What are the most valuable Bob Dylan albums?

A young Bob Dylan with Joan Baez

Bob Dylan is, put simply, a legendary singer-songwriter. In 2016, he became the first songwriter ever to win the Nobel prize for Literature.  He has left his mark on the world of music and popular culture with the depth and meaning of his lyrics, and distinctive voice.

Over the course of a career spanning six decades and beyond, Dylan’s body of work stands scrutiny with the best. Lesser mortals would be pleased with having written and performed just one of his albums. He has at least five that can justifiably be considered classics; jewels of modern pop culture which have been enjoyed by countless millions since the early sixties.

Above and beyond their musical and lyrical excellence, some of Dylan’s albums are worth substantial amounts as physical artefacts. Here, I will explore the most valuable Bob Dylan albums, peering into their backstories. What makes them significant? What is their cultural impact, and, of course, how much could they be worth?

The Albums

The Freewheelin’ Bob Dylan (1963)

Dylan’s second studio album, The Freewheelin’ Bob Dylan
is a significant marker in his musical and lyrical development. It showcases his poetry and his folk sensibilities. Classics like Blowin’ in the Wind and Don’t Think Twice, It’s All Right make it the ideal primer for those new to Dylan.

Due to its historical importance and critical acclaim, original pressings of this album, especially the ones featuring four rare songs subsequently removed from the album, hold significant value in the collector’s market.

In July 2022, an original and extremely rare stereo copy of The Freewheelin’ Bob Dylan sold for a total value of $150 000 at Heritage Auctions, of Dallas, TX.

This version of Dylan’s iconic LP had four tracks removed after the initial pressing, to be replaced by others on subsequent releases. These tracks —Rocks and Gravel, Let Me Die in My Footsteps, Gamblin’ Willie’s Dead Man’s Hand and Talkin’ John Birch Blues are all found on the red Columbia labels, and on the record itself.

However, the sleeve lists the four replacement tracks, namely Masters of War, A Hard Rain’s A-Gonna Fall, Bob Dylan’s Dream and Talkin’ World War III Blues.

Dylan had been prevented from performing Talkin’ John Birch Blues on an edition of the Ed Sullivan show so he made the decision to cull that track. However, why the other three were removed remains shrouded in intrigue.

Protest songs

The Times They Are a-Changin’ (1964)

An evocative, nay provocative title, The Times They Are a-Changin’, suggests change is afoot both for Dylan and perhaps American society. For a start, there are no cover versions. Dylan’s own compositions populate it in its entirety.

Encapsulating the social and political turmoil of the 1960s, from civil rights to Vietnam, this album demonstrated another stage in Dylan’s evolution as a songwriter. It also highlights his strong conviction regarding the issues that were affecting, not only young people but society in general.

There’s a battle outside ragin’

It’ll soon shake your windows

And rattle your walls

For the times they are a-changin’

In addition to the title track, other tracks such as With God on Our Side and Only a Pawn in Their Game stand out particularly.

Original mono pressings of this album are highly sought after, especially those with the original track listing. In addition, a white label demo pressing, released to radio stations in December 1963 is particularly desirable. Heritage Auctions sold a copy in November 2022 for a thousand dollars.

Going electric

Bringing It All Back Home (1965)

His fifth album, Bringing It All Back Home was a seismic moment in Dylan’s career. For the first time, he used electric instruments in his music. Many in the folk movement, including Irwin Silber and Ewan MacColl were extremely critical. They argued that Dylan was moving away from political songwriting, with Silber being especially outspoken.

This album features side one, an electrically backed first side, with an all-acoustic side two. Instead of regressing, as his critics suggested, Dylan was showing his versatility and expanding not only his own but other people’s musical boundaries.

Stand-out tracks include Subterranean Homesick Blues, Mr. Tambourine Man, and It’s Alright, Ma (I’m Only Bleeding). Whilst it is true that this album does not include exclusively political or socially aware lyrics songs, Maggie’s Farm is an outstanding example of political and social commentary.

Reissues, especially signed ones, can sell for a pretty penny. In 2021, Heritage Auctions sold a signed reissue for $4 500. In 2022, the same auction house sold a white-label copy for $2 625.

Highway 61 Revisited (1965)

Many see this album as Dylan’s best. He uses blues musical techniques to augment the delicate, yet occasionally damning poetry of his lyrics. Here is Dylan, no longer just a folk musician, but now an icon of rock n’ roll.

Following a tour to the UK, Dylan had returned home dissatisfied with his material. Upon his arrival, he had sat down and ‘vomited’ twenty pages of verse.

Cleansed and reinvigorated by this activity, Dylan reduced those twenty pages to four verses and a chorus. Like a Rolling Stone was born. Its use of different musical techniques, Dylan’s energetic delivery, coupled with the bold candour of the lyrics meant it was revolutionary.

The album contains other standouts, such as Ballad of a Thin Man and Desolation Row and was almost entirely recorded with electrical backing. In fact, only the eleven-minute-long Desolation Row
is acoustic.

In August 2022, Goldin Auctions of Runnemede, NJ sold an original mono pressing for $4 400 which rose to $5 280 including Buyer’s Premium.

Dylan as genius

Blonde on Blonde (1966)

Continuing seamlessly from Highway 61, Blonde on Blonde is another epic album. Dylan was perhaps at the peak of his powers as recording began just four months after the sessions for Highway 61.

One of the first double albums, Blonde on Blonde is seen by many as one of the greatest popular music albums. It shows Dylan’s lyrical genius and experimental approach to music, with aspects of rock, folk, and blues.

Rainy Day Women #12 & 35, Visions of Johanna, Sad Eyed Lady of the Lowlands are tracks of such range and subtlety, from the twelve-bar blues of Rainy Day Women to the eleven minute opus that is Sad Eyed Lady of the Lowlands.

An original mono pressing sold on eBay in 2020 for $2 260s. Whilst in January 2023, Heritage Auctions sold a signed reissue for $4 750 including Buyer’s Premium. In April that year, Sotheby’s sold a signed album cover for $6 096.

Artistic and cultural value

Bob Dylan artistic influence

As befits a Nobel laureate, Dylan’s discography contains a range of incredible albums that chime with listeners and have influenced innumerable artists.

It is true that all his albums are of artistic and cultural value. Some of them, as individual, physical artefacts also have significant monetary worth among collectors. From the socially conscious anthemic The Times They Are a-Changin’ to the electrical innovation of Bringing It All Back Home, each album represents a milestone in Dylan’s career. Sometimes they are an ever-so-subtle adjustment or in the case of Bringing It All Back Home, a tectonic shift.

Either way, along with The Beatles, Elvis or the Sex Pistols, Dylan’s albums are signposts in the evolution of popular music. Whether for their historical importance, rarity, or just Dylan’s genius, these valuable albums are a testament to his legacy and impact on the music industry and popular culture.

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