Baez first met Dylan in 1961 at Gerde's Folk City in New York City's Greenwich Village. At the time, Baez had already released her début album and her popularity as the emerging "Queen of Folk" was on the rise. Baez was initially unimpressed with the "urban hillbilly," but was impressed with one of Dylan's first compositions, "Song to Woody," and remarked that she would like to record it (although she never did).

At the start, Dylan was more interested in Baez's younger sister, Mimi, but under the glare of media scrutiny that began to surround Baez and Dylan, their relationship began to develop into something more.

By 1963, Baez had already released three albums, two of which had been certified "gold," and she invited Dylan on stage to perform alongside her at the Newport Folk Festival. The two performed the Dylan composition "With God on Our Side," a performance that set the stage for many more duets like it in the months and years to come. Typically while on tour, Baez would invite Dylan to sing on stage partly by himself and partly with her, much to the chagrin of her fans.

Before meeting Dylan, Baez's topical songs were few and far between: "Last Night I Had the Strangest Dream," "We Shall Overcome," and an assortment of negro spirituals. Baez would later say that Dylan's songs seemed to update the topics of protest and justice.

By the time of Dylan's 1965 tour of the U.K., their relationship had slowly begun to fizzle out after they had been romantically involved off and on for nearly two years. The tour and simultaneous disintegration of their relationship was documented in D.A. Pennebaker's documentary film Dont Look Back (1967).

Baez toured with Dylan as a performer on his Rolling Thunder Revue in 1975-76. She sang four songs with Dylan on the live album of the tour, The Bootleg Series Vol. 5: Bob Dylan Live 1975, The Rolling Thunder Revue, released in 2002. Baez appeared with Dylan in the one hour TV special, Hard Rain, filmed at Fort Collins, Colorado, in May 1976. Baez also starred as the 'The Woman In White' in the film Renaldo and Clara (1978), directed by Bob Dylan and filmed during the Rolling Thunder Revue.

Dylan and Baez (plus Carlos Santana) toured together again in 1984.

Baez discussed her relationship with Dylan in Martin Scorsese's documentary film No Direction Home (2005), and in the PBS American Masters biography of Baez, How Sweet the Sound (2009).

Baez penned at least two songs about Dylan. In "To Bobby", written in 1972, she urged Dylan to return to political activism, while in "Diamonds & Rust," the title track from her 1975 album, she revisited her feelings for him in warm, yet direct terms.^<32>

References to Baez in Dylan's songs are far less clear. Baez herself has suggested that she was the subject of both "Visions of Johanna" and "Mama, You Been on My Mind," although the latter was more likely about his relationship with Suze Rotolo.^<33><34> As for "Visions of Johanna," "She Belongs to Me" and other songs alleged to have been written about Baez, neither Dylan nor biographers such as Clinton Heylin and Michael Gray have had anything definitive to say one way or the other regarding the subject of these songs.