The 20 Best Bob Dylan Songs From the 21st Century

At the time of this writing, Bob Dylan has released 40 studio albums, 10 of which have arrived in the 21st century.

It’s true that most of Dylan’s most popular and commercially successful songs come from albums released decades ago — tracks like “Blowin’ in the Wind,” “Like a Rolling Stone” and “Tangled Up in Blue” — but from the year 2000 to present day, Dylan has written dozens upon dozens of songs, not to mention covered a variety of Great American Songbook standards and reinterpreted his own material.

And people are still very much listening. In 2020, Dylan landed his first ever No. 1 song on any Billboard chart with the 17-minute “Murder Most Foul.”

Below, we’ve ranked The 20 Best Bob Dylan Songs From the 21st Century. For the purposes of this list, we’re sticking to studio albums only, though there is also plenty of good stuff to be found on Dylan’s live albums and bootleg releases.

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

Dylan had several early musical influences, and Hank Williams was most certainly one of them. “I became aware that in Hank’s recorded songs were the archetype rules of poetic songwriting,” he wrote in his memoir Chronicles: Volume One. “The architectural forms are like marble pillars.” In 2001, Dylan’s cover of “I Can’t Get You Off of My Mind” served as the leading track to Timeless: Tribute to Hank Williams.

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

Dylan singularly wrote every song on 2012’s Tempest with the exception of “Duquesne Whistle,” which he co-wrote with Robert Hunter, who was best known for his collaborations with the Grateful Dead. “Hunter is an old buddy,” Dylan told Rolling Stone back in 2009. “We could probably write a hundred songs together if we thought it was important or the right reasons were there. He’s got a way with words and I do too. We both write a different type of song than what passes today for songwriting.”

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

Dylan was not the first major rock artist to dip backward into the Great American Songbook, but one could argue he was one of the most dedicated to covering its material. Fallen Angels was the second of these releases, and it earned him a Grammy nomination for Best Traditional Pop Vocal Album. “Melancholy Mood” is a strong vocal performance on top of a polished arrangement.

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

Bob Dylan and Christmas music are not exactly phrases that go together — especially considering Dylan was born and raised Jewish — but one need only hear the song and watch the music video for “Must Be Santa” to hear the joy and whimsy of this project. Who’s got a beard that’s long and white? Santa Claus. Who’s got a top hat and a strange gray wig? Dylan in the below video.

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

Robert Hunter co-wrote most of the songs on Dylan’s 2009 album Together Through Life, a partnership that clearly worked well for both men. “When writing for Dylan, I hear Dylan’s voice,” Hunter explained to Highway 81 Revisited in 2014. “I write words that I can hear coming out of his mouth. Maybe not what he thinks, but things that would sound good with a Dylan voice on them.” David Hildago added accordion to “Beyond Here Lies Nothin,'” a part that’s both subtle and totally necessary.

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

As Dylan once famously said of his songs, “it used to go like that, and now it goes like this.” He said that in 1966, but it was an artistic sentiment that has continued for decades — Dylan is constantly reimagining his own work. One of the strongest displays of this was in 2023’s Shadow Kingdom, a collection of re-recordings of songs from the first half of Dylan’s career. The below version of “I’ll Be Your Baby Tonight” is much more rambunctious than the 1967 original.

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

We understand that not everyone is keen on hearing three album’s worth of standard covers by Dylan, which comes out to around 95 minutes of listening time. (To be fair though, Triplicate did earn a Grammy nomination for Best Traditional Pop Vocal Album and it went to No. 37 in the U.S.) But there are undoubtedly some worthy tracks, such as the classic “P.S. I Love You.”

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

As its title suggests, “High Water (For Charley Patton)” is a tribute to the late bluesman, though its not exactly a blues song itself. It leans on a jangly banjo part, courtesy of Larry Campbell, and some strong percussion work by David Kemper. “High Water” is ultimately a song about American history, the good, bad and ugly parts of it. “The album deals with power, wealth, knowledge and salvation,” Dylan said to Rolling Stone in 2001, themes that still carry a great deal of relevance and resonance 20 years later.

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

Plenty of jokes have been made about Dylan’s singing voice over the years, and Tempest is certainly not his clearest or easiest to listen to in that vein. But the lyrical content of “Pay in Blood” makes up for it. Take Elvis Costello‘s word for it, too. Back in 2011, Dylan showed Costello the lyrics to the song at a festival they were both playing at. Each chorus line, Costello later recalled (“I pay in blood, but not my own“), “was delivered with a different flourish: a swashbuckler’s panache, a black comical riposte, held with a steady gaze, tossed away with a wicked laugh or a ghost of a smile.”

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

That’s Mike Campbell of Tom Petty and the Heartbreakers playing the guitar solos on “I Feel a Change Comin’ On.” “He is Mr. Contraire Dylan,” Campbell said of working with the legend to Noise11.com in 2020. “I can tell you stories of how quirky and beautifully genius he is and how he interacts with people. … He is also a twitchy, goofy little kid with music. He gets into it on a high school level in a garage band. He is Bob Dylan, but he is one of us.”

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

Countless people have recorded covers of “Autumn Leaves,” but it was Frank Sinatra’s version that stuck in Dylan’s thoughts when he put his own spin on it for 2015’s Shadows in the Night, an album that included lots of songs Sinatra sang over the years. “When you start doing these songs, Frank’s got to be on your mind. Because he is the mountain. That’s the mountain you have to climb, even if you only get part of the way there,” Dylan explained to AARP: The Magazine then. “He had this ability to get inside of the song in a sort of a conversational way. Frank sang to you — not at you.”

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

If “Mississippi” sounds a bit like it belongs on 1997’s Time Out of Mind, that’s because it was recorded during those sessions, but did not find a place until Love and Theft. The version below was re-recorded specifically for the 2001 album. “I would love to put certain things on [an album], I just don’t think they were recorded right,” Dylan said at a press conference in 2001. “[‘Mississippi’] wasn’t recorded particularly well, and thank God it never got out, so we went and re-recorded it again. But something like that would never have happened 10 years ago. You’d have probably all heard the trashed version of it and I would have never re-recorded it.”

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

Bob Dylan namedropping Alicia Keys in the opening track to one of his albums? It’s more likely than you’d think. The opening few bars of “Thunder on the Mountain,” the leadoff song to 2006’s Modern Times, sets the tone for the rest of the LP, and yes, mentions Ms. Keys. It’s a strange yet fitting instance of Dylan being quite aware of contemporary figures in music, placed against a backdrop of blues and rockabilly.

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

The 1966 version of “Pledging My Time” from Blonde on Blonde has similarities with the 2023 version Dylan recorded of it for Shadow Kingdom — a harmonica part, the 12-bar blues structure. And yet, it’s an entirely different song, sung by a man many decades older and presumably wiser. Lines like “Everybody’s gone but me and you / And I can’t be the last to leave” strike differently.

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

Only Bob Dylan would randomly drop an astounding 17-minute song about the assassination of JFK in the middle of a global pandemic: “Murder Most Foul.” “Greetings to my fans and followers with gratitude for all your support and loyalty across the years,” he said on social media on March 27, 2020. “This is an unreleased song we recorded a while back that you might find interesting. Stay safe, stay observant and may God be with you.”

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

Dylan won the Nobel Prize in Literature in 2016, the same year he released his second album of standard covers, Fallen Angels. For someone so lauded for his writing, it’s interesting to hear Dylan tackle songs that did not bear the fruit of his own pen. It was freeing for him, in a way. “There’s enough of my personality written into the lyrics so that I could just focus on the melodies within the arrangements,” he told Bill Flanagan in a 2017 interview.

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

In 2018, Dylan contributed to an album called Universal Love – Wedding Songs Reimagined, in which gender-specific lyrics were adjusted so that they became same-sex love songs. So, for example, Dylan’s beautifully tender version of “She’s Funny That Way” became “He’s Funny That Way.” Dylan does not speak often about sexuality, his own or anyone else’s, but it’s not something he hasn’t considered. “Sex and love have nothing to do with female and male,” he said in 1966. “It is just whatever two souls happen to be.”

3. “Things Have Changed”
From: 2000 Single

With “Things Have Changed,” Dylan snagged both an Academy Award for Best Original Song and a Golden Globe Award for Best Original Song. (It appeared in the 2000 film Wonder Boys, starring Michael Douglas.) It’s ominous and yet waggish, sinister and seductive “All the truth in the world adds up to one big lie,” Dylan sings. If that ain’t the truth…

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

“I didn’t feel limited this time,” Dylan said to Rolling Stone in 2006, referring to his album Modern Times, “or I felt limited in the way that you want to narrow your scope down, you don’t want to muddle things up, you want every line to be clear and every line to be purposeful. … I just let the lyrics go, and when I was singing them, they seemed to have an ancient presence.” This is brilliantly displayed in “Beyond the Horizon,” with lines like “Beyond the horizon o’er the treacherous sea / I still can’t believe that you have set aside your love for me.”

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

There is much to like about 2020’s Rough and Rowdy Ways, but if there is one song from the album that perhaps best embodies Dylan’s puckish yet meaningful style of lyricism, it’s “Goodbye Jimmy Reed,” a fitting tribute to the blues legend. Here, sex and sin live on the same street as fame, God and “old time religion.” Former president Barack Obama named it one of his favorite songs of the entire year.