After dedicating 1 hour to the listening of all these songs, you won’t find another opportunity to spend a better 60 minutes. These sounds and words never fail to musically paint the time they were created in while providing lessons and insight along the way.

1. “Don’t Think Twice it’s Alright” The Freewheelin’ Bob Dylan, 1963.

With 23 years of my own, it is simply amazing that a 22 year old Bob Dylan began writing some of the greatest folk lyrics of the time and was on a journey that eventually led him to be one of the highest ranking folk musicians of all time. This song is a premier example of how Dylan was able to use only his words, fingers, and mouth-harp with a complexity and relatability that connects with so many people. If I play a Dylan song at open mic, 8 times out of 10 it’s this one. The picking style is fun to mess around with and the lyrics are so good I never forget them on stage. Nothing beats playing this song in a silent bar with a pretty girl staring at you while her boyfriend is efficiently digesting that one special ingredient in beer which allows him to unblinkingly glare at you throughout the duration of the song. The perfect balance of comfort and fear.

2. “North Country Blues” The Times They Are a Changin’, 1964.

You can see Bob play this at the 1963 Newport Folk Festival on YouTube here: https://www.youtube.com/watch?v=8ol_W8hyHaE

It’s eerie watching such a young man channel the hard times of a family living in a fading iron ore town. His lyrics deliver imagery so vivid you can find yourself transported to the past, living and seeing through another’s eyes the decline of a once prosperous town. And he can’t even find his own pick right at the beginning.

3. “Boots of Spanish Leather” The Times They Are a Changin’, 1964.

This back and forth between separated lovers exploits short poetic letters to show the effects of changing desire and disillusioned love. I’ve played and sang this song many times before at open mic and it takes a miracle to have the crowd pay attention for too long because there’s about one million verses. But because every verse is so well written I still play it anyways and sort of just stand there singing to myself for a while.

4. “I Want You” Blonde on Blonde, 1966.

In my opinion this is one of Dylan’s happiest songs. The sound is incredibly mood enhancing with the guitar and flute simultaneously dotting the chorus in smooth melodic phrases. I admit a partial bias to this song because it was playing during a very special time for me when I was in high school. Decode that however you want but i'll tell you that it wasn't on school grounds.

5. “The Ballad of Frankie Lee and Judas Priest” John Wesley Harding, 1967.

I’ve always been able to imagine this vivid story in my head whenever I listen to this song. The slow marching rhythm propels the narrative while I see these characters interact with each other. To me the song is about trust and shows how someone with control can lead others either astray or in the right direction by suggestion and the creation of expectations. Sometimes your Frankie Lee, sometimes your Judas Priest—that’s Judas Priest as in Dylan’s fictional character, not the band I used to listen to whenever I ran on a treadmill.

6. “Lay, Lady, Lay” Nashville Skyline, 1969.

Dylan’s low velvety voice in this song is such a turn from his usual nasally cigarette scratch and I’m a huge fan of both. It fits perfectly with the romantic wailing of the pedal steel guitar in the background. Not to mention he expertly sings “Why wait any longer for the world to begin? You can have your cake and eat it too”—words to live by.

7. “It Hurts Me Too” Self Portrait, 1970.

Covered by Dylan, The Rolling Stones, as well as The Grateful Dead, this classic blues tune has been passed around a lot and I’m absolutely thrilled it made it to Dylan’s hands.

8. “Meet Me in the Morning” Blood on the Tracks, 1975.

Entrancing. Brimming with groove.

9. “Love Henry” World Gone Wrong, 1993.

With the liquid strumming and aged voice in this song, again I am driven through another plot of masterful writing. A jealous lover murders poor Henry so the woman he loves will feel the pain of him not returning. After dropping him in the well she tells the parrot who saw the murder not to reveal it but it doesn’t trust her. It is a safe assumption that she'll kill the bird because she offers him gold just as she had offered it to Henry before his death. She probably should have offered the parrot a cracker before immediately going to gold. It reminds me of a Tom Waits quote; “Some men will do it for diamonds, and some men will do it for gold”.

10. “Standing in the Doorway” Time Out of Mind, 1997.

Time Out of Mind is without a doubt one of my top Dylan albums. This particular track is something you may find yourself listening to at 2:30 am after a day filled with wrong turns, when you’re in your head too much. This song will calm you down giving you someone else’s brain to pick; the man with “blues wrapped around his head”.

A mere handful of the countless Dylan songs that solidify his reputation, this list serves as a rough description of what can be interpreted from one of the most influential and creative minds of all musicians and poets. The best part about his music is that others can go one hundred different ways with it and they’ll be just as right on as anyone else. Above all, it has taught me that to truly understand your own perception, you have to be able to spend time within another’s.