The Beginner's Guide To Bob Dylan

If I could go back and discover Bob Dylan, this is the path I would take, so good luck, if you're not already a fan:

Bringing It All Back Home (*****)-1965
Dylan’s Second Coming Album. Better place to start than any. First half jamming, second half folking; kicking off with “Subterranean Homesick Blues” and closing with “It’s All Over Now, Baby Blue”, it’s his most structured album of the 60’s. Sensational lyrics and very accessible, it also includes the well-recognizable “Mr. Tambourine Man” and two gorgeous love ballads that put Paul Simon to shame, “She Belongs To Me” and “Love Minus Zero/No Limit”. The first of his epic trilogy, my only complaint is that is should have included “Positively 4th Street”.
Favorite Track- Love Minus Zero/No Limit

Highway 61 Revisited (*****)-1965
Dylan’s Head Album. My favorite Dylan album and his most heartfelt. Simply a rock album never to be matched in terms of artistic intensity and brutal emotional power. It’s like watching a cold-blooded murder and a childbirth at the same time. Get this one before 'Blonde On Blonde' for sure.
Favorite Track- Queen Jane Approximately

Desire (*****)-1976
Dylan’s Gypsy Album. Again, very accessible. A huge departure from ‘Highway 61’, but it’s a wonderful introduction to the wild spirit of this artist and his scope. And Emmylou Harris sounds beautiful. Beginners are naturally attracted to the epic “Hurricane”, but once you get past that hump, it’s a treasure chest waiting to be found. Many bright textures and stops along the way (Mozambique to Mexico to wild unknown country) and on par with the best storytelling I’ve ever heard, it can virtually never get old. The first side is maybe the best album side of the 70’s and the ending is endearing and classic Dylan.
Favorite Track- Isis

Blood On The Tracks (*****)-1975
Dylan’s Heart Album. As lovely and bright as it is lonely and sad, this is about the most essential American album I can think of. A must-hear after ‘Desire’ because it’s harder to swallow, but it’s more fluid and intimately passionate.
Favorite Track- Tangled Up In Blue

Blonde On Blonde (*****)-1966
Dylan’s Altered State Album. Mostly regarded as the peak of Dylan’s songwriting and charisma, this one’s a doozy. Perhaps the first double LP,well, ever, it’s a long rollercoaster that takes some warming up for. I would say it’s his most creative and mysterious conception and that it is likely to be the most addicting album of his upon introduction. The lyrics alone are ridiculously stimulating.
Favorite track- Absolutely Sweet Marie

Live 1966- Royal Albert Hall Concert (*****)-1998
Dylan’s “You’re A Liar!” Album. A mildly-vivacious revisit of the folk material, and ultra-vivacious introduction to Dylan and The Band’s unadulterated spitfire live show. Complete with sneering comments like “Judas” and Dylan’s f*ck this attitude towards the listener’s such as “I don’t believe you, you’re a liar!” In the end, noone wins, but everyone was a little less ordinary. A good companion to “Blonde On Blonde”.
Favorite Track- I Don’t Believe You (She Acts Like We Never Have Met)

The Freewheelin’ Bob Dylan (****)-1964
Dylan’s Ragtag Album. The finest of Bob’s folk albums and the pinnacle of the protest-oriented middle 60’s. The album is pretty touching, but it’s less essential to a collection mostly because his later albums are so strong (the next year he had not one-but two absolute classics).
Favorite Track- Don’t Think Twice, It’s Alright

Live 1964 (***1/2)-2004
Dylan’s Halloween Album. A perfect companion to the folk albums. At only age 23, it was clear he would leave a big imprint in rock.
Favorite Track- One Too Many Mornings

Another Side of Bob Dylan (****)-1964
Dylan’s Other Folk Album. It seems to be underappreciated or underrated, or whatever, but it again displays Dylan in a great artistic period, and it musically begins to set him apart from the pack, more than ‘Freewheelin’.
Favorite Track- It Ain’t Me, Babe

Nashville Skyline (*****)-1967
Dylan’s “That’s Right, I Can Play Country” Album. From the first tune, “Girl From the North Country”, a duet with the late Johnny Cash, it was apparent that Dylan had gotten all of the sarcasm out of his system. This music is simple and straight forward. It’s super sweet and contains the timeless, “Lay Lady Lay”, further proving Dylan’s consistency at altering the popular view of him.
Favorite Track- Lay Lady Lay

John Wesley Harding (****1/2)-1969
Dylan’s “That’s Right, I Can Sound Dated” Album. The most enigmatic Dylan album and infinitely enjoyable to boot. Definitely no starting point for any listener, but along with The Band’s self-titled album of the same year, a brilliant close of the 60’s for an artist that changed the face of culture.
Favorite Track- I Dreamed I Saw St. Augustine

Other Albums Much Worthy of Mention:
Live 1975
The Basement Tapes
Time Out Of Mind
Love and Theft
New Morning