Few artists in history have captured the human experience—its pain, hope, and heartbreak—quite like Bob Dylan. With a career spanning more than six decades, Dylan’s words have inspired revolutions, comforted the broken, and moved millions to tears.
Here are 10 Bob Dylan songs that will touch your heart and maybe, just maybe, make you cry.
1. “If You See Her, Say Hello”
From Blood on the Tracks, this song is one of Dylan’s most heartbreakingly honest moments. It captures the quiet pain of seeing someone you loved move on while you’re still standing in the same emotional place.
His voice trembles between regret and acceptance, and every line feels like a letter you never sent. “If you see her, say hello, she might be in Tangier…” — it’s not just a lyric, it’s a wound still open.
2. “Girl from the North Country” (1963)
One of Dylan’s most tender love songs. His longing for a past lover and the wistful tone make this song deeply emotional. If you’ve ever missed someone, this one will hurt.
3. “Most of the Time” (1989)
From Oh Mercy, this song is a masterclass in emotional denial. Dylan sings about moving on — he insists he’s fine, that he doesn’t think about her anymore — yet every line betrays the truth: he still misses her deeply.
The calm rhythm hides a deep ache beneath the surface. It’s the sound of someone trying to convince themselves they’ve healed, while still bleeding inside.
“Most of the time, she ain’t even in my mind…” — but you know she always is.
4. “Boots of Spanish Leather” (1964)
A dialogue between two lovers parted by distance. The bittersweet ending reminds us that love sometimes fades without blame—just silence.
5. “It’s All Over Now, Baby Blue” (1965)
This poetic masterpiece captures the moment when something ends—love, friendship, or innocence. It’s beautiful and devastating all at once.
6. “You’re a Big Girl Now” (1975)
From Blood on the Tracks, this song captures the raw pain of letting go. Dylan’s voice quivers with heartbreak as he watches someone he once loved grow beyond him.
It’s not angry — it’s sorrowful, tender, and full of acceptance. The song feels like the quiet moment after love dies, when you realize you can’t go back.
“Love is so simple, to quote a phrase…” — yet nothing about this moment feels simple.
7. “Sara” (1976)
Written about his then-wife, this song is raw, personal, and heartbreaking. Dylan rarely opened his soul like this—“Sara” feels like a love letter written too late.
8. “Not Dark Yet” (1997)
A reflection on aging, mortality, and fading light. It’s one of Dylan’s most haunting works—proof that his poetry only grew deeper with time.
9. “Every Grain of Sand” (1981)
Spiritual and deeply human, this song speaks to anyone searching for meaning. It’s Dylan at his most vulnerable, acknowledging both sin and grace.
10. “Ballad of Hollis Brown”
A bleak, chilling narrative about a poor South Dakota farmer driven by desperation to kill his family and then himself. It’s a gut-wrenching portrait of economic hardship and ultimate despair.
Written by Turkish Dylanista
