist has been able to sustain. Plus, Time Out of Mind gave us another one of his ever-changing vocal quirks. This one was informed as much by the dark, despairing music as it was by age. In a way, Dylan's raspy, worn-out voice is the near-perfect symbol for his near-perfect album.

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