The first side of Freewheelin’ definitely outweighs that of its latter half. The opening trio alone, consisting of “Blowing,” “Girl From the North Country,” and “Master of War” remain three of Dylan’s finest achievements. Add to this the one-two punch of the record’s two blues tracks, “Down in the Highway” and “Bob Dylan’s Blues.” Finally side A ends with the apocalyptic “A Hard Rain’s A-Gonna Fall,” a song that has remained a steady part of Dylan’s live repertoire and has seen many different incarnations over the years, most notably circa his Rolling Thunder Revue days. When Dylan sings “Where hunger is ugly, where souls are forgotten / Where black is the color, where none is the number,” it’s clear this young songwriter from Bleecker street is a voice to be heard.
Originally envisioned as a blues record entitled “Bob Dylan’s Blues,” Freewheelin’s second half features the majority of the album’s exercises in simple, folk style blues.
With the exception of “Don’t Think Twice It’s Alright,” which, combined with “Girl From the North Country,” shows Dylan’s knack for writing emotionally triggered love songs, side B at times feels like a more polished/original extension of Bob Dylan.
Whereas Bob Dylan consisted of only two original songs amidst a collection of covers and traditional folk songs, Freewheelin’ is Dylan breaking out of his shell. Only two traditional covers–“Corrina Corrina” and “Honey Just Allow Me One More Chance”–are featured on the record and are ultimately the album’s two forgettable tracks. The remaining eleven songs introduce a confident and assertive Dylan whose songs range from tender to poignant, tragic to playful.
The album’s closer, “I Shall Be Free,” returns to a bit of the humor found on Bob Dylan but maintains Freewheelin’s political timeliness. Opening with the line, “Well I took me a woman late last night / I was ¾ drunk, she looked alright” and eventually culminating with a fictionalized phone call with President Kennedy asking, “Bob, what do we need to make the country grow? I responded, Brigitte Bardot,” it’s obvious that Dylan’s tongue is in his cheek.
Freewheelin features some of Dylan’s finest songs and would have been a monumental debut for this rising musician. Many of the tracks would receive various makeovers throughout his touring years. “Girl From the North Country” would later be re-released as a crooning duet with Johnny Cash on Nashville Skyline, not to mention a musical doppelganger on The Times They Are A-Changin’s “Boots of Spanish Leather.” “Hard Rain” transferred flawlessly to Dylan’s gypsy electric phase in the early 70s, and “Don’t Think Twice It’s Alright” remains a staple encore set piece for Dylan’s current Never Ending Tour.
As a whole entity, the album’s overall focus is never truly defined but rather the collection of songs seem to be introducing audience to a new side of Bob Dylan (a rebirth formula he would ultimately use again, and again). The two covers feel tossed on last minute, while a number of B-side tracks from the album (later released in the Bootleg Series 1-3) would have been right at home on this release. Overall we get Dylan the bluesman, Dylan the romantic crooner, and for the first time in his career, Dylan the activist, a role that would play a crucial role in his following release, The Times They Are A-Changin’.
Key Tracks: “Blowing in the Wind,” “Girl From the North Country,” “Masters of War,” “Don’t Think Twice It’s Alright,” “I Shall Be Free.”