As yet another Valentine’s Day slips by, one age-old question lingers in the air: what truly qualifies as the greatest love song ever written? The debate has raged for decades, with no clear consensus in sight. Despite this, many have endeavored to claim the title for their own, showcasing their unique perspectives on what love in music truly means.
In a thought-provoking piece from the Harvard Gazette in February 2026, esteemed Harvard faculty members shared their insights on this timeless question. One standout choice came from Richard F. Thomas, the George Martin Lane Professor of the Classics and author of the acclaimed book “Why Bob Dylan Matters.” His pick for the ultimate love song? Bob Dylan’s haunting ballad, “Boots of Spanish Leather,” released in 1964.
Dylan, known primarily as a poet, crafted a piece that embodies the essence of doubt and longing in love. Thomas explained his choice, noting, “A real love song is one in which there’s doubt that the love is reciprocated, that we never really know the mind of another person.” He went on to praise Dylan’s ability to capture the complexities of human emotions in his lyrics, elevating his work to a level of profound artistry.
Recorded in the summer preceding its release, “Boots of Spanish Leather” is believed to be inspired by Dylan’s former girlfriend, Suze Rotolo. Rotolo, who dated Dylan during his early rise to fame in New York, passed away in February 2011, forever immortalized in the poignant lyrics of the song.
Thomas, renowned for his courses on Dylan’s impact on culture and literature, has shed light on the timeless nature of the musician’s work. Drawing parallels between Dylan and ancient poets like Catullus and Virgil, Thomas emphasized the enduring relevance of Dylan’s songwriting prowess.
In the world of music and love, there exists a vast landscape of interpretations and emotions. Each song, each lyric, carries with it a unique tale of love and loss, longing and hope. As we navigate the melodies of our own lives, let us find solace in the words of the poets and musicians who have paved the way for us to express the ineffable power of love.
Peace Nero is a writer and blogger who loves to explore different topics of self-development. She shares her personal experiences in order to help people discover their true purpose in life.