- Although he had several stalkers over the years, perhaps the most dogged was the self-titled Dylanologist, A.J. Weberman. This obsessed fan started the "Dylan Liberation Front," protesting that Dylan had sold out and has abandoned his political causes (in reality, Dylan was never very political). Weberman staged several "protests" in front of Dylan's home, rooted through Dylan's garbage repeatedly, and accused Dylan of heroin use. After Weberman pushed aside Dylan's wife, Sara, and broke into Dylan's home, Dylan lost his patience and defeated his considerably beefier stalker in a fight.
- Despite rumors that he hates rap music, Dylan cites several rappers as having "brilliant minds" and, in his "Chronicles" states that he is a big fan of several Old School rappers, particularly Public Enemy, who were one of his favorite artists of that era. Many see an early connection to rap in Dylan's music, particularly the song "Subterranean Homesick Blues". However, Dylan apparently dislikes the commercialism of much modern hip-hop and warned popular rappers that "sometimes less is more". When he hosted "Bob Dylan's Radio Theme Time Hour", during his "Mother's Day" hour in 2008, Dylan played "Momma Said Knock You Out" by LL Cool J and was heard to rap along with the first verse. LL Cool J himself was thrilled when he heard this.
- Dylan once visited artist and filmmaker Andy Warhol when he came to pick up actress/model Edie Sedgwick, whom he was dating at the time, and found himself the subject of Warhol's movie camera. Dylan responded by picking up an original Warhol painting and taking it with him "for payment" for being filmed, which he used first as a dartboard, then traded for a sofa (he apologized to Warhol in a press interview years later for his attitude).
- For the recording of the famous, rambling song "Rainy Day Women # 12 & 35" (with its chorus of "everybody must get stoned!"), Dylan took the group of mostly straight-laced, professional session musicians he was recording with, got them very drunk and had them smoke pot. When they returned, he had each man play a different instrument to what they usually played. After this went on, somebody asked Dylan when they were actually going to record the song, Dylan countered, "That was it."
- 1964: Introduced The Beatles to pot-smoking, during their first meeting in New York; each told the press later, "We just laughed all night.".
- He has developed the habit in recent years of making impromptu visits to the childhood homes of musical colleagues he admires. He told Rolling Stone magazine that he has visited the childhood homes of Neil Young, John Lennon and Bruce Springsteen. In Springsteen's case, some neighbors called police when they allegedly saw Dylan peering into the window of Springsteen's childhood home in Long Branch, New Jersey, He was questioned by a pair of police officers who didn't recognize him. He was not arrested.
- At the famous "Johnny Cash at San Quentin" concert, Johnny Cash introduced a song co-written by Dylan, describing him as "...the greatest writer of our time".
- Awarded a 2008 Pulitzer Prize (Special Citation "for his profound impact on popular music and American culture, marked by lyrical compositions of extraordinary poetic power"). He is the first rock or folk musical artist to win this prestigious honor.
- Always something of a Casanova, he had his first steady girlfriend at 14 and was seeing as many as five girls at once by the time he was in college.
- He turned down an offer to headline the legendary Woodstock Festival in 1969 (Jimi Hendrix ultimately headlined), even though he had been living on a farm in Woodstock for many years at that point.
- Widely regarded as one of the greatest songwriters in the history of popular music, he holds the impressive distinction of having had his songs covered by nearly 3,000 artists. Some notable covers of his songs: "Quinn the Eskimo" - Manfred Mann; "Mr. Tambourine Man" - The Byrds; "All Along the Watchtower" - Jimi Hendrix; "It Ain't Me, Babe" - Johnny Cash, The Turtles; "Knockin' on Heaven's Door" - Eric Clapton; as well as Guns N' Roses, "Maggie's Farm" - Rage Against the Machine, "Desolation Row" - My Chemical Romance, and there are over 100 covers of "Blowin' in the Wind". Other well known artists to cover Dylan songs include U2, Dave Matthews Band, Sheryl Crow, Stevie Wonder, Joe Cocker, Diana Ross, Rod Stewart, Elvis Costello, Phil Collins, Bryan Ferry, Steve Hackett, Steve Howe, Emerson Lake and Palmer, The Beach Boys and Adele.
- His favorite movie is Shoot the Piano Player (1960) by François Truffaut.
- His song "Like a Rolling Stone" was named # 1 on Rolling Stone's 500 Greatest Songs of All Time (2004). Other songs listed include: "Blowin' in the Wind" (# 14), "The Times Are A-Changin'" (# 59), "Tangled Up In Blue" (# 68), "Mr. Tambourine Man" (# 106), "Desolation Row" (# 185), "Knocking on Heaven's Door" (# 190), "Positively 4th Street" (# 203), "Just Like a Woman" # (230), "Subterranean Homesick Blues" (# 332), "Highway 61 Revisited" (# 364), and "Visions of Johanna" (# 403).
- He no longer plays the guitar when performing live, instead either playing on the keyboards or only on his harmonica. Although this has erroneously claimed to be due to back problems, it is apparently due to his opinion of the band's sound. He has accumulated several talented guitarist in his long-time touring band who fill the void.
- Dylan's father owned a furniture store when young "Bobby" was in high school, and sent him once on rounds, to collect from installment-plan customers late on their bills. When Dylan returned and told his father "Dad, those people don't have any money," his father replied "Some of those people make as much money as I do; they just don't know how to manage it." The lesson stuck with Dylan.
- Between the ages of 10 and 18, Dylan ran away from home seven times.
- 5/27/97: Admitted to hospital for treatment of a "potentially life-threatening infection".
- He has nine grandchildren - four from his step-daughter, Maria, one each from Jesse and Samuel, and three from Jakob Dylan. He also has a "World's Greatest Grandpa" bumper sticker that he proudly displays on his car.
- Said that when he performs "All Along the Watchtower," he thinks of it as a tribute to Jimi Hendrix. Although Dylan was the song's original writer, Hendrix's cover is the best known version of the song.
- February 1964: Dylan and three friends drove south from New York to see some of the US heartland. He insisted they stop unannounced to see poet Carl Sandburg in North Carolina. To his lasting disappointment, Dylan left after some ten minutes when he sadly realized he couldn't get the venerable man of letters to take him seriously as a fellow poet.
- Fan of Elvis Presley.
- Hitchhiked from Minnesota to New York after leaving college, paying his way by doing odd jobs and sleeping wherever he could find space. Stopped at a courthouse along the way and legally changed his name from Zimmerman to Dylan (when asked later if his name was spelled like Dylan Thomas, he answered "No, like Bob Dylan").
- Attended the University of Minnesota briefly after graduating high school; flunked out by non-participation ("refusin' to see a rabbit die" in a science class, and reading Kant instead of a required textbook), and cutting classes to frequent the local Dinkytown coffeehouses.
- According to the stage manager at Hibbing High School, and a local documentary, the piano that he played on stage is currently the same one that the school uses during their drama performances.
- Some of his biggest influences are Hank Williams, Muddy Waters, Ferdinand 'Jelly Roll' Morton, Leadbelly, Mance Lipscomb, Big Joe Williams and Woody Guthrie.
- Rode a 500cc T100S/R Triumph Tiger motorcycle upon which he famously crashed
- "All Along the Watchtower" is the song he's performed the most, with nearly 2,000 known performances. It is also, including Jimi Hendrix's performance of the song, the song that's been most frequently featured on film and TV soundtracks.
- He is a big fan of the films of John Ford.
- Borrowed lines from a Japanese book "Confessions of a Yakuza" for lyrics in the songs of his album "Love and Theft" - the author was apparently flattered by this.
- He refused the use of his recording of the song "Moonshiner" in the soundtrack for the film An American Werewolf in London (1981) due to his objections to the moral content of the script since he was at the height of his Christian born-again phase at that point. Ironically, several Dylan songs were used nearly 30 years later in the TV show True Blood (2008), which has similar content.
- Appears on sleeve of The Beatles' "Sgt Pepper's Lonely Hearts Club Band".
- Early 1980s: Visited Israel on what was supposed to be a private trip; this was spoiled when he was photographed at Jerusalem's Wailing Wall, and the picture made headlines around the world.
- Historically, he rarely fraternized or even spoke extensively with the studio band members he recorded with. The musicians would usually await instruction only from the producer at the time and were frequently rankled by Dylan's chilly behavior and lack of credit they received after recording. Recently, when Dylan has begun producing his own albums and recording with the touring band he assembled in the '80s and '90s, this has been said to have changed somewhat.
- When he won the 2016 Nobel Prize in Literature, he joined playwright George Bernard Shaw as the only persons to win a Nobel Prize and an Academy Award.
- By the time he was ten, Bob began to get piano lessons and he was beginning to listen to the country, blues, and (a little later) the rock 'n' roll played on radio late at night in Hibbing. In his teens, Bob's father bought him an electric guitar and he started a series of rock 'n' roll cover bands with friends from school and summer camp called The Jokers, The Shadow Blasters, and, lastly, The Golden Chords. Once in college, he became so excited by the folk music of Woody Guthrie that he traded his electric guitar for an acoustic one.
- At the The 40th Annual Grammy Awards (1998) he won a Grammy for best male rock singer (on "Cold Irons Bound"), best contemporary folk singer and album of the year ("Time Out of Mind").
- Was a member of The Traveling Wilburys with Beatle George Harrison, Tom Petty, Roy Orbison, and Jeff Lynne of Electric Light Orchestra.
- A father of six children. His children are: Maria Lowndes Dylan (born 21 October 1961; married to Peter Himmelman and a mother of four), Jesse Byron Dylan (born 6 January 1966; married to Susan Traylor and father of William), Anna Leigh Dylan (born 11 July 1967; she is married, but has no children), Samuel Abraham Dylan (born 30 July 1968; married to Stacy Hochheiser and father of Jonah), Jakob Luke Dylan (born 9 December 1969; married to Paige and a father of three), Desiree Gabrielle Dennis-Dylan (born 31 January 1985). His eldest child, Maria, became his step-daughter when he married Sara Lowndes, and he later adopted her as his own. His youngest daughter, Desiree, was born to his second wife, Carolyn Dennis. His other four children were all with his first wife, Sara.
- In his book, "Chronicles," Dylan indicates that the reason he began starting writing songs were the works of folk-legend Woody Guthrie (he was obsessed with Guthrie's "hopped-up union meeting sermons"), mysterious blues great Robert Johnson (saying he evoked the "dark night of the soul") and certain songs by Bertolt Brecht and Kurt Weill (due to their "tough language" and their "resilience and outrageous power").
- 1959: Played piano for Bobby Vee in a make-up band booked for show left vacant by the airplane-crash death of Buddy Holly, Ritchie Valens and The Big Bopper (aka J.P. Richardson).
- His Album "Modern Times" (2006) was voted the 8th Best Album of the Decade by Rolling Stone Magazine.
- Father of the singer/songwriter Jakob Dylan of The Wallflowers.
- 1985: Daughter Desiree Gabrielle Dennis-Dylan born. Mother is gospel-rock vocalist Carol Dennis, a backup singer who formerly worked with him and who he secretly married.
- Despite his reputation as a "protest singer", he was never very active politically and very rarely rallied for causes. Although he did some work in support of the civil right movements and often fought individual injustices (most famously, that of Rubin 'Hurricane' Carter), many of his peers in the folk community found his apparent indifference to politics frustrating.
- Some notable covers of his songs: "Quinn the Eskimo" - Manfred Mann; "Mr. Tambourine Man" - The Byrds; "All Along the Watchtower" - Jimi Hendrix; "It Ain't Me, Babe" - Johnny Cash, The Turtles; "Knockin' on Heaven's Door" - Eric Clapton; as well as Guns N' Roses, "Maggie's Farm" - Rage Against the Machine, "Desolation Row" - My Chemical Romance, and there are over 100 covers of "Blowin' in the Wind".
- Son of Abraham Zimmerman and Beatrice Stone (Beatty Zimmerman).
- He was voted the second Greatest Rock 'n' Roll Artist of all time by Rolling Stone.
- Although he avoids discussing religion now, Dylan said in a 1997 interview with Rolling Stone that he's no longer a follower of any organized religion.
- In 2012 Dylan claimed to Rolling Stone magazine that he was a philosophical believer in transfiguration. He says he came to believe in it after reading "Hell's Angel" by Sonny Barger, former president of the notorious Hell's Angels motorcycle gang, which included a passage about Bobby Zimmerman, a Hell's Angel "president" who is erroneously reported to have died in a biking accident in 1965, coincidentally the same year Dylan was at the zenith of his fame (actually it was 1961 that the biker Zimmerman died, around the time that Dylan started getting noticed in Greenwich Village). Coincidentally, Dylan's birth name was also Robert Zimmerman, a last name also shared by the book's co-authors, Kent Zimmerman and Keith Zimmerman.
- 1/18/88: Inducted into the Rock and Roll Hall of Fame by Bruce Springsteen at the Waldorf Astoria Hotel, New York City.
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