Bob Dylan Meets Miley Cyrus

I was having a latte at a coffee house the other day when a young female voice appeared on the house stereo, singing a ballad of love and loss that sounded vaguely familiar. It took a moment to realize the song was "You're Gonna Make Me Lonesome When You Go," and that it was originally written and sung by Bob Dylan on the 1975 album Blood on the Tracks, his vinyl saga of a painful marital breakup. This twentysomething sounded a bit young to have gone through that ordeal, but still, there was something fresh and wistful in her delivery, as if she could see ahead to future heartbreak.

I'll look for you in old Honolulu, San Francisco, Ashtabula

Yer gonna have to leave me now, I know

But I'll see you in the sky above

In the tall grass, in the ones I love

I was shocked when I clicked the Music ID app on my iPhone, and discovered that the singer was Miley Cyrus. That's right -- the former star of Disney's Hannah Montana TV series who recently graduated to too-revealing outfits and auto-tuned hits like "Party in the USA." How did she suddenly become so knowing, so profound, so Dylanesque?

That's the sort of mind-expanding effect Freewheelin' Bob long has had on his fans, and on his musical contemporaries, from the Turtles to Jimi Hendrix (whose cover of "All Along the Watchtower" is heard more often on rock radio than Dylan's own version). But a just-released compilation, Chimes of Freedom: The Songs of Bob Dylan Honoring 50 Years of Amnesty International, shows that Dylan continues to influence a generation of younger artists such as Cyrus, as well.

Dylan, who turns 71 in May, reportedly agreed to green-light the project on the condition that the producers open up the floodgates and allow more than just the usual Dylan acolytes to have a crack at covering his half-century of classic compositions. He apparently wanted people who didn't grow up hearing his music, who may have been familiar with him mostly as the old guy in the cowboy suit who strums a guitar in an iPod commercial. (I can't resist this aside: In Walter Isaacson's recent Steve Jobs bio, there's a fascinating inside account of how the perfectionistic Jobs -- despite being a fanatical Dylan fan who owned a massive library of concert bootlegs -- had the temerity to make the folk-rock icon reshoot the commercial because he didn't think the first version was good enough.)

The result: Chimes of Freedom is a fascinating, erratic but often brilliant melange of musical talents.

I would have expected 92-year-old folk icon and Dylan mentor Pete Seeger ("Forever Young") and Kris Kristofferson ("Quinn the Eskimo," a 1967 Dylan composition made more famous by Manfred Mann). I also could have foreseen British folk rocker-activist Billy Bragg, who did his own CD of Dylan covers, The Dylan Side of Billy Bragg, a few years back, and whose clear-toned, unaffected acoustic version of "Lay Down Your Weary Tune" somehow sounds fresher and more earnest than Dylan's own 1964 version. I can say the same about country rocker-turned-actor Steve Earle's cover of "One More Cup of Coffee (Valley Below)," which is as brilliantly atmospheric and mysterious as Dylan's rendition on the 1976 album Desire.

And perhaps, given Dylan's popularity among reggae artists, I might have anticipated Ziggy Marley doing "Blowin' in the Wind." But what I wouldn't have expected is Marley's tense, edgy reworking of that classic, which will make you forget the Peter, Paul and Mary version forever. Marley's version brings to mind how Dylan might have sounded if he'd spent his formative years on the violent streets of a Jamaican shantytown neighborhood, instead of strumming guitar in a coffee house in Minneapolis's bohemian Dinkytown, where he first happened upon Woody Guthrie's memoir, Bound for Glory, and decided to reinvent himself with the Depression-era folksinger and hobo as a template.

It's a wonderful irony that younger artists are now reinventing themselves in the image of the man who was, in his own teens and twenties, a restless, protean poser. But somehow, Dylan's aura strips away Cyrus' glossy, commercial artificiality and brings out the talented country singer beneath it. Similarly, I never would have dreamed that Ke$ha, best known for singing about brushing her teeth with a swig of Jack Daniels, would even attempt "Don't Think Twice, It's All Right" (though after listening to her stumble through it, I'm tempted to say that she just kinda wasted my precious time).

In a Rolling Stone interview, Ke$ha says the potency of Dylan's lyrics penetrated her too-jaded veneer. "The emotion caught up with me and I just started weeping," she says. "It's something that I didn't plan on, that wasn't contrived at all. It just sort of happened."

Dylan long has shown an almost perverse pleasure in shocking his fan base and daring them to accompany him into discomforting new territory -- perhaps best illustrated by his infamous performance at the 1965 Newport Folk Festival, where he showed up with an electric band and proceeded to rock out -- to the consternation of the folkies who booed and screamed "Judas!" from the back rows. In the early 1980s, during his brief conversion to evangelical Christianity, I went to a concert in which he rebuffed fans' requests that he play the suddenly too-sinful "Lay Lady Lay," and instead taunted them by strumming the chords and suggesting that they sing the words instead of him.

In that respect, Chimes of Freedom is utterly true to Dylan's personality. In one sense, he's tweaking legions of loyal Dylan buffs by giving them a trippy instrumental performance of "Don't Think Twice" by Kronos Quartet, the avant-garde string ensemble. That cut is only marginally listenable, alas, but other Dylan-inspired experiments produce brilliant results. For example, the Tex-Mex version of "Love Sick" by Mariachi El Bronx is so weirdly wonderful that some movie director should make a Sergio Leone-style spaghetti western just so he can use it as the theme music.

The exotic choice of Dylan interpreters isn't just a novelty gimmick. It's a reminder that Dylan has exerted such a pervasive, potent influence on our generation's musical tastes -- and our way of looking at the world -- because he never allowed himself to become a complacent rock idol. Bob Dylan takes chances and tries all sorts of things. Sometimes the result is awful, but sometimes it's a brilliant, mind-bending breakthrough. That he's still inspiring musicians of all ages to kick-start the bike and roar down some strange, new road with him is just another sign of his genius.

From producers Jeff Ayeroff and Julie Yannatta, here's an interesting Huffington Post essay about their intent in making Chimes of Freedom, and how, in a play on a slogan by Dylan's inspiration, Woody Guthrie, "this album saves lives."

Related: Bob Dylan's Latest Incarnation as a Painter