Happy 50th birthday to Highway 61 Revisited, Bob Dylan‘s strangest, funniest, most baffling and most perfect album. Released on August 30th, 1965, it arrived just five months after his previous masterpiece, Bringing It All Back Home, but this was a different guy making a different album, a folk rogue embracing the weirdness and spook of electric rock & roll. “The songs on this specific record are not so much songs but rather exercises in tonal breath control,” Dylan explains in his wonderfully insane liner notes. “The subject matter — tho meaningless as it is — has something to do with the beautiful strangers.” And that’s what the nine songs on Highway 61 add up to: a late-night road trip through an America full of beautiful strangers who’ll never get back home.
Highway 61 is the middle album in the trilogy of Bringing It All Back Home and Blonde on Blonde—from that moment when Dylan flipped for the Beatles, went electric and banged out these three rock & roll albums in the space of 14 manic months, three albums everybody (including Dylan) has been trying to live up to (or just plain imitate) ever since. All three have different flavors — if Bringing It All Back Home takes off from the Beatles, Highway 61 is the Stones and Blonde on Blonde is Smokey Robinson — but unlike the other two, Highway 61 never lets up. This album has no “On the Road Again” or “Obviously Five Believers” — a moment of pleasant filler where you can catch your breath. Each of the nine songs tells its own immaculately frightful story.
And more than Bringing It All Back Home, Highway 61 is a band album, rather than a solo album. The songs are juiced with perfect moments of musical interaction — Charlie McCoy’s guitar on “Desolation Row,” Paul Griffin’s piano on “Just Like Tom Thumb’s Blues,” Bobby Gregg’s drums on “It Takes a Lot to Laugh, It Takes a Train to Cry,” Michael Bloomfield’s twang in “Tombstone Blues,” everybody and everything on “Ballad of a Thin Man.” Even the infamously out-of-tune guitar on “Queen Jane Approximately” adds to the spirit.
I first heard “Like a Rolling Stone” on the radio as a little kid in the Seventies, on a short-lived Boston Top 40 AM station called WACQ — the voice so threatening, so disturbing, sneering like the Fonz, except also a cool voice that would make anyone itch to join the wild adventure he was singing about. He did that trademark Dylan move of changing his mind about the lyrics in the middle of a word — “To be haaaa-on your own!” (And to think some people still trust this man’s lyric sheets.) How did he get away with that? It was a voice like nothing else I’d ever heard. Then the DJ segued right from “Like a Rolling Stone” to the disco hit “Heaven on the Seventh Floor,” about getting stuck in an elevator with a foxy lady. Hard to believe that station went out of business.
I spent so much of my teen years trying to decipher those liner notes and that Daniel Kramer cover photo. Dylan stares out at the camera in Jewish-cowboy mode, Paul Newman–style, with mystery-tramp eyes that seem to ask, “Do you want to make a deal?” Behind him, a girl in a Creamsicle-striped T-shirt stands with her camera, impatiently waiting for him to take her out for a ride. (The girl was actually a boy — Dylan pal Bob Neuwirth, whose gender-neutral crotch adds a lot to the cover’s power.) The photo captures the restless let’s-gooo vibe at the start of a road trip, a vibe that lasts about halfway through the first verse of “Like a Rolling Stone,” which is where the trip gets weird. You can still feel Dylan’s eyes on you through the album, his head tilted at that curious angle — what, you thought this ride was going to be fun or something?
Somehow, with so much poetic imagery on one album, the most haunting line is one of the simplest — that moment in “It Takes a Lot to Laugh” when Dylan drawls, “I been up all night, leaning on the windowsill.” The whole album is a windowsill the world has been leaning on for 50 years — these songs are magnificently bleak company for staying up and brooding all night. And listening to Highway 61 now, it’s hard to believe the guy who sings these songs has gotten a night’s sleep since.
It’s an album that begins with a warning to pawn your diamond ring and save your dimes and keep track of all the people you fucked over yesterday, because they’re the same people you’ll be begging for hand-outs tomorrow. But it’s also an album that ends with a man signing off a letter telling you that he’s seen too much depravity in the city to read any more of your letters from home. (“When you asked how I was doing, was that some kind of joke?”) The album begins by laughing at a stuck-up young kid who never thought she’d wind up on Desolation Row; it ends with a no-longer-young kid who’s given up hope he’ll ever get out. The album begins by mourning all the two-bit friends you met in the big city who ripped you off for drugs and sex and money, the “beautiful strangers” who turned out to be Not Your Friends; the album ends by cheerfully promising that you can’t go back home to your old friends or family either.
But all the wintertime-is-coming nightmares on this album coexist with Dylan’s wildest, most generous comedy. It’s the most compassionate album he ever made, because it’s the album where he finds every American he meets hilarious. There isn’t any moral condemnation, which must be unique for a Sixties Dylan album — even his enemies, the lepers and crooks promoting our next world war, crack him up. His empathy for Queen Jane’s midlife blues must have been shocking in 1965, as if it isn’t now; he takes her side against her resentful children. Queen Jane and Mr. Jones could be Miss Lonely’s parents. (Or Queen Jane might be the badass Second Mother who runs off with the Seventh Son.)
“It’s the most compassionate album Dylan ever made, because it’s the album where he finds every American he meets hilarious.”
People might have heard “Ballad of a Thin Man” as a denunciation of Mr. Jones, but Dylan is singing too deeply for that — the ghostly “whooooa-oooow” he lets out at the end isn’t the kind of sound you make in a song about somebody else’s problems. Dylan feels Mr. Jones because every local loser on this highway — every American — has a little of Mr. Jones’ confusion in them. And none of them really knows what’s happening, although it’s a tribute to Dylan’s genius that his voice still makes you suspect he’s got the secret tucked away in his boot.
If there’s one song that’s grown the most over the years, it’s “Just Like Tom Thumb’s Blues,” where Dylan strikes an impossibly friendly tone even as he sings about total devastation, stuck on the long road between Juarez and New York City (2,178 miles!), where it’s just one loser after another. Dylan vows to head back to where he came from, even though he knows the NYC he left won’t be there anymore. It’s a sad song that nonetheless makes you smile wherever you encounter it — sampled brilliantly by the Beastie Boys on Check Your Head, or banged out by the Grateful Dead, with Phil Lesh mangling the lyrics from “my best friend the drummer won’t even tell me what it is I dropped” to “I started out on Heineken but soon hit the harder stuff.”
I saw Dylan do “Tom Thumb’s Blues” at Madison Square Garden in November, 2001, right after 9/11, and the opening notes set off frenzied waves of joy throughout the crowd (“He’s doing that one! The ‘going back to New York City’ one!”), even though every character in the song is truly and utterly fucked. Dylan almost halfway cracked a smile as 20,000 people sang the punchline back at him. That wiseass compassion is why so many listeners keep hearing themselves in these songs. Even with all the danger and turmoil Dylan finds on this highway, the tears on his cheeks are from laughter.