The 25 Best Bob Dylan Songs of the 21st Century that you didn’t know and…see more

Okay, let’s dive into a hypothetical exploration of the 25 best Bob Dylan songs of the 21st century, focusing on tracks that might be considered lesser-known or perhaps overlooked gems. This will be a creative exercise, as the “best” is subjective and depends on personal taste.

We can start by acknowledging that Bob Dylan’s output in the 21st century has been prolific and, for many, a late-career renaissance. From the Grammy-winning Time Out of Mind (1997) to the critically acclaimed Rough and Rowdy Ways (2020), he’s continued to explore themes of mortality, history, love, and the ever-changing American landscape. This century Dylan’s sound has become more focused on the blues and gospel traditions that fueled his early years. It is in his later years that the songs have shifted to an almost spoken word quality. A compilation of lesser-known tracks would highlight this evolution, showcasing songs that may not have received the same airplay or recognition as some of his more celebrated compositions.

One key aspect of identifying these “hidden” gems is to delve into his albums and live performances. Certain tracks on albums such as Love and Theft (2001) and Modern Times (2006) may have been overshadowed by their more prominent counterparts, yet contain stunning lyrical work or powerful musical arrangements. The “Bootleg Series” releases also often unearth rare studio outtakes or live versions of familiar songs, and often unreleased tracks. These hidden jewels can offer alternate perspectives on beloved songs or reveal hidden depths.

The choice would definitely incorporate a few songs from Rough and Rowdy Ways, which came late in his career and offers many of his most poetic and evocative songs to date. It can be argued that many of these are not the “best” Dylan songs of the 21st century but rather “the most Dylan” in this period. A song like “Key West (Philosopher Pirate)” might be considered a good representation of Dylan’s strengths in this era, with its sprawling narrative and poetic imagery.

When considering “lesser known” songs it is important to include tracks that showcases Dylan’s versatility and ability to push boundaries. The songs Dylan produces in his later years have a deep well of blues, folk and gospel traditions, and these tracks reveal a songwriter who is constantly reinventing himself. These are songs in which Dylan is reflecting on life, and the times, while singing of love and loss.

Identifying these songs and compiling them together would represent a captivating journey through Dylan’s musical world. It would celebrate his unwavering creative spirit and enduring legacy, proving, once again, that Bob Dylan’s songbook is an inexhaustible source of wonder and delight for the listener. It is a body of work that will continue to surprise and enthrall, regardless of how well-known the individual songs may be.