The new tribute album Bob Dylan in the 80s: Vol. 1 comes with an unusually didactic goal, to redeem the “oft-maligned” “wilderness” phase of the singer-songwriter’s career—the lag time between his decade-plus as an unnervingly precise weathervane of American culture and his late-1990s renaissance as a dirty-grandpa sage of mortality, mischief, and musical memory.

Save for 1989’s Oh Mercy, his first collaboration with producer Daniel Lanois, Dylan’s 1980s records were dyspeptically reviewed and later lumped together as gawkily, half-heartedly crafted detritus. Dylan co-signed that account in his 2004 memoir Chronicles: Volume One: “The windows had been boarded up for years and covered with cobwebs, and it’s not like I didn’t know it”; “There was a missing person inside of myself and I needed to find him”; “I felt done for, an empty burned-out wreck … in the bottomless pit of cultural oblivion.”

Executive producers Jesse Lauter and Sean O’Brien want to rescript that story and have enlisted nearly two dozen (counting bonus tracks) hip-ish, young-ish artists, including Deer Tick, Blitzen Trapper, Glen Hansard, Elvis Perkins, and Widespread Panic. Dylanophile novelist Jonathan Lethem adds cred with a lively companion essay. And the team succeeds in its mission, less because of the mostly passable efforts on the record than purely in having posed the question: Does this material deserve all the manure that’s been slopped on it?

Like Lethem, I grew up with 1980s Dylan. I’d glommed on to the early topical-folkie albums in my mom’s collection, then fixated on my own acquisitions of the mid-1960s rock milestones, but 1983’s Infidels was the first Dylan record I got to hear as a contemporary event.

I loved it. “Jokerman” (covered nicely but unnecessarily here by Built to Spill) seemed every bit as vital as most of Desire, for instance. “Sweetheart Like You,” with its video centered on a middle-age waitress, felt like a sideways protest song about have-nots, at least amid the lux Duran Duran interiors of oiled-up MTV. (Craig Finn, the sardonic-populist leader of The Hold Steady, lays claim to that song on the compilation’s single most successful track.)

I paid less mind to Empire Burlesque, Shot of Love, and the next few albums because I was past my classic-rock stage and hunting down indie, cult stuff. It was the face-slapping flash of light that is 2001’s Love and Theft that finally drew me back. But Dylan’s other vaunted late-resurgence albums are actually mixed bags, too. To me the 1980s records sound no less enjoyable alongside them now.

It is all the same elusive, imaginative, incorrigible Bob, one of pop’s premiere devils of disguise, more a Madonna than the musical MLK he gets made out to be. (Madge has been a protest singer, too.) He paid for his almost-incomparable streak of youthful inspiration by being driven to outrun his own shadow, into drugs, booze, religion, depression, stylistic quirks, and flagrant commercial betrayals of his purist 1960s savior myth. His Super Bowl car ad this year was just another move in that Seventh Seal chess match against his own legacy.

Yet I am as tickled and perplexed by the lyrical turns in a lot of 1980s Dylan as I am anywhere else. Take 1985’s stadium-soul “Tight Connection to My Heart,” which in retrospect sounds startlingly like queer solidarity in the key of surreally plain D:

Well, they’re not showing any lights tonight, and there’s no moon

There’s just a hot-blooded singer, singing “Memphis in June,”

While they’re beatin’ the devil out of a guy who’s wearing a powder-blue wig.

Later he’ll be shot for resisting arrest

I can still hear his voice, crying in the wilderness

What looks large from a distance, close up ain’t never that big …

As for production, the kick drums and backup vocals are overmagnified, sure, but so were everyone else’s, and they were no less excessive than the strings on some of the 1970s records or the slide-guitar, soft-focus drowsiness of the later Lanois output such as 1997’s Time Out of Mind. All decades have their recording tics, and music lovers should embrace them with good-humored affection. And often Dylan sang better than he does now, too.

So if it wasn’t really the writing and performances that explain 1980s Dylan’s outcast status, what was it? I think it was deep cultural structure, on two fronts.

Rock began as music rooted in an awkward time of life, pitched to move adolescents and often made by people barely out of their teens. What sustained it and made it dominant was that in addressing teen metamorphosis, that nervy, in-between energy turned out to speak by proxy to larger shifts, such as the post-war schism of tradition and consumerism; nuclear-age existential vertigo; tensions between the sexes or among black, white, and brown in America; and much more.

However, rock had trouble assimilating the next big transitional point in most people’s development—the different kind of awkwardness of middle age. As Mick Jagger guessed in 1966, “What a drag it is getting old.” At least for a while. As it’s turned out, rock-era figures are OK at becoming seniors—Dylan, Neil Young, Paul McCartney, Stevie Nicks, David Bowie, and many other icons wear their silvering hair with élan. The painful part came earlier, in the 1980s, when those stars hit their 40s and began to resemble the parents they once seemed born to vex.

Young, Joni Mitchell, the Grateful Dead, Bowie, Bruce Springsteen, the Who, Van Morrison, of course Dylan, and even the Clash—almost no Boomer icons escaped being tarred as sellouts and has-beens in the 1980s, often by critics barely a few years younger who expected rock gods to be exempt from time’s scythe. Today, I think, we are beyond that fantasy and project less shame onto aging artists, which makes them less prone to wriggle into self-conscious updates as if they were unflatteringly tight shirts.

Beyond rock’s internal growing pains, though, the ’80s were a time of cultural counterrevolution, led by stock brokers, family-values preachers, and the Reagan White House, demanding the total liberation of the market and the re-regulation of private life. Liberal millionaire celebrities didn’t fit on any side: They weren’t down with the agenda, but they were fat cats still. A new globalized order was emerging—the one we’re still living with—and the utopian platitudes of their youth didn’t have much to say about it.

Yet 1980s critics still expected rock to be about resistance, and rock was letting them down, Dylan maybe most of all. Which is silly, ultimately, because aside from his brief bouts of true-believer fervor for civil rights or for Jesus (and often even then), Dylan always keeps on doing the only thing he’s built to do, which is to mulch all incoming data into symbol, rhetoric, jape, and patter. In the 21st century, he’s applauded for it again, but in the 1980s his audience wanted more, and Bob Dylan’s never really taken requests—ask him for a shovel and he’ll give you an armadillo, shrugging, “Look, man, they both dig.”

And this is where the Bob Dylan in the 80s project whiffs: Mostly it just hands us the shovel. To show that these are good rock songs, it presents them as good rock songs. Which is fine at first but adds little to the originals. Aside from Finn, slipping by on sheer charisma, the exception is musical clown Reggie Watts’ version of “Brownsville Girl,” Dylan’s 11-minute ramble co-written with Sam Shepard from 1986’s Knocked Out Loaded—Watts turns it into a four-minute chunk of lovers-rock reggae, mainly singing the chorus but also rolling random lyrics around his mouth with his supple lolling tongue.*

Since one thing Dylan’s never had the pipes to do is to sing very prettily, I’m also taken with a couple of the ballads—Dawn Landes and Bonnie Prince Billy’s duet on “Dark Eyes” and My Morning Jacket guitarist Carl Broemel’s rendition of “Death Is Not the End.” Otherwise most of these versions simply seem like rote payments of respect, with the singers sounding pseudo-Dylanish, the way other actors often seem like they’re doing Woody Allen imitations when they’re in his movies.

Once the point’s been made, why listen to a bunch of competent knockoffs when I can go back and hear Dylan himself delivering the songs with all his own messy, wrecked, cobwebbed, missing-person, bottomless-pit mystery? At least then they’re part of a suspense drama in progress, not a toast at a commemorative banquet.

If you are looking for a record that freshens up some of Dylan’s music from that era, seek out Gotta Serve Somebody from 2003, on which black gospel singers perform his born-again numbers. It hints that maybe proselytization wasn’t motivating him so much as the urge to leave his mark on yet another of America’s best musical traditions. (I’m also looking forward to Light in the Attic Records’ coming reissue of 1969’s Dylan’s Gospel, where his 1960s standards are given the salvation treatment by the California collective The Brothers & Sisters, including Merry Clayton, whom you may know from the Oscar-winning doc 20 Feet From Stardom.)

Bob Dylan in the 80s is tagged Vol. 1, but if there’s going to be a sequel, let it be a ménage of artists from varied genres, with a mandate to rip the tunes up and patch them into cockamamie alien designs. Dylan notoriously does that to his songs in concert, and he’s done it to his identity and role in the culture decade after decade, even when it’s garnered him only grief. As the old coot himself might drawl, “C’mon, honey, give a real tug on that skinny necktie.”

Correction, April 2, 2014: This article originally misspelled the last name of Sam Shepard. (Return.)