Our story starts at the end, or at least it feels like the end. The great man is nursing a broken ego and a busted hand at home in Santa Monica. It’s 1987, and for 10 years or more he has tried both keeping up and checking out—sometimes at the same moment—while the world he once shaped has fixated on what he did in the ’60s. It has left him lost, his music an empty tangle. He’s thinking about quitting. Maybe just ­walking until he gets to a place where someone will point at the acoustic guitar slung over his shoulder and ask, “What’s that?”

That’s how Bob Dylan described it in his autobiography, Chronicles, one of the many ways in which he’s recently taken the reins of his legacy. Tell Tale Signs—the eighth volume of the erratic and fascinating Bootleg Series, exhuming his unreleased music—begins there, at the fitful start of his regeneration: Dylan is in New Orleans to record Oh Mercy with Daniel Lanois, a Canadian producer with a ponytail and a taste for mystical doses of reverb. Dylan’s real resurgence, Time Out of Mind, is still 10 years off, and Lanois will figure there as well. Among other things, Tell Tale Signs attempts to wrest those records away from Lanois, a meticulous mood maker whose perfectionism never jibed with Dylan’s spontaneity.

Unreleased takes from those two albums make up half of Tell Tale Signs, including two different versions of “Dignity,” a song Dylan—under Lanois’s whip—recorded 20 times for Oh Mercy­, then mothballed. “Whatever promise Dan had seen in the song was beaten into a bloody mess,” Dylan wrote. A woman there to catalogue the tapes left the studio in tears.

Struggle snuffed the life from many of these songs. Widely adored on its release, Oh Mercy sound  leaden and humorless now, rife with the dregs of Dylan’s biblical moralism. Yet here’s a rockabilly take on “Dignity” that makes moralism do the twist.

Each Tell Tale Signs CD opens with a version of “Missis­sippi,” recorded for then dropped from Time Out of Mind. That’s where Dylan and Lanois got it right, though not without more struggle. “He tried to convince me that song had to be ‘sexy, sexy and more sexy,’” Dylan later said. “I know about sexy, too.” Lanois wanted a cauldron of hip-shaking drums; Dylan needed only seductive pauses in his phrasing. More casual and less doom-ridden than anything on Time Out of Mind, both outtakes lope along with a lazy elegance. Genius.

There’s more genius, too: four live cuts, scattered between 1992 and 2003, that make you wish Dylan would release full CDs of those shows; four soundtrack one-offs, the best—“Can’t Escape From You,” yet another tale of ineluctable desire—from a movie Hollywood never made; a Robert Johnson cover left off the solo acoustic World Gone Wrong, doubtless because that album ­already had enough death and blood. This is the other story Tell Tale Signs lays out: Dylan as journeyman  writing songs to order, doing whatever it takes to keep on keeping on.

Eventually, the two stories came together: After his second go-round with Lanois, Dylan began producing himself. He recorded two masterpieces, Love and Theft and Modern Times, quickly with his touring bands, working up arrangements that sounded ready-made even when they weren’t. Just two cuts here come from those sessions, perhaps showing that he knew exactly what he wanted and left little behind. It may have been the first time in his career. “Always prolific but never exact,” is how Dylan describes his working methods in Chronicles. But that was just the first 60 years.  

DOWNLOAD “Dreamin’ of You,” “Red River Shore,” “Cocaine Blues (live)”