In 1992, no one wanted to hear organ on a rock song. At least that’s how Jakob Dylan, pragmatic frontman of the Wallflowers, explained the mediocre sales figures for his band’s self-titled debut. Those warbling, metallic emanations from Rami Jaffee’s Hammond B3 twisted through their scrappy first album like the double helix of a DNA strand, or miles of winding railway track. The record came out roughly one year after Nirvana’s Nevermind, which landed like a warhead and rearranged the molecules of rock music for the next two decades. To his label’s dismay, Dylan’s shambly bar-band melodies did not capture the rage—or the allowances—of American teenagers. But then, he never set out to be the voice of a generation.

Jakob Dylan formed the Wallflowers in a fit of surrender. Whether it was conscious or not, he’d been resisting the family business for years; many men outdo their fathers, but only a fool would think he could best Bob Dylan. So he didn’t try. When pressed about his childhood in early interviews, the younger Dylan alluded to a whitebread American upbringing. As a kid, he played Little League. He idolized his older brothers, who exposed him to all kinds of punk rock: the Jam, Stiff Little Fingers, and crucially, the Clash. That charged music ignited something in Dylan, who picked up a guitar as a pre-teen, and played in garage bands with names like Trash Matinee.

He had tried to conceal his lineage for as long as humanly possible. In school, there was nowhere to bury it, but Dylan would hide out when he could. One day in seventh grade, his classmates flipped their social-studies textbooks to a chapter about the 1960s. Printed on a page next to Martin Luther King Jr. and the Beatles was a thumbnail photo of Jakob’s dad. He asked for a bathroom key and slipped quietly out of the classroom. After high school, Dylan moved to New York to study painting at Parsons. It was one final push against a tide rising inside him. Two weeks into the semester, he returned to Los Angeles and accepted his fate.

Dylan enlisted his childhood friend Tobi Miller on lead guitar, bassist Barrie Maguire, and drummer Peter Yanowitz, who gigged in the late ’80s as the Apples, “which is even more pathetic than the Wallflowers,” the frontman once joked. Jaffee joined two years later, as the band became more of a presence around L.A. They convened in the back bar of Canter’s Deli for weekly jam sessions, where Jaffee invited scores of local musicians to bang out Neil Young covers around a beat-up house piano. Jaffee played with Dylan daily for about two months before Yanowitz tipped him off about his old man.

By the mid-’90s, the Wallflowers’ debut had only moved 40,000 units. Maybe it was the organ. Maybe the vocals were too muddied in the mix. Or maybe, to entertain another of Dylan’s pet theories, it wasn’t sad, angry, or grunge enough. “It’s just not what I’m interested in,” Dylan told The Los Angeles Times when asked if he’d consider a heavier sound. “I was never interested in just being in fashion. I was never the kid on Melrose who wanted to grow the dreadlocks and put on Doc Martens.” The limp reception prompted a change in labels and personnel—only Jaffee stayed on with Dylan as they readied their second album, 1996’s Bringing Down the Horse.

“When our contract fell through, there was a year where nobody would come to see us, talk to us, or even return our manager’s phone calls,” Dylan once told Billboard of his band’s post-debut slump. “We were severely damaged and mauled goods at that point.” That stale sense of dissatisfaction crept into the songs on Bringing Down the Horse, which Dylan wrote in the fallow years between 1992 and 1996. The title, a tweaked lyric from the forlorn “Invisible City,” referred to Dylan wresting control of his own creativity. For the Wallflowers’ second album, Dylan and Jaffee were joined by guitarist Michael Ward, drummer Mario Calire, bassist Greg Richling, and vitally, producer T Bone Burnett, who’d sculpted sounds by Elvis Costello, Marshall Crenshaw, Bruce Cockburn, and Gillian Welch. Burnett had also known Jakob since he was a little boy, when he manned piano and guitar in Bob Dylan’s Rolling Thunder Revue.

More than an adept, sensitive producer, Burnett was a kindred spirit to the Wallflowers. His own solo career was steeped in murky Americana. A sly observer and incisive commentator, Burnett would cut one record as a roots traditionalist and cram his next session with a drum kit, harmonium, and a string section. For Bringing Down the Horse, Burnett split the difference and mostly stuck to the Wallflowers’ core instruments, giving them some separation and clarity. Unlike their scruffy debut, which was recorded live, Bringing Down the Horse was warm and precise. Jaffee’s organ melodies, whirring out of a B3 and a Vox Continental, were a defining element of that sound.

Dylan had spent the past three years trying to sharpen his writing, almost as a defensive strategy. Comparisons to his dad were crowding the columns of every interview; it was the rasp and slight whine in his voice. His deft, painterly verses. The fact that he dared to make rock music at all. “I can’t imagine a more daunting specter to have for a father, especially if you’re a singer and a songwriter,” Burnett told The Los Angeles Times several months after Bringing Down the Horse hit the shelves. Despite everything it afforded him, Dylan hauled his surname around like an albatross. There would always be a sect who saw their prophet’s son as an unskilled leech.

Though he wouldn’t discuss song lyrics at length, Dylan admitted that “Bleeders,” one of the best cuts on Bringing Down the Horse, was a dissection of all that judgment. As the song crept in on spangled guitar and a liquid line from Jaffee, Dylan compared his conflict to a fish fighting against the current.

Once upon a time
They called me the bleeder
Swimming up this river
With sentimental fever

But this ain’t my first ride
It ain’t my last try
Just got to keep moving on
If they catch me ever
They’ll throw me back forever

Dylan would later admit that “sentimental fever” referred to the devotion to songwriting he’d inherited from his father. Those hands, plunging into the water to disrupt his upstream struggle, belonged to the record industry. “[I was] being told countless times that I was not very good, and that the songs were no good, the band was no good, and that there was no future to this thing,” Dylan told Details in 1997, elaborating on the origin of “Bleeders.” “There was a time there when it was embarrassing to say the Wallflowers were playing.” But the numbers were reflecting a different narrative.

Bringing Down the Horse was climbing the charts, and by the close of 1996, it had reached No. 74 on the Billboard 200— wedged unceremoniously between MTV Party to Go Vol. 10 and ESPN Presents: Jock Jams Vol. 1. The album front-loaded its two biggest singles: the keening ballad “6th Avenue Heartache,” and the moody alt-anthem “One Headlight.” Dylan had written the former during his stint in New York, where he watched an older unhoused man play Everly Brothers songs on the steps of an apartment building daily. One morning, the man was gone, and people pilfered his belongings bit by bit.

The production of “6th Avenue Heartache” is some of the cleanest and most calculated on Bringing Down the Horse. To complement Jaffee’s rippling chords, the band brought in Leo LeBlanc, a pedal steel guitarist known for his work with John Prine. Dylan’s melody, a heartsick country dirge, was near-perfect. But then someone brought in Adam Duritz. The Counting Crows frontman, with his treacly, Glee Club pipes, spoils Dylan’s effortless rasp. Duritz dates the song, and his presence almost feels like a cash grab. “Maybe you don’t think you will like the album because I’m on it, but hey, Adam Duritz is on it also,” Dylan joked with Billboard about the single. As a business maneuver, it was shrewd: Counting Crows were a multi-platinum property.

Because Dylan is a talented songwriter, his misses feel more lazy than overwrought. Sleeper tracks like “Three Marlenas” and “Angel on My Bike” bob atop stagnant, circular melodies, like ice diluting a drink. Lyrically, Dylan does little to spike the tepid punchbowl; “Angel on My Bike” features a string of dull and undetailed passages, like this one:

I can’t handle a care
I want, but I can’t be there
While angel’s a prayer

It’s 45 miles on that highway
Angel double prayer

Throughout the song, Dylan’s rhyme schemes are unimaginative, his vernacular feels limited, and there is hardly any concrete imagery to chew on. In one exception, he sketches a nautical quagmire worthy of scrimshaw: “She found me down on a two-ton anchor/Tangled up in wire.” It’s a brief reminder that Dylan’s poetic strengths lie in specific renderings of American masculinity—ill-fated sailors and wanderers, brined by the sea or cured in cigarette smoke.

“Three Marlenas,” “Josephine,” and cringey bar-rocker “God Don’t Make Lonely Girls,” present another thematic suite on Bringing Down the Horse, with Dylan tightening his scope on the opposite sex. He watches one woman dance “behind the glass at a peep show,” and trails another as she recovers from a one-night stand. “Josephine,” a modest but piercing ballad, centers on someone with a “schoolgirl smile,” who presumably tastes like “sugar and tangerines,” as Dylan muses over warm, gold-toned guitar. Whether he is recalling a childhood love, or writing from the perspective of a ’90s Humbert Humbert, I cannot say.

What connects these three cuts is an innate (though likely unintended) sense of moral superiority over sexually liberated women, or at the very least, a fixation on purity. On the drowsy “Three Marlenas,” Dylan’s language is sparse but seemingly loaded with judgment. A distressed damsel with lipstick-smeared clothing lies alone in “somebody’s” bed, indicating a screw that didn’t offer foreplay, or even a first name. “She only went and did what she did/’Cause he would drive her home then,” Dylan sings in the first verse, his vocal chords sputtering at the close of each line. His refusal to name exactly what “she did” smacks of an unspeakable act. That she leveraged sex transactionally—for a ride—seems clouded with misplaced pity.

The most garish of this conceptual trio is “God Don’t Make Lonely Girls,” which treats its leading lady like some honky-tonk “Roxanne.” Dylan plays the peep-show patron, who projects his wholesome fantasies onto the dancer before him. “Something is wrong, she don’t belong,” he drawls, his bandmates summoning the swagger and twang of a Ford commercial. Much like Sting’s sex worker savior, Dylan’s character fancies himself a shining knight who can solve the dancer’s problems with a mere wardrobe change. “I’ll bet she’d look good in a brand new dress/She never felt good in her fishnet,” he assumes, a bit too pleased with the thought. The song reeks of feel-good filler—like something that you might hear at a county fair. But its Puritan gender framing dates the album more than anything else. No wonder the Wallflowers front-loaded their strongest work.

If you watched MTV in the ’90s, you need no introduction to “One Headlight.” The music video was coursing through the cable TV circuit like an ice cream truck circling the suburbs. Like much of the album, the song was structurally simple—a canvas for Dylan’s rust-eaten imagery: cheap wine, busted trucks, and the stench of death. For all the media’s insistence that Dylan must have been influenced by his dad, “One Headlight” pointed to another American Son: Bruce Springsteen. The lyric “This place is old/It feels just like a beat-up truck/I turn the engine but the engine doesn’t turn” was a direct reference to Springsteen’s 1987 song “One Step Up”: “Went out and hopped in my old Ford/Hit the engine but she ain’t turnin’.” Dylan accepted the irony that even if he didn’t spin his father’s records till the grooves smoothed out, his idols surely had.

At some point during the promo cycle for Bringing Down the Horse, someone remembered a powerful economic force: schoolgirls. I was only 7 when the shadowy video for “One Headlight” hit MTV, but it was obvious that Dylan had been packaged as a heartthrob. Shot under a bridge in Brooklyn, the visual pulls tight focus on Dylan’s eyes, which have been labeled every shade of azure since the clip first aired in 1997. His fetishized irises seemed like a marketing course correction: The video for “6th Avenue Heartache,” directed by a young David Fincher, had all the allure of a PowerPoint presentation. It was also filmed in black and white, robbed of those “startling, Samoyed-blue eyes,” as one reporter described them. The rest of the album’s videos were shot in color.

Dylan was aware of his hunk status, but didn’t dwell on it too much. He was a husband and father in his mid-20s, and had seen first-hand how fame could corrode family life. If his picture was being torn out of glossy magazines and slipped into binder covers, he found it amusing. In a 1998 interview with Rolling Stone, the wry musician was asked to comment on his undeniable “yumminess.” “Well, you know, to be called yummy is a fantastic honor,” he said, tongue firmly in cheek. “I’m going to do everything I can to continue to face up to that and not let anyone down in the future.”

But while he laughed at himself and his perceived sex appeal, Dylan never dismissed the contingent of Wallflowers fans who were taping his photo on their bedroom walls. “People frown on having young fans, especially young girls,” he said in ’97. “But if people look back and get their education, they’d realize young girls discovered the Beatles before anybody.” Dylan was quick to clarify that he wasn’t ranking his band alongside the Fab Four—but he couldn’t ignore the frenzied concertgoers. One night at Boston’s Avalon Ballroom, a frilly brassiere made its way on stage, followed by a dog-eared copy of Lolita.

By 1998, Bringing Down the Horse had sold 4 million copies—more than any solo studio album by Bob Dylan, as the trade papers liked to point out. “One Headlight” picked up two Grammy Awards that year, for Best Rock Song and Best Rock Performance by a Duo or Group. The Wallflowers would go on to release five more studio albums; their latest landed just two years ago. But they’d never summit the mountain again. Arriving between the death of Kurt Cobain and the release of Radiohead’s OK Computer, Bringing Down the Horse was the last gasp of chart-topping, Western-bent alternative rock. Dylan was no longer swimming upstream. And the hands that had tried to grab him were fishing in different waters.

Additional research by Deirdre McCabe Nolan

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The Wallflowers: Bringing Down the Horse