Bob Dylan: Favorite songs from each album of the ’00s (WITH VIDEOS)

bob dylan '00s



In honor of Bob Dylan’s 80th birthday, which was on May 24, I have been sharing a song from each of his albums — one song per day in chronological order — on Facebook, as I’ve done before for Elvis Costello, Lou Reed and Stevie Wonder. And I will collect them here, adding them after posting to Facebook.

I will include tracks from some (but probably not all) of Dylan’s compilations, live albums, soundtracks, side projects and so on, so I will probably have close to 100 entries when I am done.

Since Dylan’s output has been so prodigious, I am doing different blog posts for every decade, and linking them to each other.

(Update: Here are the posts for the ’60s, ’70s, ’80s’90s and ’10s (and beyond). And here is an index for all 77 songs in the series.)

After a very uneven output in the ’90s, Dylan started out the next decade strong, with “Things Have Changed,” which was included on (and written for) the soundtrack of the 2000 Michael Douglas movie, “Wonder Boys.” The narrator of the song may be world-weary, but the writing is sharp-edged and full of surprises. “I hurt easy, I just don’t show it/You can hurt someone and not even know it/The next 60 seconds could be like an eternity,” sings Dylan. “Gonna get lowdown, gonna fly high/All the truth in the world adds up to one big lie/I’m love with a woman who don’t even appeal to me.”

Four years after the excellent Time Out of Mind came the even better “Love and Theft” — the best album, I believe, of the second half of Dylan’s career. Though often wistful and melancholy, the album peaks with the raucous neo-rockabilly song “Summer Days,” bursting with musical energy and memorable lyrics: “I’m drivin’ in the flats in a Cadillac car/The girls all say, ‘You’re a worn out star’/My pockets are loaded and I’m spending every dime/How can you say you love someone else? You know it’s me all the time,” Dylan sings.

Dylan’s cover of “Red Cadillac and a Black Moustache” — co-written by Lilian May and Willie Bea Thompson and recorded by Warren Smith and others — was one of the highlights of the star-studded 2001 compilation album Good Rockin’ Tonight: The Legacy of Sun Records, which also featured tracks by Paul McCartney, Elton John, Eric Clapon and others.

The fifth volume of Dylan’s “Bootleg Series,” released in 2002, was devoted to November and December 1975 shows of Dylan’s Rolling Thunder Revue. Check out “The Lonesome Death of Hattie Carroll,” the protest song from 1964’s The Times They Are a-Changin’, given a new arrangement that makes it sound like it belongs on the Desire album.

” ‘Cross the Green Mountain,” which was included on the soundtrack of the 2003 Civil War movie “Gods and Generals,” is prime Dylan. It’s a far more lyrically complex cousin to “Knockin’ on Heaven’s Door” — a slow, somber, eight-minute look at the thoughts of a noble soldier facing imminent death. “Pride will vanish and glory will rot/But virtue lives and cannot be forgot,” Dylan sings.

Vol. 6 of Dylan’s “Bootleg Series,” released in 2004, documented his Halloween 1964 concert at Philharmonic Hall in New York, a solo concert except for four songs with Joan Baez. Dylan has performed the playful “If You Gotta Go, Go Now (Or Else You Got to Stay All Night),” an outtake from the Bringing It All Back Home sessions, only nine times in his career (all in 1964 and 1965), and this set includes one of them. (Philharmonic Hall, part of Lincoln Center, was renamed Avery Fisher Hall in 1973 and is now known as David Geffen Hall.)

The Bootleg Series, Vol. 7: No Direction Home: The Soundtrack (2005) featured some material from the Martin Scorsese-directed Dylan documentary “No Direction Home” and some other stuff as well. Among the highlights was an alternate version of Highway 61 Revisited‘s “It Takes a Lot to Laugh, It Takes a Train to Cry” with slightly different lyrics, a funkier beat, a looser overall feel and some dazzling guitar work from Michael Bloomfield.

Dylan confesses to an obsession with Alicia Keys and claims to have “sucked the milk out of a thousand cows” in “Thunder on the Mountain,” the rollicking opening track of Modern Times (2006). This is a song that manages to be both grandly mythical and deeply quirky. “The hammer’s on the table, the pitchfork’s on the shelf/For the love of God, you ought to take pity on yourself,” he sings as it ends.

The soundtrack of the Dylan-inspired 2007 movie “I’m Not There” included a stunning bonus: the previously unreleased title track, recorded during the “Basement Tapes” sessions of 1967 (with The Band). Sumptuous music, passionate singing, and lyrics that are a little confusing at first but gain clarity and impact in the song’s final few verses. Truly an unearthed masterpiece.

The two-CD 2008 set The Bootleg Series Vol. 8: Tell Tale Signs: Rare and Unreleased 1989-2006 features outtakes, alternate takes and rarities from that 17-year span, and offers abundant proof of the strength of Dylan’s songwriting during that time. One of the highlights is “Red River Shore,” an epic ode to the girl who got away that was recorded during sessions for the Time Out of Mind album but not included on it.

Dylan’s three studio albums between 1997 and 2006 — Time Out of Mind, “Love and Theft” and Modern Times — were all excellent, but the streak ended with 2009’s Together Through Life, which suffered from uninspired songwriting (mostly done in collaboration with Grateful Dead lyricist Robert Hunter) and singing so rough-edged it became distracting. It’s hard to find a song to wholeheartedly recommend here, but I’ll go with “If You Ever Go to Houston.”

I’m not saying it was a great idea for Dylan to release a holiday album, Christmas in the Heart, in 2009. And I’m not saying that the album is a masterpiece or anything. But I do love its “Must Be Santa” (though it must be added that Brave Combo came up with the arrangement and the idea of adding the presidents’ names).


Since launching in September 2014,, a 501(c)(3) organization, has become one of the most important media outlets for the Garden State arts scene. And it has always offered its content without a subscription fee, or a paywall. Its continued existence depends on support from members of that scene, and the state’s arts lovers. Please consider making a contribution of any amount to via PayPal, or by sending a check made out to to 11 Skytop Terrace, Montclair, NJ 07043.


Custom Amount

Personal Info

Donation Total: $20.00

Explore more articles:

Leave a Comment

Sign up for our Newsletter