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- Bob Dylan performed at the Gaslight Cafe in New York City.
- Bob Dylan made his first appearance at New York City's Gaslight Cafe.
- Robert Allen Zimmerman legally changed his name to Robert Dylan. The legal change took place at the St. Louis County Court in Hibbing, Minnesota, and he listed his father, Abraham Zimmerman, as a witness. The new name later became his well-known stage name, Bob Dylan.
- Bob Dylan began the first recording sessions at Studio A of Columbia Recording Studios in New York with producer Tom Wilson for his third album, “The Times They Are a-Changin'.” It was his first album made up entirely of original songs. Upon its release the following February, the album reached No. 20 in the U.S. and No. 4 in the UK.
- Bob Dylan released the album "Another Side of Bob Dylan" on Columbia Records.
- Bob Dylan released the album “Highway 61 Revisited”, which marked his definitive transition to an electric sound. The album included, among others, “Like a Rolling Stone”, which reached No. 2, and the more than eleven-minute song “Desolation Row”.
- Bob Dylan's “Like a Rolling Stone” moved from number six to number two.
- Bob Dylan renewed his recording contract with Columbia Records.
- On August 2, 1969, Bob Dylan returned to his hometown of Hibbing, Minnesota, for his ten-year high school reunion, marking the class of 1959. He and his wife Sara met classmates beforehand at the local Moose Lodge, but after a confrontation with a drunken former classmate, Dylan left and ultimately did not attend the reunion itself.
- It was reported that Bob Dylan’s bootleg album Great White Wonder had sold more than 350,000 copies worldwide.
- Bob Dylan appeared at Memorial Auditorium in Buffalo, New York.
- Bob Dylan performed at The Olympia in Detroit, Michigan.
- Bob Dylan released his 19th studio album, “Slow Train Coming”, through Columbia Records, his first album following his conversion to Christianity. The religiously focused songs expressed his personal faith and emphasized the importance of Christian teaching and philosophy. The album reached No. 1 in Australia, New Zealand and Norway, No. 2 in the UK and No. 3 in the U.S. It included “Gotta Serve Somebody”, which reached No. 24 on the U.S. chart and became Dylan's last single to reach the U.S. Top 40. In 1980, it won a Grammy for Best Rock Vocal Performance, Male. According to one of the sources, the album alienated some of his longtime fans.
- “Gotta Serve Somebody” entered the U.S. chart and became Bob Dylan's twelfth U.S. Top 40 hit. The song was recorded at Muscle Shoals Sound Studios and won a Grammy for Best Rock Vocal Performance, Male, in 1980.
- The song “Gotta Serve Somebody” gave Bob Dylan his twelfth U.S. Top 40 hit. It was recorded at Muscle Shoals Sound Studios in Alabama and won the 1980 Grammy Award for Best Rock Vocal Performance, Male.
- Columbia Records released his 21st studio album, “Shot of Love,” which reached No. 6 in the UK and No. 33 in the US; its religious themes drew mixed critical reactions.
- Bob Dylan performed before more than 4,000 cadets at the US Military Academy at West Point, New York, in Eisenhower Hall. Many future army officers stood up and sang along to his anti-war song "Blowin' in the Wind".
- The album „The 30th Anniversary Concert Celebration“, honoring Bob Dylan's career, was released.
- After turning down an invitation to the original festival in 1969, he performed on the final day of Woodstock '94. On the main North Stage, he sang “It Ain't Me Babe”, “It's All Over Now, Baby Blue”, “Masters Of War”, “Just Like A Woman” and “Highway 61 Revisited”. Meanwhile, on the South Stage, Green Day frontman Billie Joe Armstrong threw handfuls of mud at fans, triggering a massive mud fight. Bassist Mike Dirnt lost his front teeth in the chaos after being struck by a security guard.
- Bob Dylan performed in Columbus, Ohio, at the Ohio State Fair.
- After a 37-year absence, Bob Dylan returned to the Newport Folk Festival, performing a two-hour, 19-song set.
- Bob Dylan's song “Like a Rolling Stone” won an Uncut magazine poll of the music, films, television shows and books that changed the world.
- The Bob Dylan biographical film I'm Not There: Suppositions on a Film Concerning Dylan premiered at the Venice Film Festival in Italy. Directed by Todd Haynes, the film features six actors portraying different aspects or periods of Dylan's life and music, including Cate Blanchett, Richard Gere, Heath Ledger and Christian Bale. Before its wider release later in 2007, the title was shortened to I'm Not There.
- During his weekly radio programme on 6 Music, Bob Dylan revealed that he was in talks with several car companies about possibly becoming the voice of their satellite navigation systems.
- Bob Dylan announced his intention to fight ticket scalpers by allowing fans to purchase only one ticket at the entrance to each concert.
- Paintings by Bob Dylan displayed at a museum in Copenhagen came under criticism from some Danish critics and academics.
- Bob Dylan was awarded the Nobel Prize in Literature, becoming the first songwriter to receive the honor. The Swedish Academy recognized him for creating new poetic expressions within the great American song tradition.