There are few artists living today whose legacy can matchBob Dylan, but even with all the acclaim he’s received, so many of his records have been completely slept on. With 40 studio albums and almost as much bootleg material available, it can be difficult for listeners unfamiliar with his body of work to discern which records they should check out next. WhileTimothée Chalamet’s excellent performance in the Dylan biopicA Complete Unknownonly explored a brief period in his career, there’s far more to this singer-songwriter than just the mid-1960s.
Dylan’s greatest albumsare littered across his vast career as he’s continually reinvented himself across the decades and packed so many styles and genres into his work. From his poetic confessional songs as a young man to his grizzled wisdom in his later years,Dylan has played by his own rulebook, and his legacy is as somebody who never followed the crowd and always listened to his creative instincts. This uncompromising attitude meant that much ofDylan’s musichas been extremely underrated and should be reappraised by listeners as they look back on his extraordinary legacy.
5Another Side Of Bob Dylan (1964)
Bob Dylan’s fourth studio album
Another Side of Bob Dylanwas sandwiched between two undisputed classics,The Times They Are a-Changin’andBringing It All Back Home.
While the mid-1960s are the most revered era in Bob Dylan’s career, one great album often gets left out among the discussion of this highly prolific period for the famed singer-songwriter.Another Side of Bob Dylanwas sandwiched between two undisputed classics,The Times They Are a-Changin’andBringing It All Back Home, and felt more like a transition album as he inched ever closer to the controversial decision to go electric. Yet, this wasone of Dylan’s most confessional records, and to neglect it ignores important songs like “Chimes of Freedom” and “My Back Pages.”
4New Morning (1970)
Bob Dylan’s eleventh studio album
Following Bob Dylan’s reported 1966 motorcycle accident, the once-dubbed voice of his generation became increasingly reclusive as he rejected media attention, embraced family life, and settled down in Woodstock, New York. This more laid-back approach to living led to an acceptance of domestic bliss on songs like “Sign on the Window” onthe woefully underrated recordNew Morning. While this album is rarely spoken about in broad conversations around Dylan’s legacy, longtime listeners know that it truly was one of his best and a welcome return to nasally normality after the fascinating country voice he boasted onNashville Skyline.
3Shot Of Love (1981)
Bob Dylan’s twenty-first studio album
No era in Bob Dylan’s career is more divisive than his born again Christian phase, which resulted in the trilogy of records,Slow Train Coming,Saved, andShot of Love. This religious awakening meant that Dylan’s writing became sternly religious, and he lamented on God, Jesus, and the end times during his gospel concert tours. While some listeners dismiss these records altogether, that would be a terrible mistake, asShot of Lovewas more rooted in hard rock than gospel andfeatured one of Dylan’s true masterpieceswith its beautiful closing song, “Every Grain of Sand.”
2Good As I Been To You (1992)
Bob Dylan’s twenty-eighth studio album
Bob Dylan went through some creative difficulties during the 1980s and 1990sas he struggled to maintain his relevance and increasingly felt like a relic from a bygone era. However, Dylan returned to his folk roots with the astounding covers albumGood as I Been to You, a record that was comprised of traditional folk songs and was his first entirely acoustic record since 1964. This underrated, back-to-basics approach creatively renewed Dylan as he reconnected with his past and geared up to reinvent himself once again with his later, far more acclaimed comeback record,Time Out of Mind,in 1997.
Bob Dylan followed upGood as I Been to Youwith a second album of traditional folk covers,World Gone Wrong(1993.)
1"Love And Theft" (2001)
Bob Dylan’s thirty-first studio album
While most Bob Dylan enthusiasts will point toTime Out of Mindas the dawning of a new era as he debuted a more grizzled, aged, and bluesy voice, it’s important that his follow-up,“Love and Theft,”doesn’t get left behind in this discussion.Released on August 01, 2025, it’s not surprising that Dylan’s first 21st-century record is so slept on, as the attacks on the World Trade Center overshadowed its promotional period. However, looking back, it’s clear that this was some of Dylan’s most accomplished work and one of the most underrated albums he ever made.
Tracks like “Mississippi” and “Summer Days” showcased Dylan as an accomplished bluesman willing to share his aged wisdom.
While general listeners imagine the youthful, sunglasses-wearing Dylan of the 1960s when they think of this iconic musician, the songwriting on“Love and Theft”proved he could still deliver poetic masterpieces as he inched toward his twilight years. Tracks like “Mississippi” and “Summer Days” showcased Dylan as an accomplished bluesman willing to share his aged wisdom and have a rocking time while he did it. While everyone will have a different opinion onBob Dylan’smost underrated record, no self-respecting fan can deny that“Love and Theft”deserves to be a much bigger part of his legacy.
