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Where to Start with Bob Dylan

Mike Grindle is a freelance culture writer with a love for film, music, and literature.

Bob Dylan's self-titled 1962 debut

Bob Dylan's self-titled 1962 debut

With a career spanning more than 60 years and 39 albums to his name, there's no doubt that any new fan of Bob Dylan will find themselves with plenty of music to explore. But they may also find themselves quite at a loss as to where they should begin.

Amongst Dylan's vast discography, there have been ups and downs, comebacks, iconic hits, hidden gems, and multiple changes in musical direction. The 60s alone would see Dylan go from protest singer to rock star to country musician. Further complicating matters for the newcomer is the fact that some of Dylan's most celebrated works are not necessarily his most accessible.

This article will guide you through your first encounters with the legendary folk singer-songwriter so you can explore his discography with relative ease.

"Bringing It All Back Home," 1965

"Bringing It All Back Home," 1965

Start Here: Bringing It All Back Home

Though commercially successful and critically applauded, Bringing It All Back Home may seem like an odd choice for your first foray into Dylan's discography. But while it may not be his magnum opus (it depends on who you ask), it's a highly accessible entry point. Also, the album catches Dylan at a juncture between his two most celebrated eras: that of his folk-singer days and the more rock-oriented masterpieces. As such, you get a taste of the best of both worlds.

Fun Fact: The woman on the album's front cover is not a former girlfriend of Dylan, but his manager's wife, Sally Grossman.

"Highway 61 Revisited," 1965

"Highway 61 Revisited," 1965

2nd Choice: Highway 61 Revisited

Dylan may have embraced a more rock-band style in Bringing It All Back Home, but with Highway 61 Revisited, he truly "plugged in" and changed music history. Beginning with the hit, "Like A Rolling Stone," Highway 61 Revisited is one of those album where every song feels like a lead single, right up through to the 11-minute closer, "Desolation Row." Highway 61 is chaotic at times, but always laser-focused and a must-listen for anyone exploring Dylan's back catalog.

Fun Fact: Highway 61 is a real road that runs from Dylan's home of Duluth, Minnesota, all the way south to New Orleans, Louisiana.


3rd Choice: The Freewheelin' Bob Dylan

Before he became known for his surreal lyrics and rock-folk sound, Dylan made a name for himself as a protest folk singer, often relying on nothing more than his guitar and harmonica. It was the LP, The Freewheelin' Bob Dylan, that made Dylan a star. Indeed the album earned Dylan the moniker, "Spokesman for a Generation." Though he viewed that title with some degree of disgust, there's no denying he became a cult figure.

Opening with "Blowin' In The Wind," a song that might be the anthem of the 1960s, the album is perhaps best known for articulating the generational anxieties that many felt during that time. But, while there's plenty of political and social commentary throughout the album, it reaches its true highs with songs of love and heartbreak, such as "Girl From The North Country" and "Don't Think Twice, It's All Right."

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Fun Fact: Though not his first album, The Freewheelin' Bob Dylan would be the first to really showcase Dylan's songwriting skills, as his previous self-titled effort only features two original songs.


Fan Favourite: Blood On The Tracks

Dylan has had more comeback albums than most artists have albums, but one of his earliest comebacks, Blood On The Tracks, would also prove one of his best. It's also one of the few albums he wrote that not only stands up to his 60s heyday but arguably outperforms it.

Though Dylan denies that the album is autobiographical, most critics link Blood On The Tracks lyrical themes and urgency to tension occurring in his personal life. Whatever the case, it certainly seems that Dylan had a fire under him when penning these tunes.

Fun Fact: Recording sessions for Blood On The Tracks produced one of Dylan's greatest hidden gems: "Up To Me." That this song never made the album is a testament to how good it is. (Dylan opted for the short "Buckets Of Rain" instead). Once you're done listening to Blood , do yourself a favor and seek out "Up To Me," as it serves as something of an epilogue to the experience.


Avoid: Self Portrait

As mentioned, Dylan had a lot of comeback albums, which insinuates that he also had some LPs that didn't go down well with fans. The truth is, despite his undeniable songwriting talent, he has had a fair share of misfires. Indeed, from his misguided ventures into synth territory to half-hearted cover albums, to a trilogy of born-again Christian LPs, it feels as if there were times when Dylan was attempting career suicide.

Self Portrait is not the worst LP Dylan made, but it's the one you're most likely to bump into, coming right at the tail end of his heyday. Dylan himself viewed the album as a joke designed to end the cult of personality forming around him. That said, it's not entirely without merit, and there's a handful of hidden gems to explore here. Just wait until you've become acquainted with the rest of Dylan's back catalog first.

Fun Fact: When asked why he made Self Portrait a double album, Dylan replied, "if you're gonna put a lot of crap on it, you might as well load it up!"


Underrated: New Morning, 1970

Dylan has such a vast discography and is such a talent that he has forgotten albums so good that they would be a crowning achievement for anyone else. However, his 1970 album, New Morning, might be the most underrated of them all.

The problem with New Morning is that it came only mere months after the aforementioned Self-Portrait. So, while some heralded it as a return to form, Dylan had, perhaps intentionally, lost a portion of his audience by that time. Stylistically, it's relatively similar to that album, featuring the country sound Dylan had been experimenting with since Nashville Skyline. The difference is a better production and a whole load more passion.

Fun Fact: While recording New Morning, Dylan received an honorary doctorate from Princeton University. Sounds great, but Dylan felt the experience was negative and wrote the cynical "Day Of The Locusts" in response.

This content is accurate and true to the best of the author’s knowledge and is not meant to substitute for formal and individualized advice from a qualified professional.

© 2022 Mike Grindle

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