17 Facts About Bob Dylan’s Enigmatic Career

He's been called the "voice of a generation," a sell out and perhaps most famous of all, a terrible singer. Take a deep dive into his enigmatic career.

17 Facts About Bob Dylan’s Enigmatic Career

bob dylan 1974 — Bob Dylan performs with The Band at the Forum in Los Angeles, February 1974.

Dylanologists maintain it's only a matter of time before every serious pop music fan comes around to herald the genius of Bob Dylan — and his coffers are counting on it.

The Nobel Prize-winning songwriter who went from Greenwich Village folkie to electrifying the burgeoning 1960s' counterculture with lyrics like "While money doesn't talk, it swears. Obscenity, who really cares. Propaganda, all is phony" has never pretended to be anything but a self-proclaimed "song and dance man" — out to ply his craft and make a living.

Yet music fans and critics can't resist labels. He's been called a mercurial genius, the "voice of a generation," a sell-out, a washed-up plagiarist, and perhaps most famous of all, a terrible singer.

Depending on your POV, Bob Dylan fits one, all, some or none of these labels. Welcome to the wild ride that's been Dylan's nearly six-decade career — one loaded with more twists and turns than the lyrics to "Tangled Up In Blue."

That'll Be the Day...Buddy Holly Looks Dylan in the Eye

bob dylan and buddy holly — Bob Dylan (left) in 1963 and his inspiration, Buddy Holly, in 1959. Dylan said of seeing Holly in concert: "He looked me straight dead in the eye, and he transmitted something."

Growing up in middle-class Hibbing, Minnesota, a teenage Bobby Zimmerman makes a fateful trip to see a Buddy Holly concert in Duluth, Minnesota. A ticket costs about $2.

The 1950s' rock pioneer makes such a profound impact on Dylan, he's mentioned the concert in his acceptance speeches for both the 1997 Album of the Year Grammy and 2016 Nobel Prize in Literature. In the latter, Dylan recalls a sort-of rock 'n' roll anointment he believes transpired while watching Holly on stage.

"He looked me straight dead in the eye, and he transmitted something. Something I didn't know what. And it gave me the chills," said Dylan in his Nobel Prize acceptance speech.

Holly dies in a plane crash three nights later. But the kid from Hibbing is just taking flight.

Bobby Zimmerman, Meet Bob Dylan

bob dylan guitar — Robert Zimmerman started calling himself Bob Dylan in 1959. Here he's shown performing in 1963.

A duck-tailed Bobby Zimmerman fronts his high-school garage band, the Golden Chords, who cover Little Richard songs as poodle skirts twirl at the future star's first-ever paying gig in Hibbing's National Guard Armory building.

In 1959, majoring in music at the University of Minnesota, Zimmerman begins calling himself Bob Dylan (inspired by poet Dylan Thomas). In a flash, he's also ditched sock hops in favor of strumming acoustic folk songs at local coffeehouses — his head buzzing with Beat poetry by Allen Ginsberg, Gregory Corso, Lawrence Ferlinghetti. Dylan bunks in a $30-per-month apartment above a drug store. His new musical hero is folk icon Woody Guthrie.

In his 2004 memoir "Chronicles Volume One," he says of the era, "I played morning, noon and night. That's all I did, usually fell asleep with the guitar in my hands."

Talkin' New York

bob dylan joan baez — Bob Dylan sings with fellow New York folk musician Joan Baez at the Civil Rights March on Washington, D.C. in 1963.

A penniless Dylan drops out of college and hitchhikes to New York City, where he dives deep into the Greenwich Village folk music scene of the early '60s.

In the song "Hard Times In New York Town," Dylan sings "If you got a lot o’ money you can make yourself merry. If you only got a nickel, it’s the Staten Island Ferry."

For raggedy Bob, it's the latter — a life of couch surfing, scraping a buck playing the folk-club circuit and poring through musty old books at the New York Public Library. Just ten months after arriving in town, Columbia Records talent scout John Hammond sees potential in the 20-year-old and inks him to a record deal.

From Pauper to "Pawn in Their Game"

Bob Dylan performs in his influential video for the song "Subterranean Homesick Blues" in 1965.

Bob Dylan's self-titled debut album is recorded for $402 and mostly contains folk cover songs. Upon the record's 1962 release, it flops. But sales and notoriety grow with Dylan's self-penned tunes on follow-up LPs like "The Freewheelin' Bob Dylan" and "Another Side of Bob Dylan."

Hot on their heels comes what's widely considered one of the most influential rock albums ever, "Bringing It All Back Home." Gone are Dylan's early so-called "protest" songs, replaced by the surreal, stream-of-consciousness lyrics to tunes like "Mr. Tambourine Man" and "Subterranean Homesick Blues." Dylan's folk-purist fans pitch a hissy fit. And if they think this stuff's weird, they ain't heard nothin' yet.

Dylan, Amplified

dylan goes electric — Dylan went electric at the Newport Folk Festival in 1965, changing popular music.

Dylan's signature song, "Like a Rolling Stone," made such an impact on a teenage Bruce Springsteen, in his 1988 speech inducting Dylan into the Rock and Roll Hall of Fame, he said the song "sounded like somebody'd kicked open the door to your mind."

In concert, Dylan swapping acoustic folk songs for electric rock was famously met by booing audience members at the 1965 Newport Folk Festival. But the clamor was quickly drowned out by cash registers ringing up big sales for the albums "Highway 61 Revisited" and "Blonde on Blonde."

The "Dylan goes electric" concert at Newport endures as a seminal moment in rock history. The Fender Stratocaster guitar Bob played that night is valued at nearly $1 million and currently on display at Chicago's American Writers Museum (through April 2019).

The 1970s: Dylan's Second Coming

bob dylan george harrison — Bob Dylan (right) performs with George Harrison during a benefit concert at Madison Square Garden in New York City, Aug. 1971.

The early '70s found Dylan, now a family man, trying to shake the labels he felt the counterculture had mistakenly bestowed upon him. In "Chronicles Volume One" he lists them as the "Big Bubba of Rebellion, High Priest of Protest, the Czar of Dissent, the Duke of Disobedience, Leader of the Freeloaders, Kaiser of Apostasy, Archbishop of Anarchy, the Big Cheese."

By decade's end, Dylan had raked in beaucoup bucks on a 1974 concert tour with The Band; released two of his most beloved albums ("Blood On The Tracks" and "Desire"); and bewildered fans yet again by becoming a born-again Christian and turning out gospel albums.

Dylan's Publishing Deal With the Devil

dylan 1965 — Bob Dylan, shown here in London in 1965, signed a bad contract with his early manager, Albert Grossman.

Back in 1962, at the start of Dylan's career, his manager Albert Grossman persuaded the naive songwriter to transfer publishing rights to his songs from Duchess Music to Warner Brothers' subsidiary Witmark and Sons. Unbeknownst to Dylan, Grossman had pre-negotiated a back-channel deal with Witmark that gave him fifty-percent publishing income on every song Bob wrote.

In the '60s, when acts from The Byrds to Jimi Hendrix were scoring hits with Dylan covers like "Mr. Tambourine Man" and "All Along The Watchtower," Grossman was grabbing cash hand over fist.

"Where's my money?" said The Joker to The Thief

Dylan 1981 — Bob Dylan performs at the Olympic Stadium in Colombes, France, before an estimated 40,000 fans, in 1981.

Dylan would fire Grossman in 1971, dissolve their contracts and ultimately go mano-a-mano in a 1980s' legal fight that was settled out of court, reportedly in Grossman's favor. Fans have long speculated the lyrics to the 1967 song "Dear Landlord" are about his ex-manager: "Please don't put a price on my soul. My burden is heavy, my dreams are beyond control."

He Nearly Called it Quits in the 1980s

petty dylan — Bob Dylan (right) performs with Tom Petty at Madison Square Garden in New York City in July 1986.

As Dylan recounts in “Chronicles Volume One,” by 1986 he'd hit the bottom of the creative barrel, writing "I felt done for, an empty-burned out wreck."

His latest album was the dreadful "Knocked Out Loaded," which Rolling Stone magazine called a "depressing affair." Uninspired and performing on autopilot during a co-headlining tour with Tom Petty and the Heartbreakers, Dylan decided he'd hang it up soon.

But first there was another paycheck to collect for a tour with the Grateful Dead. Taking a break from rehearsals in Northern California, Dylan was in a bar watching a live jazz trio. Focusing on the singer, he had an epiphany.

In “Chronicles Volume One,” Dylan recalls, "I could feel how he worked at getting his power, what he was doing to get at it. I knew where the power was coming from and it wasn’t his voice, though the voice brought me sharply back to myself."

And with that, the "Bobfather" would win back his mojo and mount a late-career comeback that no one saw coming.

The Never Ending Tour Begins...

Dylan Berlin — An East Berliner holds a self-made painting of Bob Dylan at an open-air-concert in Berlin, Germany in September 1987, the year before he kicked off his Never Ending Tour.

In 1988, Dylan kicked off what's been coined his "Never Ending Tour." Rather than play the greatest hits on bloated, album-specific tours, Dylan targeted a younger generation of fans, playing smaller towns and venues. The nightly setlists changed frequently as Dylan dug deep into his vault of songs, often radically rearranging them.

Bobcats, as hard core fans are known, were hooked and soon following Dylan around the world on tour, a la Grateful Deadheads. With a relentless touring schedule averaging a hundred gigs every year since '88, to date Bob Dylan and His Band have plugged in for nearly 3,000 shows.

...And it Keeps on Truckin'

dylan 2012 — Bob Dylan performs at the Les Vieilles Charrues festival in Carhaix, France in 2012, 24 years into his Never Ending Tour.

Nobody except Dylan's accountant knows the Never Ending Tour's total box office take, and industry publications like Pollstar don't include it in their list of the highest grossing tours of all time. But Bob keeps on headin' for another joint, so far slated to play nearly forty concerts in 2019.

A Grammy Award...and a Soy Bomb

soy bomb dylan bob — Bob Dylan performs "Love Sick" as Michael "Soy Bomb" Portnoy gets carried off stage by security during the 1998 Grammy Awards at New York's Radio City Music Hall.

Dylan toured constantly in the '90s, but hadn't scored a major hit album in years. Enter 1997's "Time Out of Mind." With choice cuts like "Not Dark Yet," "Cold Irons Bound" and "Make You Feel My Love" (later covered by Adele to huge success), it was praised as Dylan's comeback and sold millions.

At the 1998 Grammy Awards, where the record won Album of the Year, Dylan nailed a performance of the swampy, bluesy number "Love Sick." Yet today it's best remembered for the infamous "Soy Bomb incident."

Mid-way through the song, a man in the audience tore off his shirt, jumped on stage next to Dylan and began busting wild, spastic dance moves. Painted across his bare chest were the words "Soy Bomb." Dylan looked puzzled, but never missed a beat. Naturally, video of the bizarre spectacle has become a YouTube classic.

"I'm in the wrong town, I should be in Hollywood"

dylan hearts of fire — Bob Dylan co-starred with Rupert Everett and Fiona in the 1987 film "Hearts of Fire."

Dylan and the silver screen are no strangers. In song lyrics, he's name-checked movie stars ranging from Bette Davis and Brigitte Bardot to Gregory Peck and Leonardo DiCaprio.

Dylan's first starring film role was as himself in the documentary "Don't Look Back," which chronicled his 1965 concert tour of England. Since, he's played an oddball cowboy in the 1973 Western, "Pat Garrett & Billy the Kid"; rocked Martin Scorsese's celebrated concert doc "The Last Waltz"; co-starred in the atrocious 1980s' flick "Hearts of Fire"; and portrayed a version of himself (alias, Jack Fate) for the esoteric, star-studded 2003 picture "Masked and Anonymous."

Has Dylan ever won an Academy Award? Yes, but not for acting. In 2001, he bagged Oscar gold for Best Original Song: "Things Have Changed" from the movie, "Wonder Boys."

Sell Out!

dylan victoria's secret ad — In 2004, Bob Dylan appeared in a TV commercial for Victoria's Secret.

While it surprises casual fans, Dylan has been selling his songs to TV commercials since 1996 when he released "The Times They Are A-Changing" for a Bank of Montreal spot. Some fans felt betrayed, especially given the song's anti-establishment gravitas.

But Dylan wasn't done making an easy sellout buck just yet. In a 1965 press conference, asked if he were going to sell out to a commercial interest, which would he choose? He joked "Ladies garments." In 2004 he made good on his word, appearing and leering in a TV commercial for Victoria's Secret.

What has followed is one commercial after another for a Forbes list of corporations: Pepsi, Cadillac, Chrysler, Apple, IBM, Kaiser-Permanente, Chobani yogurt and his latest, a 2019 Super Bowl ad for Budweiser. Nevermind that "Blowin' In The Wind" is full of resonant metaphors about a world besieged by war and hate. Bob's got bills to pay.

His Fanbase Is a Cash Cow

dylan book — Dylan's had so many books written about his career, one author jokingly titled his book "Oh No! Not Another Bob Dylan Book."

In the rock 'n' roll universe, perhaps only the Beatles and Grateful Dead enjoy fan bases as obsessed as Dylan's. Since the '60s, his music and lyrics have been so exhaustively dissected and over-analyzed by fans, it inspired their nerdy nickname, "Dylanologists."

Dylan's had so many books written about every fathomable aspect of his career, one author jokingly titled his 1991 tome "Oh No! Not Another Bob Dylan Book." Online, devotees get their daily Bob fix at Expectingrain.com, which compiles links to Dylan news and hosts a lively discussion forum.

For Dylan, this undying love has bred a pack of Bobcats ever-ready to pony-up for pricey concert tickets and $80-$100 a pop for his ongoing "Bootleg Series" CD box sets featuring vintage studio outtakes and live material.

He's Got His Own Whiskey

bob dylan's whiskey — Dylan made a big push for his whiskey, including an appearance on "The Tonight Show Starring Jimmy Fallon."

Forget celebrity spirits like George Clooney's tequila. When you need moonshine for a late-night Dylanology session to, say, connect the dots between the song "All Along The Watchtower" and the Old Testament, the perfect study companion is Dylan's "Heaven's Door" whiskey.

Introduced in 2018, the trio of American whiskeys (Tennessee bourbon, a double-barrel whiskey and a straight rye) were "curated" by Dylan and run $60 to $80 per bottle. The label art features silhouettes of Dylan's own welded-iron sculptures, which incorporate "objects found on farms and scrap yards across America."

For promotion, Dylan appeared on "The Tonight Show Starring Jimmy Fallon." Or was the bourbon-sipping Bob just a figment of Fallon's imagination? Watch the video and judge for yourself.

He's an Artist, He Don't Look Back

Dylan's endless highway — A woman examines a painting by Bob Dylan called "Endless Highway" at an exhibition at the Halcyon Gallery in London, in November 2016.

Not only has Dylan spawned 36 studio albums and sold a total of more than 100 million records worldwide, he's published eight books of his own drawings and paintings. A painter since the '60s, his works have appeared in galleries around the globe. And one of Dylan's self portraits even served as cover art for his 1970 album titled (what else?) "Self Portrait."

As a sculptor of artistic ironworks, Dylan recently collected just over $84,000 from the U.S. State Department for a 4-foot-high sculpture to be displayed at the U.S. Embassy in Mozambique. Critics ask why a rock star with an estimated net worth of $200 million couldn't donate the piece? The answer, my friend, depends on Bob's financial whim.