Welcome back to Music Monday. This week’s Music Monday is going to be all about Bob Dylan’s first 5 albums. Bob Dylan is one of the most influential artists of all time, let alone in folk music. Bob Dylan is widely known as one of the greatest lyricists ever and often sings about social issues, politics, love, and religion.

Bob Dylan is one of my favorite musicians and is one of my biggest inspirations and influences when I write my own music. I’ve only been listening to Bob Dylan for a short period of time, but he continues to be a constant listen when I need some inspiration, when I need to focus on some homework, or when I just need to relax.

Here are my top songs from each of his first 5 albums:

In My Time of Dyin’, Bob Dylan

Bob Dylan’s debut studio album, The 3rd track “In My Time of Dying” was originally recorded by gospel blues artist Blind Willie Johnson in 1927 under the title “Jesus Make Up My Dying Bed”. While famously covered by Led Zeppelin on their 1975 album Physical Graffiti and by Bob Dylan on his 1962 debut album, the song is a traditional gospel spiritual with unknown origins. Bob Dylan often sings about the loss of others and mourning through death and love, his raw emotion arrangement of Jesus Make Up My Dying Bed shows how influenced by traditional blues shaped his music.

This song is what I used to learn how to play slide guitar and has helped me learn how to sing and play at the same time. Bob Dylan’s music has always challenged me with complex lyric changes and rhythmic guitar parts that continue to push me to learn how to play the guitar better and better.

HM: House of the Risin’ Sun

Don’t Think Twice its Alright, The Freewheelin’ Bob Dylan

Featured on The Freewheelin’ Bob Dylan, “Don’t Think Twice, It’s All Right” is one of Bob Dylan’s most well-known early songs, released in 1963 during the height of the American folk revival. The album itself marked a major step forward from his debut, consisting almost entirely of original material and establishing Dylan as a serious songwriter rather than just a performer of traditional songs. The song draws melodic inspiration from “Who’s Gonna Buy You Ribbons When I’m Gone,” recorded by Paul Clayton, showing Dylan’s tendency to reshape existing folk ideas into something personal.

It was written around the time that Suze Rotolo, Dylan’s girlfriend at the time, indefinitely prolonged her stay in Italy. The beginning of the melody is based on the public domain traditional song “Who’s Gonna Buy Your Chickens When I’m Gone”, which was taught to Dylan by folksinger Paul Clayton, who had used it in his song “Who’s Gonna Buy You Ribbons When I’m Gone?”

Bob Dylan’s love songs and lyricism sit so well with me. Because no matter who you are and who you’ve loved, every phrase can speak to a part of your life. On top of being a lyrical genius, his fingerpicking style continues to push the limits of my guitar playing, and listening to this song in the car with my older brother for the first time, we kept repeating this song over and over, picking apart what each chorus means.

HM: Blowin’ In the Wind

The Times Are A-Changing’, The Times Are A-Changing’

The title track of The Times They Are a-Changin’, released in 1964, became one of Bob Dylan’s most iconic protest songs. The album itself is considered his most politically focused work, written during a period of major social and political upheaval in the United States, particularly surrounding the civil rights movement. Dylan intentionally stripped back the sound, focusing on stark arrangements to emphasize the weight of the lyrics.

Dylan recalled writing the song as a deliberate attempt to create an anthem of change for the moment. In 1985, he told Cameron Crowe. “This was definitely a song with a purpose…”

Whenever I listen to this song, no matter how corny it reminds me that my time and life are going to change very soon, going to college and not seeing many of my friends as often as I do now. I know that my life is gonna change for the better.

HM: When the Ship Comes In

It Ain’t Me Babe, Another Side of Bob Dylan

Appearing on Another Side of Bob Dylan, “It Ain’t Me Babe” marks a noticeable shift in Dylan’s songwriting from outward political commentary toward more personal and introspective themes. Released later in 1964, the album surprised many listeners who expected more protest songs, instead presenting a more abstract and emotionally complex direction.

The song rejects the idea of being someone’s savior, opposing the traditional love songwriting of Dylan. His lyrics are direct and repetitive, reinforcing his emotional independence. This reflects a broader transition in his life and career, as he began distancing himself from both political expectations and personal attachments. The album captures a turning point where Dylan starts to redefine himself as an artist, moving away from labels and toward a more individual voice.

My most recent memory with this song is when I was hiking with 3 of my best friends through Auxier Ridge in Red River Gorge. After listening to the corniest 2000’s pop anthems, we decided to switch it up and listen to this right as we reached the lookout point. Being my senior year and knowing I won’t get to hang out with this group of friends, it was a bittersweet moment, yet one of my favorite memories.

HM: My Back Pages

Maggie’s Farm, Bringing It All Back Home

From Bringing It All Back Home, “Maggie’s Farm” represents a major turning point in Bob Dylan’s career as he began shifting toward electric instrumentation and a more confrontational sound. Released in 1965, the album is split between electric and acoustic sides, symbolizing his transition away from traditional folk into a more modern, amplified style.

The song uses the metaphor of a farm to critique authority, labor, and societal expectations, with each verse introducing a different character representing control or exploitation. Dylan ultimately rejects them, declaring he will no longer “work on Maggie’s farm,” a line often interpreted as his refusal to conform to expectations from the folk community and the music industry. This period famously led to controversy, especially his electric performance at the Newport Folk Festival, where audiences were divided over his new direction. The album and this song in particular capture Dylan asserting full creative independence, reshaping both his image and the future of popular music.

I showed this song to my little sister to introduce her to Bob Dylan, and she was so intrigued by his lyrics and singing style. Fast forward a few days, I walked into the garage after getting home, and there she was listening to Bob Dylan while playing outside. Bob Dylan hasn’t only helped me find my musical voice but has connected me deeper with some of the best friends I have, and connected my sister and me even more.

HM: Mr. Tambourine Man and Subterranean Homesick Blues