Side one "Like a Rolling Stone" {{Listen|filename=Bob_Dylan_-_Like_a_Rolling_Stone.ogg
Highway 61 Revisited opens with "
Like a Rolling Stone", which has been described as revolutionary in its combination of electric guitar licks, organ chords, and Dylan's voice, "at once so young and so snarling ... and so cynical". Michael Gray characterized "Like a Rolling Stone" as "a chaotic amalgam of blues, impressionism, allegory, and an intense directness: 'How does it feel?'" It was suggested that Miss Lonely, the song's central character, is based on
Edie Sedgwick, a socialite and actress in the
Factory scene of
pop artist
Andy Warhol. Critic
Mike Marqusee said the composition was "surely a Dylan cameo", and that its poignancy becomes apparent upon realizing that "it is sung, at least in part, to the singer himself: he's the one 'with no direction home'." "Like A Rolling Stone" reached number two in the
Billboard Hot 100 in the summer of 1965, and was a top-10 hit in Australia, Canada, the Netherlands, New Zealand, and the United Kingdom.
"Tombstone Blues" The fast-paced, two-chord blues song "
Tombstone Blues", driven by Michael Bloomfield's lead guitar, uses a parade of historical characters—outlaw
Belle Starr, biblical temptress
Delilah,
Jack the Ripper (represented in this song as a successful businessman),
John the Baptist (described here as a torturer), and blues singer
Ma Rainey who Dylan humorously suggests shared a sleeping bag with composer
Beethoven—to sketch an absurdist account of contemporary America. Although other interpretations could be put forth: Where once the creativity embodied in the accomplishments of Ma Rainey and Beethoven flourished, now there is stultification of patriotic martial music. For critics Mark Polizzotti and Andy Gill, the reality behind the song is the then-escalating
Vietnam War; both writers hear the "king of the Philistines" who sends his slaves "out to the jungle" as a reference to President
Lyndon B. Johnson.
"It Takes a Lot to Laugh, It Takes a Train to Cry" On July 29, 1965, Dylan and his band resumed recording "
It Takes a Lot to Laugh, It Takes a Train to Cry".
Tony Glover, who observed the recording session, has recalled that Dylan re-worked the song at the piano while the other musicians took a lunch break. Critic Sean Egan writes that by slowing down the tempo, Dylan transformed the song from an "insufferably smart-alec number into a slow, tender, sensual anthem". Gill points out that the lyrics reveal the singer's talent for borrowing from old blues numbers, adapting the lines "Don't the clouds look lonesome shining across the sea/ Don't my gal look good when she's coming after me" from "Solid Road" by bluesmen
Brownie McGhee and
Leroy Carr. The song opens with a
snare shot similar to the beginning of "Like a Rolling Stone". Partially based on
Sleepy John Estes' 1930 song "
Milk Cow Blues", Robert Shelton hears the song as "an earthy tribute to another funky earth-mother",
"Ballad of a Thin Man" "
Ballad of a Thin Man" is driven by Dylan's piano, which contrasts with "the spooky organ riffs" played by Al Kooper. Robert Shelton describes the song's central character, Mr Jones, as "one of Dylan's greatest archetypes", characterizing him as "a
Philistine ... superficially educated and well bred but not very smart about the things that count". The song is structured as a series of ABAB
quatrain verses, with each verse followed by a chorus that is simply a repeat of the last line of each verse: "Won't you come see me Queen Jane?". Gill calls this song "the least interesting track" on
Highway 61, but praises the piano ascending the scale during the harmonica break as an evocation of "the stifling nature of an upper class existence". Others have speculated that the song is directed at Joan Baez and the folk movement, which Dylan had largely left behind. "Queen Jane Approximately" was released as the B-side of Dylan's "
One of Us Must Know (Sooner or Later)" single in early 1966.
"Highway 61 Revisited" Dylan commences the title song of his album, "
Highway 61 Revisited", with the words "Oh God said to Abraham, 'Kill me a son'/Abe says, 'Man, you must be puttin' me on'". As Gill has pointed out, Abraham was the name of Dylan's father, which makes the singer the son whom God wants killed. Gill comments that it is befitting that this song, celebrating a highway central to the history of the blues, is a "raucous blues boogie". "Highway 61 Revisited" was released as the B-side of his "Can You Please Crawl Out Your Window?" single on November 30, 1965.
"Just Like Tom Thumb's Blues" "
Just Like Tom Thumb's Blues" has six verses and no chorus. The lyrics describe a nightmarish experience in
Juarez, Mexico, where, in Shelton's words, "our anti-hero stumbles amid sickness, despair, whores and saints." In this song, critics have heard literary references to
Malcolm Lowry's
Under the Volcano,
Edgar Allan Poe's "
The Murders in the Rue Morgue" and
Jack Kerouac's
Desolation Angels. The backing musicians, Bobby Gregg on drums, Mike Bloomfield on electric guitar, and two pianists, Paul Griffin on
tack piano and Al Kooper on
Hohner Pianet, produce a mood that, for Gill, perfectly complements the "enervated tone" of the lyrics. Heylin notes that Dylan took great care—sixteen takes—to get the effect he was after, with lyrics that subtly "[skirt] the edge of reason". The song opens with a report that "they're selling postcards of the hanging", and adds "the circus is in town". Polizzotti connects this song with the
lynching of three black circus workers in Duluth, Minnesota, which was Dylan's birthplace, and describes "Desolation Row" as a cowboy song, "the 'Home On The Range' of the frightening territory that was mid-sixties America". Shelton suggests Dylan is asking, "What difference which side you're on if you're sailing on the
Titanic?" and is thus satirizing "simpleminded political commitment". although on an early pressing of the single Columbia used another
Highway 61 outtake, "Can You Please Crawl Out Your Window?", by mistake. "Crawl Out Your Window" was subsequently re-recorded with the Hawks in October, and released as a single in November 1965. as well as alternate takes of "Desolation Row", "Highway 61 Revisited", "Just Like Tom Thumb's Blues", "Tombstone Blues", and "It Takes a Lot to Laugh, It Takes a Train to Cry" on
The Bootleg Series Volume 7. released in February 1995. In 2015, Dylan released Volume 12 of his Bootleg Series,
The Cutting Edge, in three different formats. The 18-disc ''Collector's Edition
was described as including "every note recorded during the 1965–1966 sessions, every alternate take and alternate lyric". The 18 CDs contain every take of every song recorded in the studio during the Highway 61 Revisited'' sessions, from June 15 to August 4, 1965. The
Highway 61 Revisited out-takes from the first recording session in New York, June 15 and 16, 1965 comprise: ten takes of "It Takes a Lot to Laugh, It Takes a Train to Cry", six takes of "Sitting on a Barbed-Wire Fence", and fifteen takes of "Like a Rolling Stone". Additionally,
The Cutting Edge contains four instrumental "stem" tracks, lifted from Take Four which was the released "Master take" of "Like A Rolling Stone": Guitar (Mike Bloomfield); vocal, guitar (Bob Dylan), piano and bass; drums and organ. ==Artwork and packaging==