As of now, Bob Dylan has an impressive discography featuring 40 studio albums, with 10 of those albums released in the vibrant 21st century. While it is well-documented that many of Dylan’s most acclaimed and commercially successful tracks were produced in earlier decades—such as iconic songs like “Blowin’ in the Wind,” “Like a Rolling Stone,” and “Tangled Up in Blue”—he has continued to be prolific. From 2000 to the present, Dylan has penned an extensive collection of new songs, alongside delivering unique takes on various classics from the Great American Songbook and revisiting his own timeless pieces.

His enduring appeal is evident, as in 2020, he achieved a significant milestone by securing his first-ever No. 1 song on any Billboard chart with the remarkable 17-minute track titled “Murder Most Foul.” This achievement underscores Dylan’s lasting impact and relevance in the music industry.

In the following sections, we present our curated list of The 20 Best Bob Dylan Songs From the 21st Century. For this selection, we will focus exclusively on tracks from his studio albums, while acknowledging that his live recordings and bootleg releases also contain a wealth of incredible material.

20. “I Can’t Get You Off of My Mind”
From: Timeless: Tribute to Hank Williams (2001)

Dylan’s early musical influences are numerous, with the legendary Hank Williams standing out prominently. In his memoir, Chronicles: Volume One, Dylan remarked, “I became aware that in Hank’s recorded songs were the archetype rules of poetic songwriting.” His cover of “I Can’t Get You Off of My Mind,” released in 2001 as the lead track for Timeless: Tribute to Hank Williams, showcases Dylan’s deep respect for this pioneer of country music. This song embodies the poetic structures that shaped Dylan’s songwriting journey.

19. “Duquesne Whistle”
From: Tempest (2012)

On the 2012 album Tempest, Bob Dylan penned every track himself, with the exception of “Duquesne Whistle,” a collaborative effort with Robert Hunter, famed for his work with the Grateful Dead. Dylan described Hunter as “an old buddy,” indicating the strong creative bond they share. In an interview with Rolling Stone, he expressed that their songwriting partnership could yield countless songs if the circumstances were right. Their collaborative style results in a unique blend of lyrical depth and musical innovation that resonates with listeners.

18. “Melancholy Mood”
From: Fallen Angels (2016)

While Dylan wasn’t the first prominent rock artist to explore the Great American Songbook, his dedication to this genre is noteworthy. Fallen Angels marks his second foray into this realm, earning him a Grammy nomination for Best Traditional Pop Vocal Album. The track “Melancholy Mood” features Dylan’s exceptional vocal delivery over a meticulously crafted arrangement, demonstrating his ability to breathe new life into classic standards while maintaining emotional authenticity.

17. “Must Be Santa”
From: Christmas in the Heart (2009)

Bob Dylan may not be the first name that comes to mind when one thinks of Christmas music, especially given his Jewish upbringing, yet his rendition of “Must Be Santa” radiates festive joy and whimsy. The accompanying music video captures the playful spirit of the holiday season. In this delightful track, Dylan’s interpretation showcases his unique style while embracing the traditional Christmas narrative, inviting listeners to experience the warmth and cheer that define this season.

16. “Beyond Here Lies Nothin’”
From: Together Through Life (2009)

Collaborative songwriting has been a hallmark of Dylan’s career, and his partnership with Robert Hunter on the 2009 album Together Through Life exemplifies this synergy. Hunter revealed that when crafting lyrics for Dylan, he envisions them being delivered in Dylan’s unmistakable voice. This creative process results in songs that capture the essence of Dylan’s stylistic nuances. The addition of David Hidalgo’s accordion on “Beyond Here Lies Nothin’” adds a subtle yet essential layer, enhancing the song’s emotional depth.

15. “I’ll Be Your Baby Tonight”
From: Shadow Kingdom (2023)

In a captivating reflection of his artistic evolution, Dylan remarked, “it used to go like that, and now it goes like this,” a sentiment he expressed in 1966 that remains ever-relevant. The 2023 release Shadow Kingdom features reimagined versions of his classic songs, showcasing his willingness to reinterpret his musical legacy. The rendition of “I’ll Be Your Baby Tonight” stands out for its exuberance compared to the original 1967 version, illustrating Dylan’s dynamic approach to his own work as he continues to grow as an artist.

14. “P.S. I Love You”
From: Triplicate (2017)

While not every fan may appreciate the lengthy three-album collection of standard covers featured in Triplicate, which totals around 95 minutes, there are certainly standout tracks within. The classic “P.S. I Love You” is a prime example, earning a Grammy nomination for Best Traditional Pop Vocal Album and achieving a respectable No. 37 on the U.S. charts. This song highlights Dylan’s ability to infuse his distinctive style into timeless love songs, even those not originally written by him.

13. “High Water (For Charley Patton)”
From: Love and Theft (2001)

The title of “High Water (For Charley Patton)” pays homage to the influential blues musician, yet the song transcends traditional blues elements. Featuring a captivating jangly banjo performance by Larry Campbell and compelling percussion by David Kemper, “High Water” tells a narrative that encapsulates various facets of American history, both the triumphs and the tragedies. Dylan poignantly articulated that the album explores “power, wealth, knowledge, and salvation,” themes that resonate deeply even two decades later.

12. “Pay in Blood”
From: Tempest (2012)

Throughout his career, Dylan’s distinctive singing voice has garnered its share of commentary, and Tempest showcases an intriguing vocal delivery. However, the lyrical prowess of “Pay in Blood” more than compensates for any vocal limitations. Elvis Costello, a fellow musician, recounted an experience at a festival where Dylan shared the lyrics with him. Each chorus line, with its various tones—ranging from swashbuckling bravado to dark humor—was delivered with a captivating intensity that showcases Dylan’s unique storytelling ability.

11. “I Feel a Change Comin’ On”
From: Together Through Life (2009)

In “I Feel a Change Comin’ On,” the guitar solos are masterfully executed by Mike Campbell of Tom Petty and the Heartbreakers. Reflecting on his collaboration with Dylan, Campbell described him as “Mr. Contraire Dylan,” highlighting the artist’s quirky genius and youthful enthusiasm for music. Campbell’s insights reveal the deep connection and collaborative spirit that define their working relationship, showcasing Dylan’s ability to engage with his craft on a personal and relatable level.

10. “Autumn Leaves”
From: Shadows in the Night (2015)

Many artists have put their own spin on “Autumn Leaves,” but it was Frank Sinatra’s iconic version that greatly influenced Dylan’s interpretation for 2015’s Shadows in the Night. This album features a collection of songs that Sinatra popularized, and Dylan acknowledged the challenge of approaching these timeless pieces. He noted, “Frank’s got to be on your mind. Because he is the mountain. That’s the mountain you have to climb.” Dylan’s version captures the essence of Sinatra’s emotional delivery, making it a memorable tribute to the classic tune.

9. “Mississippi”
From: Love and Theft (2001)

“Mississippi,” while reminiscent of the sessions for Dylan’s earlier album Time Out of Mind, found its rightful place on Love and Theft after being re-recorded specifically for this release. Dylan expressed his desire for the song to reflect his vision accurately, stating, “I just don’t think they were recorded right.” This meticulous attention to detail demonstrates Dylan’s commitment to ensuring his work resonates as he envisions it, which is a hallmark of his artistic integrity.

8. “Thunder on the Mountain”
From: Modern Times (2006)

In “Thunder on the Mountain,” the opening track from Modern Times, Bob Dylan cleverly references contemporary artist Alicia Keys, illustrating his awareness of the ever-changing landscape of music. The song sets a vibrant tone for the entire album, blending elements of blues and rockabilly while engaging with contemporary figures seamlessly. This fusion of styles showcases Dylan’s ability to remain relevant and connected to the modern musical landscape while honoring his roots.

7. “Pledging My Time”
From: Shadow Kingdom (2023)

Dylan’s 2023 rendition of “Pledging My Time” draws inspiration from the original 1966 version found on Blonde on Blonde, retaining elements like a harmonica part and a 12-bar blues structure. However, this new version is infused with the wisdom and experience of a much older artist. The poignant lines, such as “Everybody’s gone but me and you / And I can’t be the last to leave,” resonate with a depth that reflects the passage of time and personal growth, making it a compelling reimagining.

6. “Murder Most Foul”
From: Rough and Rowdy Ways (2020)

In an extraordinary artistic move, Bob Dylan released “Murder Most Foul,” a stunning 17-minute composition addressing the assassination of JFK amid a global pandemic. This song reflects Dylan’s unique ability to craft profound narratives that resonate with historical events and personal experiences. On March 27, 2020, he shared the track with his fans, remarking on the gratitude he feels for their support over the years. This release not only showcases Dylan’s lyrical brilliance but also serves as a poignant reflection on contemporary society.

5. “All or Nothing at All”
From: Fallen Angels (2016)

In 2016, the same year he received the prestigious Nobel Prize in Literature, Dylan released Fallen Angels, his second album filled with standard covers. This endeavor allows Dylan to explore melodies that are not his own creations while still infusing them with his trademark personality. In a 2017 interview, he expressed how liberating it was to focus on the melodies within the arrangements, demonstrating his adaptability and creativity as an artist.

4. “He’s Funny That Way”
From: Universal Love – Wedding Songs Reimagined (2018)

In 2018, Bob Dylan contributed to the album Universal Love – Wedding Songs Reimagined, where traditional gender-specific lyrics were transformed to celebrate same-sex love. Dylan’s rendition of “She’s Funny That Way” was reimagined as “He’s Funny That Way,” showcasing his willingness to adapt and embrace themes of love and identity. While Dylan rarely discusses sexuality openly, his thoughtful approach to these topics highlights his understanding of the fluidity of love, reinforcing the universality of human experience.

3. “Things Have Changed”
From: 2000 Single

“Things Have Changed,” a standout track that earned Dylan both an Academy Award and a Golden Globe for Best Original Song, encapsulates the artist’s ability to convey complex emotions. Featured in the film Wonder Boys, this song combines ominous and humorous elements, capturing the duality of human experience. Dylan’s poignant lyrics, including the line “All the truth in the world adds up to one big lie,” resonate deeply, serving as a stark reminder of the complexities of truth in our lives.

2. “Beyond the Horizon”
From: Modern Times (2006)

In an insightful reflection on his creative process, Dylan described feeling unconfined while working on Modern Times. He aimed to narrow his focus to create clarity and purpose in every line. This artistic freedom is beautifully showcased in “Beyond the Horizon,” where evocative lyrics such as “Beyond the horizon o’er the treacherous sea / I still can’t believe that you have set aside your love for me” convey a sense of timeless longing and emotional depth that resonates with listeners across generations.

1. “Goodbye Jimmy Reed”
From: Rough and Rowdy Ways (2020)

Among the many standout tracks on Rough and Rowdy Ways, “Goodbye Jimmy Reed” perhaps best exemplifies Bob Dylan’s clever and meaningful lyricism. This song serves as a heartfelt tribute to blues legend Jimmy Reed, intertwining themes of desire, morality, fame, and spirituality. Former President Barack Obama recognized it as one of his favorite songs of the year, highlighting the cultural significance and emotional impact of Dylan’s music.