With the release of A Complete Unknown, the man, the myth, the legend that is Bob Dylan was introduced to a new audience. And with that new audience comes a lot of people asking where to start with this behemoth of a discography. So I figured, as a certified Dylan nerd myself, I would just write out this helpful guide of what I would recommend people new to Bob seek out.
1. No Direction Home (2005)

Now that you’ve seen A Complete Unknown, I recommend watching No Direction Home. It’s an amazing two-part documentary by Martin Scorsese that covers the same period of his career that A Complete Unknown covers. It features great footage, informative testimonials, and is quite possibly the most honest interview Bob Dylan has ever given. Seeing this on VH-1 Classic in junior high started my own Dylan obsession, so I can’t recommend it enough.
2. The Original Mono Recordings (2010)
This entry is kind of cheating since it’s literally just a box set of his first eight albums (1962’s Bob Dylan – 1967’s John Wesley Harding), but damn it, all eight of these are essential Bob. Also, them all being presented in their mono mixes is a treat. This is how most people would have heard them back in the day. Albums in this set I would recommend you start with are Highway 61 Revisited and The Freewheelin’ Bob Dylan. If you listen through these albums and don’t find anything you like, you’re wrong. Listen again.

3. Blood on the Tracks (1975)

This is probably Bob’s most accessible album. Even if you don’t like Bob Dylan, or the usual Dylan tropes, I feel like you can still find this album enjoyable. It’s also him at his most relatable. It’s a divorce album, so it’s drenched in heartbreak. If you listen to this album and don’t feel anything, go see a doctor.
4. The Bootleg Series Vol. 5: Bob Dylan Live 1975, The Rolling Thunder Revue (2002)
Yes, a live album. But not just any live album. One of the greatest live albums. These performances are quite possibly Bob’s greatest. With this, you get a lot of radically reworked 60s songs, which really just shows how much of a shapeshifter he is. And you get a lot of performances of songs from his then upcoming 1976 album Desire that are, in my opinion, better than the studio versions.

5. “Love and Theft” (2001)

Yes, we’re making quite the time jump here. Not to say there aren’t albums in the 80s worth checking out (Shot of Love, Infidels, and Oh Mercy), nor am I downplaying the importance or greatness of 1997’s Time Out of Mind, but this was the first album outside of his 60s and 70s output that I fell in love with. I think this is a great gateway to Bob’s latter day work.
Of course this is just a starting point. A launching pad. Hopefully these grab you the way they grabbed me, and countless other Dylan heads. I’m jealous of new fans that get to experience Bob Dylan’s discography for the first time.