How Bob Dylan built a successful career. Explore key moments that defined the journey.
Bob Dylan is a highly influential American singer-songwriter, renowned as one of history's greatest songwriters. His career, spanning over six decades, has profoundly impacted popular culture. Having sold over 125 million records, Dylan stands as one of the best-selling musicians ever. In the early 1960s, he revolutionized folk music by incorporating sophisticated lyrical techniques and intellectualism, drawing from classic literature and poetry. Dylan's lyrics, infused with political, social, and philosophical themes, challenged pop music norms and resonated with the burgeoning counterculture movement.
Between 1923 and 1963, songs were written that would later feature on Bob Dylan's album Shadows in the Night, released in February 2015.
On January 31, 1959, 17-year-old Bob Dylan saw Buddy Holly perform at the Duluth Armory, four days before Holly’s fatal plane crash, which electrified him.
In September 1959, Bob Dylan enrolled at the University of Minnesota and began performing at the Ten O'Clock Scholar coffeehouse.
In January 1961, Bob Dylan traveled to New York City to perform and visit his musical idol Woody Guthrie.
From February 1961, Bob Dylan played at clubs around Greenwich Village, befriending folk singers and picking up material.
In April 1961, Joan Baez met Bob Dylan, after she had already released her first album and was acclaimed as the "Queen of Folk".
In 1961, Bob Dylan arrived in New York, marking the beginning of his rise to stardom, as depicted in the film "A Complete Unknown" released in 2024.
Material recorded in Minneapolis in 1961 was included on the 1969 release of the Great White Wonder bootleg album.
On March 19, 1962, Bob Dylan's debut album, "Bob Dylan", was released, consisting of traditional folk, blues and gospel material.
From December 1962 to January 1963, Bob Dylan made his first trip to the United Kingdom to appear in Madhouse on Castle Street.
In December 1962, "Mixed-Up Confusion", recorded during the Freewheelin' sessions, was released as Bob Dylan's first single but swiftly withdrawn.
His next album would be the first since his 1962 debut to fail to make the Top 50.
In 1962, Bob Dylan released his debut album, "Bob Dylan", featuring traditional folk songs.
In 1962, Bob Dylan taped songs for Leeds Music, one of his earliest music publishers.
In 1962, Bob Dylan wrote the song "John Brown", an unreleased song about how enthusiasm for war ends in mutilation and disillusionment.
In 1962, Lyrics: Since 1962 was published by Simon & Schuster in the fall of 2014. The book, edited by literary critics, offered variant versions of Dylan's songs, sourced from out-takes and live performances. A limited edition of 50 books, signed by Dylan, was priced at $5,000.
From December 1962 to January 1963, Bob Dylan performed in London folk clubs and learned material from UK performers.
On May 10, 1963, Bob Dylan's performance at Brandeis University was taped, which was later released in 2011 as Bob Dylan in Concert – Brandeis University 1963.
In May 1963, Bob Dylan's second album, "The Freewheelin' Bob Dylan", was released, establishing him as a singer-songwriter with protest songs like "Blowin' in the Wind".
In July 1963, Joan Baez invited Bob Dylan to join her on stage at the Newport Folk Festival, which then set the stage for similar duets over the next two years.
On August 28, 1963, Bob Dylan and Joan Baez sang together at the March on Washington, where Dylan performed "Only a Pawn in Their Game" and "When the Ship Comes In".
Between 1923 and 1963, songs were written that would later feature on Bob Dylan's album Shadows in the Night, released in February 2015.
Bob Dylan appeared at the Newport Folk Festival in 1963.
In 1963, Bob Dylan released "The Freewheelin' Bob Dylan", which included "Blowin' in the Wind", an anthem for the civil rights and antiwar movements.
On June 9, 1964, "Another Side of Bob Dylan" was recorded in a single evening, showcasing a lighter mood and signaling Dylan's move away from protest songs.
Between late 1964 and the middle of 1966, Bob Dylan created a body of work that remains unique.
Bob Dylan appeared at the Newport Folk Festival in 1964.
Bob Dylan began writing Tarantula, a freeform book of prose-poetry, in 1964.
From 1962 to 1964, Bob Dylan taped songs for Witmark Music.
In 1964, Bob Dylan released "The Times They Are a-Changin'", which became an anthem for the civil rights and antiwar movements.
In January 1965, Bob Dylan began recording material that would be released in November 2015 as part of The Bootleg Series Vol. 12: The Cutting Edge 1965–1966.
In March 1965, Bob Dylan's album "Bringing It All Back Home" was released, marking a shift in his music with the inclusion of electric instruments. The album featured the single "Subterranean Homesick Blues," accompanied by an innovative music video.
In July 1965, Bob Dylan's single "Like a Rolling Stone" reached number two on the US chart. The song later topped Rolling Stone's list of "The 500 Greatest Songs of All Time" in both 2004 and 2011.
On September 24, 1965, Bob Dylan began a six-month tour of the US and Canada with the Hawks.
In 1965, Bob Dylan adopted electrically amplified rock instrumentation and recorded "Bringing It All Back Home" and "Highway 61 Revisited", sparking controversy among folk purists. He also released the single "Like a Rolling Stone".
In 1965, Bob Dylan headlined the Newport Folk Festival and performed his first electric set since high school. The performance was met with a mixed reaction, including both cheering and booing from the audience, leading Dylan to leave the stage after only three songs.
In 1965, Bob Dylan played a Fender Stratocaster at the Newport Folk Festival, which was later sold for $965,000 in December 2013.
In 1965, Bob Dylan's controversial performance at the Newport Folk Festival occurred, a key event in his rise to stardom which is portrayed in the 2024 film "A Complete Unknown".
On February 5, 1966, Bob Dylan's 1966 concert tour commenced in White Plains, New York. Recordings from the tour were released in November 2016.
In February 1966, Bob Dylan recorded the double album "Blonde on Blonde" in Nashville, featuring session musicians and contributions from Robbie Robertson and Al Kooper.
In March 1966, Bob Dylan completed recording material that would be released in November 2015 as part of The Bootleg Series Vol. 12: The Cutting Edge 1965–1966.
In May 1966, Bob Dylan toured Europe, splitting each show into an acoustic set followed by an electric performance with the Hawks, causing controversy.
On May 17, 1966, during a concert at the Manchester Free Trade Hall in England, Bob Dylan was infamously labeled "Judas" by an audience member due to his electric performance. Dylan responded defiantly, instructing his band to "Play it fucking loud!"
Between late 1964 and the middle of 1966, Bob Dylan created a body of work that remains unique.
In 1966, Bob Dylan began to edit D. A. Pennebaker's film of his 1966 tour.
In 1966, Bob Dylan released the rock album "Blonde on Blonde".
In 1966, The Band were Bob Dylan's backing band on his tour.
In 1967, Bob Dylan and The Band recorded the Basement Tapes at their homes in Woodstock, New York, which would later be released in a comprehensive edition in November 2014.
In 1967, Bob Dylan recorded outtakes for his album John Wesley Harding, which would later be released in 2019 as part of The Bootleg Series Vol. 15.
In 1967, Bob Dylan released the album "John Wesley Harding", exploring country music and rural themes.
In 1967, Bob Dylan wrote an unreleased song that would later be used in the 2007 film "I'm Not There."
In 1967, The Band recorded The Basement Tapes with Bob Dylan.
On January 20, 1968, Bob Dylan made his first live appearance in twenty months at a memorial concert for Woody Guthrie held at Carnegie Hall, backed by the Band.
In November 1968, Bob Dylan co-wrote "I'd Have You Anytime" with George Harrison, who later recorded it along with Dylan's "If Not for You" for his album All Things Must Pass.
In 1968, Bob Dylan's visual art was first publicly seen via a painting he contributed for the cover of The Band's "Music from Big Pink" album.
In May 1969, Bob Dylan appeared on the first episode of The Johnny Cash Show, singing a duet with Cash on "Girl from the North Country" and performing "Living the Blues" and "I Threw It All Away".
In July 1969, the first "bootleg recording", Great White Wonder, appeared in West Coast shops, containing Bob Dylan material recorded in Minneapolis in 1961 and seven Basement Tapes songs.
From 1969, Bob Dylan had recording sessions for the making of the Self Portrait and New Morning albums.
In 1969, Bob Dylan recorded songs with Johnny Cash in Nashville, which would later be released in 2019 as part of The Bootleg Series Vol. 15.
In 1969, Bob Dylan released Nashville Skyline, featuring Nashville musicians, a duet with Johnny Cash, and the single "Lay Lady Lay".
In 1969, Bob Dylan released the album "Nashville Skyline", exploring country music and rural themes.
On May 1, 1970, Bob Dylan recorded a session with George Harrison, which was later released in February 2021.
In June 1970, Bob Dylan released the double LP Self Portrait, which included few original songs and was poorly received.
In October 1970, Bob Dylan released New Morning, considered a return to form after the negative reception of Self Portrait.
At the end of 1970, Bob Dylan informed Macmillan that he was ready to publish Tarantula, a book of prose-poetry he had written during a creative burst in 1964-65.
In 1970, Bob Dylan recorded songs with Earl Scruggs which would later be released in 2019 as part of The Bootleg Series Vol. 15.
In 1970, Bob Dylan released "New Morning", an album he later devoted chapters to in his memoir, Chronicles: Volume One.
In 1970, Bob Dylan released the album "New Morning", exploring country music and rural themes.
In 1970, Bob Dylan's album "Self Portrait" featured his painting of a human face on the cover, showcasing his visual art.
In 1970, Bob Dylan's management contract with Albert Grossman ended.
On August 1, 1971, Bob Dylan made a surprise appearance at George Harrison's Concert for Bangladesh, attracting media coverage due to his rare live performances.
On November 4, 1971, Bob Dylan recorded "George Jackson", a protest song about the killing of Black Panther George Jackson, and released it a week later.
Until 1971, Bob Dylan had recording sessions for the making of the Self Portrait and New Morning albums.
In 1972, Bob Dylan joined Sam Peckinpah's film Pat Garrett and Billy the Kid, providing the soundtrack and playing the character "Alias". He also protested the move to deport John Lennon and Yoko Ono.
In 1972, Michael Gray published Song & Dance Man: The Art of Bob Dylan, initiating serious critical scrutiny of Dylan's work in the context of the English literary tradition.
In 1973, Bob Dylan signed with David Geffen's Asylum Records and recorded the album Planet Waves with the Band, including two versions of "Forever Young".
In 1973, Bob Dylan's book "Writings and Drawings" was published, revealing more of his artwork to the public.
In January 1974, Bob Dylan, backed by the Band, embarked on a North American tour of 40 concerts, his first tour in seven years. A live album, Before the Flood, was released.
In September 1974, Bob Dylan recorded the album "Blood on the Tracks", filled with songs about relationships, after his tour and estrangement from his wife.
In 1974, Bob Dylan embarked on the Bob Dylan & The Band tour, recordings of which were released on September 20, 2024 as a 27-disc CD boxset called The 1974 Live Recordings.
In 1974, Bob Dylan's album "Planet Waves" featured one of his paintings on the cover.
Columbia Records released a selection of the Basement Tapes in 1975 as The Basement Tapes.
In 1975, "Blood on the Tracks" was released and initially received mixed reviews, with some critics noting its "shoddiness".
In 1975, Bob Dylan released "The Basement Tapes" and "Blood on the Tracks".
In 1975, Dylan championed Rubin "Hurricane" Carter with his ballad "Hurricane" and performed the song throughout his Rolling Thunder Revue tour.
In 1975, Dylan's Rolling Thunder Revue tour served as the backdrop for his film "Renaldo and Clara", a mix of narrative, concert footage, and reminiscences.
In 1975, Joan Baez toured with Bob Dylan as a performer on his Rolling Thunder Revue.
In 1975, the album The Basement Tapes was released, containing just 24 tracks from the material which Dylan and the Band had recorded at their homes in Woodstock, New York in 1967.
In the fall of 1975, Bob Dylan embarked on the Rolling Thunder Revue tour. Documentary footage filmed during the tour was used in the 2019 film Rolling Thunder Revue: A Bob Dylan Story.
In January 1976, Dylan released the album Desire, which featured songs with a travelogue-like narrative style influenced by Jacques Levy.
In November 1976, Bob Dylan appeared at The Band's farewell concert alongside Eric Clapton, Muddy Waters, Van Morrison, Neil Young, and Joni Mitchell.
In 1976, Bob Dylan's album Desire reached number one on the charts.
In April and May 1978, Dylan recorded the album "Street-Legal" at Rundown Studios in Santa Monica, California.
In September 1978, Dylan brought his year-long world tour to the US, drawing press descriptions of a "Las Vegas Tour" due to its look and sound.
In 1978, Bob Dylan held his tour of Tokyo concerts from February 28 and March 1, the full recordings of which were released on November 17, 2023 as The Complete Budokan 1978.
In 1978, Dylan's film "Renaldo and Clara" was released and received negative reviews, later followed by a more widely released two-hour edit with more concert performances.
In 1978, Joan Baez starred as "The Woman In White" in the film Renaldo and Clara, which was directed by Bob Dylan.
In 1979, Bob Dylan started his 'Born Again' Christian period, which was described by Rolling Stone as "an intense, wildly controversial time that produced three albums and some of the most confrontational concerts of his long career".
In 1979, Dylan released "Slow Train Coming" and later won the Grammy Award for Best Male Rock Vocal Performance for "Gotta Serve Somebody".
In 1980, Bob Dylan began a period which included rehearsals, live recordings, out-takes and alternative takes from Shot of Love. This period was later revisited in the 2021 Bootleg Series Vol. 16.
In late 1979 and early 1980, during his tour, Dylan refused to play his older, secular works, and delivered declarations of his Christian faith from the stage.
In late 1980, Dylan briefly played concerts billed as "A Musical Retrospective", and released his second Christian album, "Saved", which received mixed reviews.
In 1981, Bob Dylan's 'Born Again' Christian period ended, a period described by Rolling Stone as "an intense, wildly controversial time that produced three albums and some of the most confrontational concerts of his long career".
In 1981, Dylan released "Shot of Love", featuring his first secular compositions in more than two years, mixed with Christian songs.
In 1983, Dylan recorded the album "Infidels" with Mark Knopfler as lead guitarist and producer, resulting in several unreleased songs.
In 1984, Bob Dylan and Joan Baez toured together again with Carlos Santana.
On July 13, 1985, Dylan performed at the Live Aid concert in Philadelphia and made controversial remarks about using funds to pay farmers' mortgages.
In October 1985, Dylan released the box set "Biograph", featuring 53 tracks, including 18 previously unreleased songs.
In 1985, Bob Dylan completed a period which included rehearsals, live recordings, out-takes and alternative takes from Infidels and Empire Burlesque. This period was later revisited in the 2021 Bootleg Series Vol. 16.
In April 1986, Dylan collaborated with Kurtis Blow, adding vocals to "Street Rock" on his album Kingdom Blow, marking a foray into rap.
In 1986, Bob Dylan toured with Tom Petty and the Heartbreakers, sharing vocals on several songs each night.
In 1987, Dylan toured with The Grateful Dead, and he starred in the movie "Hearts of Fire", which was a critical and commercial flop.
On June 7, 1988, Dylan initiated the Never Ending Tour, performing with a back-up band featuring guitarist G. E. Smith, a tour that would continue for the next 30 years.
In 1989, Bob Dylan released "Oh Mercy", an album he later devoted chapters to in his memoir, Chronicles: Volume One.
In May 1990, the remaining members of the Traveling Wilburys recorded a second album, Traveling Wilburys Vol. 3.
In 1990, Dylan released "Under the Red Sky", which received negative reviews and sold poorly.
In February 1991, Bob Dylan received a Grammy Lifetime Achievement Award from Jack Nicholson. The event coincided with the start of the Gulf War, and Dylan played "Masters of War". He also gave a short speech paraphrasing Rabbi Samson Raphael Hirsch.
In 1991, the unreleased songs "Blind Willie McTell", "Foot of Pride", and "Lord Protect My Child" from the "Infidels" sessions were released on "The Bootleg Series Volumes 1–3 (Rare & Unreleased) 1961–1991".
On October 16, 1992, the thirtieth anniversary of Bob Dylan's debut album was celebrated with a concert at Madison Square Garden, named "Bobfest" by Neil Young. The event featured performances by John Mellencamp, Stevie Wonder, Lou Reed, Eddie Vedder, Dylan, and others.
In 1992, Bob Dylan released "Good as I Been to You", an album covering traditional folk and blues songs, marking a return to his roots.
In 1993, Bob Dylan released "World Gone Wrong", another album featuring traditional folk and blues songs, continuing his return to his musical roots.
In August 1994, Bob Dylan played at Woodstock '94, where Rolling Stone called his performance "triumphant".
In 1994, Random House published "Drawn Blank", a book of Bob Dylan's drawings.
Since 1994, Bob Dylan has published nine books of paintings and drawings, and his work has been exhibited in major art galleries.
Since 1994, Bob Dylan has published nine books of paintings and drawings, showcasing his visual art.
In 1996, Bob Dylan began recording the Time Out of Mind Sessions, which would later be released in January 2023 as The Bootleg Series Vol. 17.
In January 1997, Bob Dylan booked recording time with Daniel Lanois at Miami's Criteria Studios for a new album.
In 1997, Bob Dylan completed recording the Time Out of Mind Sessions, which would later be released in January 2023 as The Bootleg Series Vol. 17.
In 1997, Bob Dylan released "Time Out of Mind", which earned him the Grammy Award for Album of the Year.
In 1998, Stanford University sponsored the first international academic conference on Bob Dylan held in the United States.
In 1998, The Bootleg Series Vol. 4: Bob Dylan Live 1966, a recording of the Manchester Free Trade Hall concert, was released.
In 1999, a remastered CD release of the album "Street-Legal" restored some of the songs' strengths by improving the sound and mixing.
In 2000, "Most of the Time", was prominently featured in the film High Fidelity.
On September 11, 2001, Bob Dylan released the album "Love and Theft", which he produced under the alias Jack Frost.
In 2003, Bob Dylan revisited his evangelical songs for the project Gotta Serve Somebody: The Gospel Songs of Bob Dylan. Also in 2003, Dylan released the film Masked & Anonymous, which he co-wrote and starred in.
In December 2004, Bob Dylan's memoir, Chronicles: Volume One, reached number two on The New York Times' Hardcover Non-Fiction bestseller list.
In 2004, Bob Dylan appeared in a TV advertisement for Victoria's Secret.
In 2004, Richard F. Thomas at Harvard University created a freshman seminar titled "Dylan", exploring his connections with classical poets.
In 2005, Martin Scorsese's Bob Dylan documentary, No Direction Home, was broadcast on BBC Two in the UK and on PBS in the US.
On May 3, 2006, Bob Dylan's career as a radio presenter began with his weekly program, Theme Time Radio Hour, on XM Satellite Radio.
In August 2006, Bob Dylan released the album Modern Times, which entered the US charts at number one.
On October 1, 2007, Columbia Records released the triple CD retrospective Dylan, anthologizing Bob Dylan's entire career under the Dylan 07 logo.
In October 2007, Bob Dylan participated in a multi-media campaign for the 2008 Cadillac Escalade.
In 2007, Todd Haynes released "I'm Not There", a film inspired by Bob Dylan's music and life, featuring six actors portraying different facets of Dylan. The film included Dylan's unreleased 1967 song from which it takes its name.
In 2007, the first public exhibition of Bob Dylan's paintings, "The Drawn Blank Series," opened at the Kunstsammlungen in Chemnitz, Germany, showcasing over 200 watercolors and gouaches made from original drawings.
In October 2008, The Bootleg Series Vol. 8 – Tell Tale Signs was released, containing live performances and outtakes from selected studio albums.
In 2008, Bob Dylan participated in a multi-media campaign for the 2008 Cadillac Escalade.
In April 2009, Bob Dylan broadcast the 100th episode of his radio series, Theme Time Radio Hour, with the theme "Goodbye".
On April 28, 2009, Bob Dylan released the album Together Through Life, which originated from a song for a French movie.
In 2009, Bob Dylan appeared with rapper will.i.am in a Pepsi ad that debuted during Super Bowl XLIII, marking the highest profile endorsement of his career to date.
From September 2010 until April 2011, the National Gallery of Denmark exhibited 40 large-scale acrylic paintings by Bob Dylan, titled "The Brazil Series".
On October 18, 2010, Volume 9 of Dylan's Bootleg Series, The Witmark Demos, was issued, comprising 47 demo recordings of songs taped between 1962 and 1964.
On April 12, 2011, Legacy Recordings released Bob Dylan in Concert – Brandeis University 1963, taped at Brandeis University on May 10, 1963.
In April 2011, the National Gallery of Denmark concluded its exhibition of Bob Dylan's "The Brazil Series", which had begun in September 2010 and featured 40 large-scale acrylic paintings.
In July 2011, the Gagosian Gallery, a leading contemporary art gallery, announced their representation of Bob Dylan's paintings, marking a significant step in his visual arts career.
On September 11, 2012, Bob Dylan's 35th studio album, Tempest, was released.
In November 2012, Bob Dylan's second show at the Gagosian Gallery, "Revisionist Art", opened. The show featured thirty paintings transforming and satirizing popular magazines.
Since 2012, Bob Dylan had not released a full album of original material until Rough and Rowdy Ways was released on June 19.
In February 2013, Bob Dylan exhibited the "New Orleans Series" of paintings at the Palazzo Reale in Milan.
In August 2013, Britain's National Portrait Gallery in London hosted Bob Dylan's first major UK exhibition, "Face Value", featuring twelve pastel portraits.
In August 2013, Volume 10 of Dylan's Bootleg Series, Another Self Portrait (1969–1971), was released, containing previously unreleased tracks.
In November 2013, Columbia Records released a boxed set containing all 35 Dylan studio albums as Bob Dylan: Complete Album Collection: Vol. One.
In November 2013, the Halcyon Gallery in London mounted "Mood Swings", an exhibition in which Bob Dylan displayed seven wrought iron gates he had made.
In December 2013, the Fender Stratocaster that Bob Dylan played at the 1965 Newport Folk Festival was sold for $965,000, becoming the second highest price paid for a guitar at auction.
In June 2014, Bob Dylan's hand-written lyrics of "Like a Rolling Stone" were sold at auction for $2 million, setting a record for a popular music manuscript.
In November 2014, a comprehensive edition of the Basement Tapes, recorded by Bob Dylan and the Band in 1967, was released as The Bootleg Series Vol. 11: The Basement Tapes Complete. The album included 138 tracks in a six-CD box and won the Grammy Award for Best Historical Album. The box set earned a score of 99 on Metacritic.
In February 2015, Bob Dylan accepted the MusiCares Person of the Year award for his philanthropic and artistic contributions.
In February 2015, Bob Dylan released Shadows in the Night, featuring ten songs written between 1923 and 1963, described as part of the Great American Songbook. The album debuted at number one in the UK Albums Chart in its first week of release.
In November 2015, The Bootleg Series Vol. 12: The Cutting Edge 1965–1966 was released, consisting of previously unreleased material from the three albums Dylan recorded between January 1965 and March 1966. The Best of the Cutting Edge entered the Billboard Top Rock Albums chart at number one on November 18, based on its first-week sales.
In November 2016, The 1966 Live Recordings was released, including every known recording of Bob Dylan's 1966 concert tour.
In November 2016, the Halcyon Gallery featured a collection of drawings, watercolors and acrylic works by Bob Dylan, known as "The Beaten Path", depicting American landscapes inspired by his travels.
In 2016, Bob Dylan was awarded the Nobel Prize in Literature "for having created new poetic expressions within the great American song tradition".
In March 2017, Bob Dylan released a triple album of 30 more recordings of classic American songs, Triplicate. Dylan's 38th studio album was recorded in Hollywood's Capitol Studios and features his touring band.
On June 5, 2017, Bob Dylan's Nobel Lecture was posted on the Nobel Prize website.
In 2017, the musical "Girl from the North Country", written and directed by Conor McPherson and featuring Bob Dylan's songs, premiered in London. The musical tells the stories of various characters during the Depression years in Duluth, Minnesota, Dylan's birthplace.
In April 2018, Bob Dylan made a contribution to the compilation EP Universal Love, a collection of reimagined wedding songs for the LGBT community. Dylan recorded the 1929 song "He's Funny That Way", changing the gender pronoun from "She's Funny That Way".
In April 2018, The New York Times reported that Bob Dylan was launching Heaven's Door, a range of three whiskeys. Dylan has been involved in both the creation and the marketing of the range.
In October 2018, the Halcyon Gallery mounted an exhibition of Bob Dylan's drawings, "Mondo Scripto". These works consisted of his hand-written lyrics illustrated by drawings.
On November 2, 2018, Bob Dylan released More Blood, More Tracks as Volume 14 in the Bootleg Series. The set comprises all Dylan's recordings for Blood On the Tracks and was issued as a single CD and also as a six-CD Deluxe Edition.
By April 2019, Bob Dylan and his band had performed over 3,000 shows as part of the Never Ending Tour, supported by long-time bassist Tony Garnier.
In 2019, "Retrospectrum," the largest retrospective of Bob Dylan's visual art to date, debuted at the Modern Art Museum in Shanghai, consisting of over 250 works in a variety of media.
In 2019, Netflix released Rolling Thunder Revue: A Bob Dylan Story by Martin Scorsese, billed as "Part documentary, part concert film, part fever dream". Coinciding with the film release, the box set The Rolling Thunder Revue: The 1975 Live Recordings, was released by Columbia Records.
On March 26, 2020, Bob Dylan released "Murder Most Foul", a seventeen-minute song revolving around the Kennedy assassination, on his YouTube channel.
On April 17, 2020, Bob Dylan released another new song, "I Contain Multitudes".
On September 21, 2020, Bob Dylan resurrected Theme Time Radio Hour with a two-hour special with the theme of "Whiskey".
In December 2020, Bob Dylan sold his entire song catalog to Universal Music Publishing Group for an estimated price of more than $300 million.
In 2020 Bob Dylan released the album 'Rough and Rowdy Ways' and subsequently performed nine of the ten songs on the album as part of the 'Rough and Rowdy Ways World Wide Tour, 2021-2024'.
In February 2021, Columbia Records released 1970, a three-CD set of recordings from the Self Portrait and New Morning sessions.
In July 2021, livestream platform Veeps presented a 50-minute performance by Bob Dylan, Shadow Kingdom: The Early Songs of Bob Dylan. Filmed in black and white with a film noir look, Dylan performed 13 songs in a club setting with an audience.
In September 2021, Bob Dylan's touring company announced the 'Rough and Rowdy Ways World Wide Tour, 2021-2024', which replaced Dylan's varied set lists with a more stable repertory.
On November 30, 2021, a version of "Retrospectrum," an art exhibition including a new series of paintings called "Deep Focus," opened at the Frost Art Museum in Miami.
In 2021, Bob Dylan recorded "Blowin' in the Wind", which was later auctioned on July 7, 2022 for GBP £1,482,000.
On July 7, 2022, Christie's, London, auctioned a 2021 recording of Bob Dylan singing "Blowin' in the Wind" for GBP £1,482,000.
On November 1, 2022, Bob Dylan's third full-length book, "The Philosophy of Modern Song", containing 66 essays on songs by other artists, was published.
In January 2023, Bob Dylan released The Bootleg Series Vol. 17: Fragments – Time Out of Mind Sessions (1996–1997) in multiple formats.
In June 2023, the soundtrack to the 2021 film Shadow Kingdom was released on 2 LP and CD formats.
On November 17, 2023, Bob Dylan released The Complete Budokan 1978, containing the full recordings of the February 28 and March 1 Tokyo concerts from his 1978 Tour.
On August 30, 2024, the soundtrack of the biographical film Reagan was released, featuring Bob Dylan's cover version of Cole Porter's song "Don't Fence Me In".
On September 20, 2024, Bob Dylan released The 1974 Live Recordings, a 27-disc CD boxset of recordings from the 1974 Bob Dylan & The Band tour, featuring 417 previously unreleased live tracks.
On December 25, 2024, the film "A Complete Unknown", portraying Bob Dylan's rise to stardom from 1961 to 1965, opened in the U.S. The film received favorable reviews, especially for Timothée Chalamet's portrayal of Dylan.
In 2024, the Rough and Rowdy Ways World Wide Tour continued, replacing Dylan's varied set lists with a more stable repertory, performing nine of the ten songs on his 2020 album.
In February 2025, Bob Dylan announced a U.S. leg of his Rough and Rowdy Ways World Wide Tour, commencing in Tulsa, Oklahoma on March 25, and ending in Williamsport, Pennsylvania on April 22. It was also announced that Dylan would take part in the Outlaw Music Festival 2025 Tour, appearing alongside Willie Nelson and other artists, beginning on May 13 in Phoenix, Arizona, and finishing on September 19 in Troy, Wisconsin.