Who did it best? Depends on my mood. Just like ice cream.
Lots of people covered this song, includng Joan Baez, who I always thought the tune was about. Got me thinking so I checked Wiki
and it is interesting.
"It's All Over Now, Baby Blue" has been covered many times by a variety of different artists, including Baez, Them, The Byrds, The Animals, The Chocolate Watch Band, Graham Bonnet, Judy Collins, Joni Mitchell, Marianne Faithfull, Falco, The 13th Floor Elevators, the Grateful Dead, and Bad Religion. Them's version, released in 1966 influenced garage bands during the mid-60's and Beck later sampled it for his 1996 single "Jack-Ass". The Byrds recorded the song twice in 1965 as a possible follow up single to "Mr. Tambourine Man" and "All I Really Want to Do", but neither recording was released in that form. The Byrds did release a 1969 recording of the song on their Ballad of Easy Rider album (see 1969 in music).
Dylan's two previous albums, The Times They Are A-Changin' and Another Side of Bob Dylan both ended with a farewell song, "Restless Farewell" and "It Ain't Me, Babe" respectively. "It's All Over Now, Baby Blue" concludes Bringing It All Back Home in consistent fashion. Much speculation has surrounded who or what the "Baby Blue" that Dylan was saying farewell to was. Although Dylan himself has remained mute on the subject, Dylan scholars believe that it is probably an amalgam of personalities within Dylan's social orbit. One person who has been regarded as the subject of the song is folk singer Joan Baez. Dylan and Baez were still in a relationship and were planning to tour together, but Dylan had been growing as an artist and as a person and may have already been planning to leave the relationship. Another possibility is a singer-songwriter named David Blue. A friend or acquaintance of Dylan's from his days in New York's Greenwich Village, Blue is pictured on the cover of Dylan and the Band's The Basement Tapes album wearing a trench coat. Yet another possibility is Dylan's one-time friend, folk singer Paul Clayton. Although Clayton had been Dylan's friend throughout 1964, and had accompanied Dylan on the road trip across the United States on which "Chimes of Freedom" and "Mr. Tambourine Man" were written, by 1965 he may have become more devoted to Dylan than Dylan was comfortable with, and Clayton's use of amphetamines may have made him difficult to be around. However, author Paul Williams, in his book Performing Artist: Book One 1960–1973, counters that "Dylan may have been thinking of a particular person as he wrote it, but not necessarily", adding that the song has such a natural, flowing structure to it, that it could "easily have finished writing itself before Dylan got around to thinking about who 'Baby Blue' was."
medium shot of a woman with long dark hair on left and man playing an acoustic guitar on the right
1963 photo of Joan Baez, left, who has sometimes been regarded as the subject of the song and also covered it, with Bob Dylan, who wrote the song
Another interpretation of the song is that it is directed at Dylan's folk music audience. The song was written at a time when he was moving away from the folk protest movement musically and, as such, can be seen as a farewell to his days as an acoustic guitar-playing protest singer. Dylan's choice of performing "It's All Over Now, Baby Blue" as his last acoustic song at the infamous Newport Folk Festival of 1965, after having had his electric set met with boos, is often used as evidence to support this theory. That particular performance of the song is included in Murray Lerner's film The Other Side of the Mirror.
Yet another interpretation is that Dylan is directing the farewell to himself, particularly his acoustic performer self. The opening line "You must leave now" can be a command, similar to the line "Go away from my window" that opens "It Ain't Me, Babe". But it can also be an imperative, meaning just that it is necessary that you leave. And the song is as much about new beginnings as it is about endings. The song not only notes the requirement that Baby Blue leave, but also includes the hope that Baby Blue will move forward, in lines such as "Strike another match, go start anew". If Dylan is singing the song to himself, then he himself would be the "vagabond who's rapping at your door / standing in the clothes that you once wore". That is, the new, electric, surrealist Dylan would be the vagabond, not yet having removed the "clothes" of the old protest singer. Alternatively, the vagabond and "stepping stones" referenced in the song have been interpreted as Dylan's folk audience that Dylan needs to leave behind. He would also be telling himself to "Forget the dead you've left, they will not follow you." Others he may be saying farewell to in the song are any of the women he had known, the political left or to the illusions of his youth.[10