Bob Dylan’s best 25 songs.

Bob Dylan without a doubt is one of the most influential artist of this generation. He changed the ways songs could be written and the lyrics that could be used for a song. He has a career that has lasted decades and even with the normal ups and downs, Dylan remains an important figure in music. I want to share my favorites, there are many to choose but here it goes. 

  • The Lonesome Death of Hattie Carrol. Released on the album the times they are a changing in 1963. By this time a lot of Dylan’s songs had social events inspire the lyrics. I start with this one because I find the writing to be so clever and a right of point criticism of the justice system. The story is about a maid of a hotel killed by a rich white man. The song goes slowly telling the story and we learn the details Dylan sings in the chorus to those who philosophize disgrace to take away the tears because it was not the time to cry, but when the song reveals the sentence he got for the murder Dylan quickly changes and sings that now is the time for the tears. I find it so brilliant and a clever way to say just how racist was the system or some may argue still is. 

24. Like a Rolling Stone. Released on 1965 on the album Highway 69 Revisited, it is one Dylan’s most known song a true game changer, a song with no bridge or guitar solos and over 5 minutes of lyrics that just takes you on a wild ride. I really love the performance of the song; Dylan’s vocal is potent and sung with intent. 

23. Working man blues. This is from the album Modern Times released in 2006. I just find the lyrics explain what a working man goes through. 

22. Jokerman. Released on the Infidels album. I just love the melody and the lyrics are among Dylan’s best. 

21. License to Kill. Taken from the same album as Jokerman, this is such a great song on how mankind can destroy so much just because they have the power to do what they want. 

22. Desolation Row. Released on the Highway 69 Revisited, this is such a compelling song. People I know admire rappers for their lyric and rhyming of words, but I dare them to take a listen to Dylan. Take this song lasting over 10:00 minutes of pure lyrics only repeating the line Desolation Row. The way Dylan uses known character from fairy tales to Cain and able to describe a place where sadness apparently rules. This is not the only example of this kind of song but it is one of his best. 

21. One too many mornings. Released on the album The times they are a changing. This is a gentle love song of regret and maybe of a love ending. The sweetness of the melodies and the sorrows of the lyrics just show the sensitive poet in Bob Dylan. I just love the last verse, 

“is a restless hungry feeling that don’t mean no one no good

When everything I’m a saying you can say it just as good

You’re right from your side and I’m right from mine

We’re both just one too many mornings and 1,000 miles behind” Bob Dylan

20. Standing in the doorway. Released on the Time out of Mind album, this is pure poetry about a lover that has been left behind and does not if forgive her or not. I just love how the lyrics take us on how it feels to love someone still after it has ended. The melody is perfect for the feel of the song. 

19. Tempest. This is a crazy song but how good it is. From his last album of original songs, Tempest is a song about the sinking of the Titanic. It is a mix of fantasy and some true aspects of the events and even Leo gets mentioned. The song is over 12 minutes and never loses my interest in the song. Showing that by his 35thstudio album, Dylan could still provide songs that are inventive and full of stories. 

18. Changing of the guards. From the Street Legal album, this is one song I really can’t tell what is it about but I just love the lyrics and the melody so much that makes it one of my favorites. 

17. Don’t fall apart on me tonight. From the Infidels album, this is one that I love because of the lyrics. I just love how Dylan uses imagery to express a feeling, I have always loved and related to this verse:

“But it’s like I’m stuck inside a painting that is hanging on the Louvre 

My throat starts to tickle and nose itches but I know I can’t move” Bob Dylan

That is a line full of desperation and he sings it with such honesty in his voice. And it has a lot more great lyrics on this one like when he says he wished he could have been a doctor to save lives instead of burning every bridge he crossed. 

16. Not Dark yet. From the album Time out of mind, comes this song from the point of view of a man who is near the end. The lyrics are so beautiful and the melody so melancholic, just a perfect combination. 

15. Waiting for you. From the movie the Devine Secrets of the Ya-Ya Sisterhood comes this lovely song. I just love the lyrics and as a fan of the film, the songs fit perfectly to a few of the relationships in the film. I don’t know how known is it, but it is one of my favorites of Dylan. 

14. My Back Pages. Taken from Another side of Bob Dylan album, comes this great song maybe describing how Dylan felt about himself. 

13. Sad-eyed lady of the lowlands. How would he close the iconic Blonde on Blonde album? With an epic 14-minute epic of a song. The song is beautiful, poetic and classic Dylan. 

12. Every grain of Sand. He had a period where his albums were faith-based music and they were great. Of the period this one and I believe in You are my favorites. I chose this one because it is a song on just trusting God, trusting that he has control of every grain of sand just the last bit of hair on our heads. 

11. Make you feel my love. This is one of the songs that drew me more to Dylan when I heard a version recorded by Billy Joel. I just love the lyrics so much and at that time the words just felt like I could have written for the girl whom I had feeling s for at the time. It is a beautiful love song. 

10. Don’t think twice it’s alright. From the album Freewheelig comes this country song that I simply love, again Dylan just has a way with laying down beautiful lyrics. 

09. A hard rain’s a-gonna fall. From the freewheeling album also is a song full of prophetic lyrics. Things we now see like guns in the hands of our children, written in 1962 or 1963 is a song so poignant as Dylan asks his kid what things did he see. 

08. You’re a big girl now. From the Blood on the Tracks album comes one of Dylan most heartbreaking love songs. He is describing how that love ended and how she is a big girl now and might not need him anymore. The part where Dylan says he knows where he can find her and how that makes a big girl all the way, brilliant lyrics on this song. 

07. Restless Farewell. The released version is from the Times they are a changing but the version I love is a live version I found on YouTube, performed live by Dylan on Frank Sinatra’s 80thbirthday celebration. The lyrics are so moving and maybe a song that could precede the song My way as he goes explaining his life.

06. The times they are a changing. With lyrics that seemed like a warning of the times ahead and when you look at he was right on point. 

05. Chimes of freedom. This song is simply beautiful both in melody and the lyrics. A song for the unlucky and the forgotten, as Dylan sings that for every hung-up person in the whole universe, the chimes of freedom are flashing. The Byrds did a beautiful cover version of this song though they left out a lot of the verses. 

04. Mr. Tambourine Man. A classic song by Dylan. I think anyone who at one time was not able to sleep this song is a plea for something to take your mind away to a better place and the writer is saying basically I will cooperate, just take me away. 

03. Tangled up in blue. This is a raw acoustic song that just hooks you right from the start. I really just love the lyrics on this one and Dylan performance. 

02. Cross the Green Mountain. Another film song, this one left me amazed at how Dylan captured the spirit of the Civil War. The lyrics and the music are both filled with a melancholy feeling that has to be present at times of war.

01. Mississipi. From the album Love and Theft this has been my favorite Dylan song right from the first time I heard it. I just love the lyric and how sometimes we all can feel like all we did wrong was stay in a place for too long. 

01. (tie) Series of dreams. This song went unreleased until the first Bootleg series was released. Why was it not included, I don’t know. The music is haunting and the lyrics are amazing. 

There are a lot of songs that I did not include and that just shows the amount of good songs Dylan has recorded. I could also mention

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