Sometimes, flicking through the online Neil Young Archives, one wonders if he has slightly oversold the marvels on offer for public perusal. In his introductory video, Young guides new users around the site, showing them the audio, video and documentary material on offer. “Here we have a copyright letter,” he intones, over footage of an envelope. “Very interesting!”

One hopes Young is being ironic, despite not having a reputation for being among music’s great comedians, because Neil Young Archives offers rather more interest than the chance to ponder his copyright affairs in years past. After a free introductory period, it has now become a subscription service – at $1.99 a month, or $19.99 a year – but until then you can poke around all you like. Even once you have to pay to enter, those rates are hardly extortionate given that you get access to everything he’s released, a load of unreleased music, and supporting audio, video clips, press clippings, documentation and memorabilia. It’s everything to do with Neil Young in one place.

Perhaps Archives will prove to be a damp squib, despite Young’s additional promise that all his new music – brand-new, previously unreleased archive material – “will always be heard there first”. After all, Young has form in making confounding decisions about the best way to present his music: the original Archives box set, which was available in a DVD edition so hard to navigate that it left the Guardian’s Alexis Petridis – a Young obsessive – “howling for the luddite comforts of a CD box set with a nicely illustrated booklet”. Then there was Pono, the music service launched upon a world that Young believed was eager for master-quality audio just as the world actually decided, you know what, crappy phone sound is perfectly good enough for music.

One-trick Pono ... Neil Young’s ill-fated, high-end portable music player. Photograph: Franz Krachtus/AP

Neil Young Archives feels different, though. Young’s grand gestures have previously appeared to be designed with the intention of pleasing only Neil Young – and Neil Young in one of his most spectacularly ornery moods – but this feels aimed at the fan. Not the fan who’s willing to mortgage their house in order to buy a nine-disc box set, or the fan who actually believes that music only sounds good when played at master quality, but the fan who just wants to track the trajectory of Young’s career and increase their understanding of it. Even a fairweather fan like me can lose the best part of the day chasing Young’s rabbits down their holes. Perhaps this might be the way forward for legacy artists: the first groundbreaking yoking of technology to archival content in more than 30 years.

The first wave of legacy reappraisal was driven by the combination of economics and technology. On the one hand, compact discs offered the opportunity to fit almost 80 minutes of music on to a single disc – which meant you could offer several hours of music in a package that wouldn’t cause your arms to fall off when you carried it home. On the other hand, the baby boomers who were thriving in the mid-80s didn’t balk at the prices the labels were demanding for the new format.

The first major artist to note the opportunity to both reel in the dollars and offer the fans an insight into their past was Bob Dylan, who released the 3CD/5LP set Biograph in November 1985. It was an imperfect but worthwhile release – 16 unreleased tracks, a handful of rare single-only releases, and an assortment of album tracks that were as often baffling as they were sublime. In his review for Creem, John Mendelsohn noted: “I’m not so sure that anyone’s going to feel that his or her favourite Dylan is adequately represented on Biograph, which may have been programmed by monkeys on sabbatical from trying to type the complete works of Shakespeare.”

Perhaps the moment at which the possibilities of the box set were fully realised came with Eric Clapton’s Crossroads in 1988, the first box to go platinum in the US. This was a set that did what Biograph had promised, spanning a whole career from the Yardbirds onwards, with the unreleased and alternate cuts complementing the greatest hits. It was, said David Fricke in Rolling Stone, “a piece of primo rock & roll detective work”, offering value to casual fans and diehards.

‘Imperfect but worthwhile’ ... Bob Dylan pictured in 1985, the year he released box set Biograph. Photograph: Dave Hogan/Getty Images

It wasn’t hard to see the appeal of Crossroads for Clapton fans, and it became the model for subsequent boxes. And, for a while, it felt like living in an age heaven-sent for music fans. No one bats an eyelid at galleries charging £20 for the chance to spend an hour looking at an artist’s preparatory sketches, or seldom-seen work, and box sets fulfilled the same function for music fans, but with the major work in the same exhibition. Throw in a good booklet and a top-quality box could be revelatory. In the early 90s, I was snapping up this stuff, as a great way of a quick deep-dive, compelled by both the hits and the obscurities: the Beach Boys’ Good Vibrations box with a whole half-hour of unheard Smile material, the 1990 Byrds box with the unheard Gram Parsons vocals, the Velvet Underground’s Peel Slowly and See, on which the version of Ocean is still my favourite of all VU recordings.

At that point, box sets had value precisely because they were unusual. They didn’t stay unusual for long. By the mid-90s, boxes were flooding the reissue market. A decade later, and pretty much anything that could be compiled would get a box – artist, genre, label, you name it. We’re now at a point where boxes have become so hyper-specialised as to exclude casual listeners. One recent release is advertised with the selling point – and this is true – of containing an unreleased Cud demo. Even the major artists became obsessed with obscuring wood with trees: Dylan’s bootleg series started with a series of releases that were essential to anyone with an interest in rock history; by the time you reach an 18-disc collection of every note he recorded in 1965 and 1966, it’s hard to know who, really, is supposed to listen to and appreciate it all, even among the “Bobcats”.

But even in the early 90s, there were legacy artists who perhaps foresaw the dead end boxes would prove to be, and who looked to other ways to serve the needs of their fans. The Grateful Dead, who built their bond with their fans in the live setting, began putting out the From the Vault and then the Dick’s Picks CDs, allowing fans to hunt out shows they wanted to hear. As the internet became the predominant mode of music distribution, others copied the Dead, making shows available through their websites. Pearl Jam, by making every show available, have sold 3.5m “official bootlegs”. Springsteen fans can hunt out historically significant shows on his website, as well as the current performances he has started to make available.

‘A bloody-minded determination to do what he wants’ ... Young in Amsterdam, 1974. Photograph: Gijsbert Hanekroot/Redferns

Still, though, this wasn’t the best new way of presenting and preserving a legacy. Live shows tended to come shorn of context; the CDs or downloads did not come with sleevenotes. You might be able to find it yourself – reading Springsteen fansites and messageboards gave me the insight I needed to decide which live shows to buy from his site – but once the music was yours, that was all it was: music. Perhaps the single best argument in favour of keeping your CDs is the inlay card, especially for reissues, which might have a decent essay in them. Rely on streaming services and you won’t even know who the songwriters are, or the producer. And that stuff matters, because it’s what sends you off on a mission to discover other music. The context provides the connections, the proof that this stuff does not all exist in a vacuum, and is part of a wider musical world that deserves investigation. It helps you join the dots: it’s from reading sleevenotes I realised the same man, Speedy Keen, had written the Who’s Armenia City in the Sky, Thunderclap Newman’s Something in the Air, and produced Motörhead’s self-titled single. I would not have learned that from Spotify.

And that’s why Neil Young Archives feels like a breakthrough. Here at last is an online presentation of an artist’s catalogue that presents the hits and the rarities, alongside all the relevant information about every track – the lineup, the location, the producer, where it was released, plus supporting documents, photos. It’s like one of the first wave of box sets expanded to its logical extreme, but still – despite its huge breadth – manageable in a way that the 18 CDs of Dylan’s The Cutting Edge just weren’t. You can concentrate on individual albums, or on periods of work; you can compare the solo work with the Crosby, Stills, Nash and Young music from the same time. You can listen to study, or for pure pleasure.

Of course, Neil Young has certain key advantages over other artists that have enabled him to do this: a fascination with the possibilities of technology, a bloody-minded determination to do what he wants, and the clout to get it done. But flicking through Neil Young Archives, the possibilities for other artists beam out like headlamps. Here’s the future, albeit the future of the past.