With an artist of Bob Dylan’s stature (and who has released as many albums as he has, 33 studio albums thus far) it can sometimes be difficult for new listeners to know where to start. Often times people start with greatest hits albums and I suppose that can be a decent way to dip your toes in but with Dylan I think you’re much better off experiencing his albums as a whole. Anyway, without further explanation, these are the five most essential Dylan albums.

1963 – The Freewheelin’ Bob Dylan

Dylan’s second album and his first to mostly feature his own songs (his debut album only included two Dylan originals.) It best captures his early acoustic folk period and includes some of his most famous songs like “Blowin in the Wind” and “A Hard Rain’s a-Gonna Fall.”

Incredibly, this album was recorded when Dylan was just 20 & 21 years old. That he was able to write such timeless classics as these at such a young age is amazing to me. Listening to “Masters of War” now, 46 years after it was recorded, it gives me goosebumps and it’s still just as relevant today as it was in 1963.

1965 – Bringing It All Back Home

This is the transition album from acoustic folk Dylan to electric rock Dylan. It opens up with the song that some folks like to call the “first rap song” (that’s “Subterranean Homesick Blues”) and also includes some of his other best known songs such as “Maggie’s Farm,” and “Mr. Tambourine Man.” This is the first of three consecutive Dylan albums included in this list of five.

1965 – Highway 61 Revisited

This may be my favorite Dylan album. And not so much just because it opens with “Like a Rolling Stone” (actually I’ve heard that song so many times that I sometimes skip it) but because it just keeps coming at you with amazing stories (that can be taken about a thousands ways each) and music that’s interesting to match. “Ballad of a Thin Man” is probably my favorite song on the album (and possibly my favorite Dylan song overall.)

1966 – Blonde on Blonde

Like with Highway 61 Revisited, Blonde on Blonde starts with a famous (and somewhat overplayed in comparison with the rest of Dylan’s catalog) song (in this case “Rain Day Women #12 & 35″) and just like with Highway 61 Revisited, it’s really the rest of the album that makes it among my favorites. Besides it’s many brilliant songs, this album is also notable for being the first double album in rock music (predating double album releases by Frank Zappa, The Beatles, and Jimi Hendrix.)

1975 – Blood On The Tracks

I really could have gone with a number of different albums (including 1997′s Time Out of Mind) for this 5th slot but in the end I had to go with Blood on the Tracks which opens with one of Dylan’s most well known songs “Tangled Up In Blue.”

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