I remember so desperately wanting to get into Dylan, because not only is he a cultural icon and legend, who brought about many of the societal and music changes that we remain thankful for today, but his music was of such depth, intellectually and emotionally, that I knew I needed it in my life. However, I didn't really know where to start and had a hard time realizing how good his voice really was, and although each person's discovery should be their own, here are some door-openers into the world of Dylan.
1. "Tangled Up In Blue"
Though this song consists of only guitar, drum, and Dylan's voice, when the drum hits the downbeat and Dylan's voice takes off, it goes right to your soul and completely changes you as a person. It's off of his 1975 "Blood on the Tracks" album, recorded around the time of his divorce with his first wife, Sara.
Thus, the pain is visceral, and the raw emotion flooding from a man as reserved as Dylan drags us to the depths of emotional pain. Plus the lyrics are typically gorgeous, with a simplicity that makes the emotion even rawer.
2. "Visions of Johanna"
A lyrical masterpiece, and one that chills you and takes a hold of your every neuron in a way you didn't think possible. You're completely transported to a place where loneliness and confusion swirl in the air like mist after rain. If you want to know why music makes people do the things they do, listen to this song. The instrumental backing deserves much praise for this affect, as well as Dylan's voice, which arguably reached its storytelling peak around the time of this record, on 1966's Blonde on Blonde.
3. "It Ain't Me Babe"
This song has all the sadness and isolation that's at the root of many Dylan songs, but it's the reservation, the acknowledgment that the singer has already accepted that they'll never see the subject and is okay with that, that really makes us listen. It's got an almost apologetic tone as if the singer wishes they could stay but knows there'd be no love lost, and it's Dylan's atypical ruefulness and the clever use of guitar that makes this an easy-to-listen-to but hard-to-hear song.
4. "Like a Rolling Stone"
Bruce Springsteen once said that this song's opening beat "kicked open his mind", and he wasn't wrong. This number was named the best song ever recorded by Rolling Stone magazine, and it's diatribe against society and Dylan's searing "How does it feel?" grab you by the throat and never let go. It's also a good transition point from Dylan's folk to his rock, so you can enjoy the poeticism and social critique of the former with the good beat of the latter.
5. "Positively 4th Street"
This song is Dylan at his harshest, with the lyrics almost physically biting their subject. But the music itself is probably the best of Dylan's career, and has a nice, upbeat, Beatle-y feel to it, so the juxtaposition between the lyrics and the music as well as the quality of said music makes this a good song, and a nice way to enjoy Dylan without putting in so much effort.
1. "Don't Think Twice, It's All Right"
2. "Shelter from the Storm"
3. "Masters of War"
4. "It's All Over Now, Baby Blue"
5. "Percy's Song"