What is the first Bob Dylan album everyone should start with?
With 40 studio albums, 21 live albums and 17 volumes of his gigantic Bootleg series, the well of Bob Dylan goes deep. For a first timer, staring over the edge, it’s an intimidating prospect to even consider jumping in. It’s better to drop a bucket in and fish tasters out, album by album, but even still – where do you begin?
Each and every Dylan fan will give you a different answer here. There will be fans who claim the only place to start is with some niche Bootleg section where he’s trying and failing to get the right wording through ten different studio outtakes. Others will try and trick you into starting with his latest work – do not fall for that.
It comes down to the question of what’s the point? Is the point of beginning to listen to Dylan merely to respect a musical legend or to appreciate his position in the history and lineage of folk and rock? Or is it to get excited and to be motivated to then dive deeper, listen more and eventually, become a self-proclaimed fan?
Either way, my suggestion would be to get back to the beginning. Surely no one out there would first hear a croaking 1990s Dylan singing ‘Wiggle Wiggle’ and be left hungry for more. Also, by the time he hits his spiritual era in the late 1970s and early ‘80s, that too can become alienating for those not quite as indoctrinated in faith.
But back at the start of it all, Dylan is not only more enjoyable and accessible, but there’s also a clearer understanding of who he is and what makes him tick. As he was releasing records in quick succession, there’s a sense that you can even track his feelings through his work, being able to grasp where he was at in terms of his love life or sense of belonging, or especially where he was at in terms of his own career and feelings towards his newfound fame.
You could definitely start at start with the 1962 self-titled debut, but as it’s packed with mostly covers, it doesn’t teach much about the start. In that sense, The Freewheelin’ Bob Dylan feels more like his debut and would definitely be a good place to begin for folk fans finally ready to discover the master.
However, if you’re hear to take the advice of someone else, start with 1965’s Bringing It All Back Home. 1965 was a year of flux for Dylan. He was done sick of the folk scene, sick of protest music, but when he recorded this record in January, he’d get to pick up the electric guitar and use it like an axe. So instead, you get the best of both, powered by the passion of frustration.
This feels like an electric Dylan album purely because of the energy running through it. Suddenly, he has a full band backing him up, meaning that a spanning track like ‘Bob Dylan’s 115th Dream’ is no longer the simple brother to 1963’s ‘Bob Dylan’s Dream’, but is a far bigger production.
It also led to tracks like ‘Subterranean Homesick Blues’, where elements of blues and rock are floating in. Joining up with his signature social commentary, this moment feels like a meeting of two worlds. It’s the fault line between Dylan the protest folk star and Dylan the rockstar, where for a glorious moment, he was both.
But for first-timers keen to get started with Dylan, there is some purism here. On side two, or the acoustic side, things are simple. Just the man and his guitar, tracks like ‘It’s All Over Now, Baby Blue’ and the incredible ‘It’s Alright, Ma (I’m Only Bleeding)’ are as reflective of his folk as any track from any older album.
The perfect balance between simple and exciting, poetic and hooky, old and new – you can learn almost everything about 1960s Dylan on this one record, so why not just start there?
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