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It’s hard to pinpoint exactly where the Wallflowers live. The project is controlled and helmed by Jakob Dylan — son of Bob, but you knew that — and may have always been destined for a conflicted identity. The Wallflowers have been slotted into that weird position of being a classicist rock band that just more or less plugs along despite whatever trends or currents are moving around it. That aesthetic had its mainstream moment in the band’s ’90s heyday, but even then it was an out-of-time option for those who didn’t see themselves in the heavy angst of the Alt Nation explosion of the earlier ’90s. The Wallflowers weren’t a part of some major movement that acted as salve or reaction to that; they weren’t the harbingers of the next trend in rock music that would change course. (I’m not sure that a landscape filled with dozens of lesser Wallflowers attaining major success in the late ’90s would’ve been a great thing, per se, but an alternate history where things swung this way instead of the death-spiral of post-grunge and nu-metal has its appeal.) At the same time as all that, the Wallflowers, for a moment, became a massive band when they released Bringing Down The Horse, which turns 20 tomorrow. It was the reboot and the breakthrough, an album that yielded a couple definitive ’90s hits, of the quality and ubiquity that means the band may also always be tied to this specific moment in pop culture history.

This is based on anecdotal evidence from my own conversations, but it feels as if Bringing Down The Horse is often be mis-remembered as the Wallflowers’ debut. In reality, the roots of the band go back to the late ’80s, and their actual debut was 1992’s self-titled LP, released on Virgin. That album struggled commercially, and the Wallflowers soon parted ways with Virgin, reportedly on mutual terms. Four years later, they returned with Bringing Down The Horse — or rather, Jakob Dylan returned. The lineup had shifted, years had passed, there was a new deal with Interscope. There was also a different clarity of vision, a different muscularity, and songwriting that displayed plain confidence that Dylan had figured this one out better than the last.

Bringing Down The Horse was eventually certified quadruple-platinum by the RIAA, meaning it had shifted four million units. While that number is tiny compared to generational totems like Nevermind or Ten, it’s still the mark of a very, very big album. But what most people still remember the album for are the twin hit singles “6th Avenue Heartache” and “One Headlight,” and — perhaps to a lesser extent these days — “The Difference” and “Three Marlenas.” The former two, especially, were the kinds of songs that you heard everywhere at the time, and that you continued to hear everywhere pretty much every year since they were released. Randomly on the radio, randomly in restaurants, randomly in the shopping mall — “One Headlight” and “6th Avenue Heartache” were universal rock hits on the scale that rock bands would soon no longer be able to attain very frequently. This is something Dylan acknowledges and expresses gratitude for; he regards even having those couple of major songs as something of a gift. And he isn’t wrong — plenty of bands would love to have songs with that reach. But even so, the shadow of those songs is another shadow in a career that was defined by one.

I can’t wrap my head around what it must be like to have a father like John Lennon or Bob Dylan, and to harbor your own ambitions to be a musician. Is it like, “Well, my dad does this, so I’ll give it a shot, too?” as if you’re taking over the family business? Jakob, for his part, never hid from the fact that he had a massively influential and famous father. But he also never talked about it for a very long time. Over the years this fueled speculation that Jakob and Bob did not have a good relationship, but Jakob has refuted this and has discussed the fact that he wanted to make an earnest attempt at being taken on his own terms. Jakob’s parentage has loomed over his entire career, so this isn’t intended to belabor the point or return to thoroughly-visited ground — but the interesting thing about the Wallflowers existing within the shadow of Bob Dylan is just how much of a different kind of star Jakob Dylan became upon the release of Bringing Down The Horse. Jakob Dylan was a sex symbol and a modern-rock radio fixture in the big-budget CD era. He was not an oddball folk troubadour that everyone was trying to catch. He was like a more palatable descendent: better-looking, with a more conventionally appealing voice, a sleek modern swagger. Bob Dylan had a tendency to write a generation-defining song every year for a decade or so, but often worked in a strain that now feels woven into the history of the 20th century and before and beyond; Jakob Dylan wrote direct pop songs for a distinct slice of his era. They were two men linked by blood and coming from similar traditions, but they wielded what they had in different ways and in different contexts. It’s an impossible standard to live up to, having a father who’s become a part of American lore. But the curiosity of a Dylan still steeped in classic rock tradition while also becoming a heartthrob in an era when MTV mattered is one facet of American rock history I’ll always find fascinating.

As a songwriter, however, Jakob Dylan had more to do with Bruce Springsteen — check the gravel in his inflections through the verses of “Three Marlenas” — or Tom Petty. (As it happens, the Heartbreakers’ Mike Campbell was responsible for that slide guitar part in “6th Avenue Heartache.”) It’s something Jakob has talked about in hindsight, acknowledging the traditionalism of his band, but also the scope he was trying to get from looking backwards. “I was ambitious…but I wasn’t looking to fit in anywhere,” he told American Songwriter in 2012. “I wasn’t trying to write anthemic, angst-ridden songs at that time in the mid-’90s. That wasn’t really ever my calling.” (In an interview with Consequence Of Sound from the same year, he said it in a slightly less inspiring way: “Being interesting, or inventive, or any of that kind of stuff, I’d rather just sit back and watch lots of other people chase that tail.”) The other part of that American Songwriter quote has Dylan citing the “big, epic songs” his heroes were writing, and that he was chasing that same sensibility. On Bringing Down The Horse, you can hear Springsteen-esque swells of highway drama in “One Headlight” and “6th Avenue Heartache” and “Angel On My Bike.” The sprawling slower songs like “Josephine” or “I Wish I Felt Nothing” might not rise to some “Thunder Road” crescendo, but they have the layered, enveloping atmosphere of that brand of ’70s epic. Even so, it’s an issue of perception. This was a young songwriter descended, biologically, from the guy many pop fans would argue was the greatest American songwriter of the century. That is a heavy challenge for a new artist to counter.

I can’t help but feel like that influences the tone and feel of Bringing Down The Horse. Jakob Dylan had to exist in that shadow of his father, and his first attempt at that hadn’t worked. Even without the pressure of being “Bob Dylan’s kid,” his debut hadn’t ignited. He had to get a new label. He had to start over right after he’d gotten in the door. The result is that there’s a sense of weariness and defeat hanging over Bringing Down The Horse. Dylan was 26 when it came out, but he sounds like a much older man. Part of that was his ever-present power-rasp, part of that was the languidly ragged sounds that permeated the album. But he was channeling all of that into something accomplished, not something that actually sounded defeated. Bringing Down The Horse just sounds like the name of a classic album, and in the sense of the ’90s, Dylan pretty much achieved that, even if the band’s legacy has not proven to be one of a classic band. It’s an album made by a young artist digging in his heels in the face of pressures and failures, and trying to make something timeless. And you can hear that effort in the music itself.

On the other hand, Dylan also didn’t want to make something that was just a cheap bit of ’60s/’70s revivalism. He hired certain people to make it a current-sounding record, and it does sound ’90s in a way that, today, you can’t really separate it from the decade. It’s not one of those contemporary rock albums that literally sounds like it could’ve existed in past decades — à la, say, Fleet Foxes or the Strokes. Bringing Down The Horse is too crisp; even if it’s lived-in compared to the work of the band’s peers, you could imagine how much more weathered these songs would sound had they been released in the ’70s. And that’s if you’re ignoring the fact that there’s something ineffably ’90s about the vocal melodies Dylan favors. Even if he makes a lot of noise about always having been interested in Americana and folk traditions (and producer T Bone Burnett calling Bringing Down The Horse a “hyper-modern folk record”), the way that gets filtered through Jakob Dylan makes sense for the guy we’d see in those music videos. It makes sense for MTV. It makes sense for the ideal of modern rock radio of the ’90s. And it didn’t hurt that rising roots-rock star Adam Duritz (of Counting Crows) delivered some distinctive background vocals on the album’s first single.

There are moments that are so cripplingly ’90s, like the David Fincher-directed “6th Avenue Heartache” video — that stop-start blurred motion video trick that was all the rage for a moment that decade. But it’s not a version of the ’90s we think about much anymore, in this era where so many rock bands quote scuzzier versions of grunge, or ’90s indie, or late-’90s emo. It might not have been a version of the ’90s that ever really existed, or at least it could be one that’s blurred by nostalgia if you were of a certain age when Bringing Down The Horse came out. Ultimately, it’s an album that didn’t sound of its time in the most obvious ways, but is also inseparable from the ’90s — these songs are etched into memories of that time, whether they’re nonsense or tangible.

And a not-insignificant factor in Bringing Down The Horse feeling inextricably ’90s is that the Wallflowers never touched this kind of success again. They are forever of that decade. It would be another four years before the Wallflowers released the followup to Bringing Down The Horse. When its successor, Breach, finally arrived in 2000, it hardly hit gold status. That’s still an accomplishment many rock bands would look at as fantasy today, but not when following an album that went quadruple-platinum. In those times, and for a band that had the stratospheric success of the Wallflowers, that was a severe commercial downslide, and it was one that continued over the course of their next several albums before the group went on hiatus in the mid-’00s. For some, they may live on as a small-scale legacy artist. Dylan is still a good songwriter, he comes from a royal rock lineage (and didn’t embarrass himself or come across as a nepotistic extension of that lineage). To others, Bringing Down The Horse is an artifact of its time — a time that happened to allow for the fluke event of Bob Dylan’s son showing up, somehow making a 4x platinum album, and then gradually sliding into relative obscurity.

Those are the circumstances that will always hang over this record, and will probably always hang over Jakob Dylan. But much of the Wallflowers’ work deserves better — especially Bringing Down The Horse. It’s an album of humid summer nights spiraling out in no direction in particular, of listless walks and drives to the somewhere else that yearning rock music always seems to promise. (That’s another way in which Dylan’s work here followed more in Springsteen’s footsteps than it did his father’s — Bob Dylan might be the symbol of escaping and re-making yourself in America, but does his music ever promise that the way Springsteen’s does?) It captures the aimlessness and frustration of youth when not only trying to figure out your place in the world, but also trying to make something great. That’s what can make for eternal rock music, and despite the ways in which the Wallflowers can feel so definitively of the ’90s and their surroundings, that’s something they had the prowess to pull off at least once, with Bringing Down The Horse. Radio success or lightning-in-a-bottle moments aside, that’s what makes an album enduring.