She discussed her upbringing as a "red diaper" baby; a child of Communist Party USA members during the McCarthy Era.

At about the time she met Dylan, Rotolo began working full-time as a political activist in the office of the Congress of Racial Equality (CORE),[citation needed] and the anti-nuclear group SANE.

[1] Describing their meeting in his memoir, Chronicles, Volume One, Dylan wrote: Right from the start I couldn’t take my eyes off her.

Cupid’s arrow had whistled past my ears before, but this time it hit me in the heart and the weight of it dragged me overboard... Meeting her was like stepping into the tales of 1001 Arabian Nights.

[12]It was not until they met that Dylan's writing began to address issues such as the civil rights movement and the threat of nuclear war.

[13]Rotolo left New York in June 1962, with her mother, to spend six months studying art at the University of Perugia in Italy.

[15] Dylan's separation from his girlfriend has been credited as the inspiration behind several of his finest love songs, including "Don't Think Twice, It's Alright", "Tomorrow Is a Long Time", "One Too Many Mornings", and "Boots of Spanish Leather".

Dylan also credited her with interesting him in the French poet Arthur Rimbaud, who heavily influenced his writing style.

In Chronicles, Dylan describes the impact of the song "Pirate Jenny" while attending a Brecht show on which Rotolo worked.

[3][20] Their relationship failed to survive the abortion, Dylan's affair with Joan Baez, and the hostility of the Rotolo family.

Remaining politically active, Rotolo joined the street-theater group Billionaires for Bush and protested at the 2004 Republican National Convention in Manhattan.

In November 2004, she made an unannounced appearance at the Experience Music Project, on a panel discussing Dylan's early days in Greenwich Village.

Perhaps an inherent contradiction is the problem: she’s writing about her unwillingness to be defined by her relationship to a famous man, in a book with Dylan on the cover.

[7]The Guardian, too, notes that Rotolo is defined as "the girl with the wistful eyes and hint of a smile whose head is resting on the suede-jacketed shoulder of a nice-looking young man as they trudge through the snow on the cover of 1963's The Freewheelin' Bob Dylan."

The review agrees with the New York Times's comment ("a disconnected list") that the book is "oddly organised", but at once adds "though not as random as it seems".

The scene in which Robbie and Claire run romantically through the streets of New York re-enacts the cover of the 1963 album The Freewheelin' Bob Dylan.

[27] In the 2024 biographical film A Complete Unknown, Sylvie Russo, a fictional version of Rotolo, is played by Elle Fanning.