Best Bob Dylan songs from Time Out of Mind to Rough and Rowdy Ways

Last updated on February 18th, 2022 at 10:07 pm

Our hometown hero has done it again.

With his latest album Rough and Rowdy Ways, Bob Dylan is the first artist to have a top 40 album of original material in every decade since the 1960s. Which makes one wonder: how did any of his 80s albums chart that high? I kid, I kid. As a Dylan junkie, I even love Knocked Out Loaded and Down in the Groove, his only two 80s albums that didn’t crack the top 40.

Dylan’s late-era renaissance began with 1997’s Time out of Mind, and continues even up to Rough and Rowdy Ways. Sure, he released five albums worth of Sinatra material (and other stuff from the Great American Songbook), but those songs needed uncovering anyway. 

Not acquainted with the Minnesota bard’s most recent work? Here’s a 10-song playlist to get you started (plus 10 honorable mentions). And yes, I’m only counting original material. Sorry, Old Blue Eyes.

As far as the order goes, it’s structured to be a coherent playlist, so the best songs aren’t necessarily first. You can check out the playlist here.

“Things Have Changed” (from 2000 soundtrack to the film The Wonder Boys)

As far as fun, catchy late-era Dylan goes, “Things Have Changed” is #1. It’s also a great way to start off a playlist. “People are crazy and times are strange/I’m locked in tight/I’m out of range/I used to care/but things have changed.” Indeed, Bob, indeed. 

“Beyond Here Lies Nothing” (from the 2009 album Together Through Life)

2009’s Together Through Life is rightly seen as the weakest album in Dylan’s recent renaissance. That being said, it’s still a solid collection of songs. It’s just a little looser and less serious than the rest of his newer material, which isn’t always a bad thing. 

In fact, Together Through Life almost completely lacks pretense. There are no 14-minute songs about the Titanic, no 17-minute songs about the assassination of JFK, no apocalyptic tracks like “Ain’t Talking” from Modern Times. TTL finds Dylan entrenched in the folk tradition, borrowing lines, verses, and complete song structures from classic blues and country songs even more freely than he usually does.

The most original song on Together Through Life is also its best, “Beyond Here Lies Nothing.” It downright swings, although it isn’t without its darker side: “beyond here lies nothing/but the mountains of the past.” 

“High Water (For Charley Patton) (from the 2002 album “Love and Theft”)

It’s songs like “High Water” that make the rest of Dylan’s later albums so much more substantial than Together Through Life. This homage to Charley Patton, the greatest classic bluesman that you’ve never heard of, brings you back to the 1930s in the best possible way. 

“Red River Shore” (outtake from 1997’s Time Out of Mind)

Not only is “Red River Shore” one of Dylan’s best songs from this era, it is one of his best songs period. The mysterious, poignant ballad contains multitudes (see what I did there?). Bafflingly, it was left off of Time out of Mind, putting it in a pretty great group of other outtakes that are among his best material, including “Blind Willie McTell,” “Every Grain of Sand,” and “I’m Not There.” 

“Nettie Moore” (from the 2006 album Modern Times)

Since it’s so new, it isn’t easy to place Dylan’s latest album, Rough and Rowdy Ways, in his overall legacy. It’s tough to think that it’ll be more highly regarded than Time Out of Mind and Modern Times, both of which are classics. “Nettie Moore” is one of many highlights from the latter. Dylan goes full-on Americana, weaving lines and themes from a myriad of classic folk, blues, and country songs into an affecting whole. The chorus is surprisingly melodic. The first time he hits the final note of the line “oh, I miss you Nettie Moore/and my happiness is o’er” will give you chills.

“Love Sick” (from the 1997 album Time out of Mind)

This song has gone such a radical transformation in Dylan’s live shows that I forgot how mellow the studio version is. The circus organ is the bedrock of its haunting feel. 

“Roll on John” (from the 2012 album Tempest)

Like Together Through Life, Tempest is sometimes not as highly regarded by Dylan fans. It doesn’t quite have the sweeping grandeur of Time out of Mind, Modern Times, or Rough and Rowdy Ways.

That being said, there are a handful of songs from Tempest that could have made this list (see the honorable mentions). I chose “Roll on John,” Dylan’s tribute to John Lennon, because it’s just so moving to hear him talk about his old friend. The lyrics also point toward the approach he took on Tempest that he also used on Rough and Rowdy Ways, combining the serious and flippant in a way that legitimizes both.

“Not Dark Yet” (from the 1997 album Time out of Mind)

I could have chosen this song simply for the tag line of the chorus: “it’s not dark yet/but it’s getting there.” They say that the best songwriters/poets/etc. are prophets, and if that’s true, a strong case can be made that Dylan fits the bill. The feel of “Not Dark Yet” fits the lyrics perfectly. 

“Key West (Philosopher Pirate)” (from the 2020 album Rough and Rowdy Ways)

Contrary to popular belief, Bob Dylan can write beautiful songs. He’s also a great singer. “Key West (Philosopher Pirate)” is one of many examples that both things are true. Like a large amount of Rough and Rowdy Ways, its sparse and intimate instrumentation is simply gorgeous. The mystic backing vocals of Fiona Apple are especially affecting. 

“Murder Most Foul” (from the 2020 album Rough and Rowdy Ways)

When music historians look back on this era of Bob Dylan, I predict that they’ll see “Murder Most Foul” as his magnum opus. In fact, it might be the magnum opus of his entire career. The combination of seriousness and flippancy that gives “Roll on John” and “Tempest” their charm is taken to its full potential here. The lyrics are the story of the 60s, the story of America since then, the story of the longing in all of our hearts. 

Honorable mentions

Click here for a playlist of the honorable mentions.

“False Prophet” and “Goodbye Jimmy Reed” (from the 2020 album Rough and Rowdy Ways)

There’s more than just beautiful, intimate songs on Rough and Rowdy Ways. Like all of his recent albums, Dylan includes some upbeat jump blues, including these two highlights.

“Duquesne Whistle” and “Early Roman Kings” (from the 2012 album Tempest)

It almost seems like Dylan was going for songs that would be fun to play live on Tempest. Many still fill his set lists, including fun, catchy “Duquesne Whistle” and “Early Roman Kings.” 

“Thunder on the Mountain” and “Ain’t Talking” (from the 2006 album Modern Times)

The opening and closing tracks on Modern Times are the perfect bookends: the first, a swinging blues with prophetic undertones, the second, a dark, apocalyptic warning.

“’Cross the Green Mountain” (from the soundtrack to the film Gods and Generals)

The historian in Dylan comes out in this one, an 8-minute epic from Civil War film Gods and Generals. Side note: his hair looks awesome in the video.

“Mississippi” (from the 2001 album “Love and Theft”)

Dylan loved this song so much that he recorded like twelve versions of it (three appear on outtake collection Tell Tale Signs). Sheryl Crow also covered it. They’re all good, but the released version gets to the heart of this authentic blues.

“Make You Feel My Love” and “Cold Irons Bound” (from the 1997 album Time out of Mind)

“Make You Feel My Love” has been successfully covered by Billy Joel, Garth Brooks, and Adele – how’s that for good company? As always (with the notable exception of Hendrix’s “All Along the Watchtower”), Dylan’s version is the best, though. “Cold Irons Bound” won a Grammy, so I figured I had to at least mention it. I mean, it’s also a classic, so there’s that.