Top 25 Albums #18. The Freewheelin' Bob Dylan - Bob Dylan

Bob Dylan's sophomore release pulled off two incredible feats: it succinctly summed up the contemporary feelings of its nation's young people and changed everything. Dylan's eponymous debut contained only two original songs, but Freewheelin' is comprised pretty much entirely of new material, although its melodies are lifted from traditional folk ballads, blues, and spirituals. Its contents (along with its iconic cover image) transformed Dylan from a quirky Greenwhich Village hobo into a superstar singer-songwriter, the "Spokesman of a Generation." As much as he'd come to resent that title, it was true: Freewheelin's songs spoke to the fears and desires of America's youth.

The record begins about as perfectly as any record can. "Blowin' in the Wind" neatly encapsulates all human conflict and strife in a series of elegant questions, posed by a voice wise beyond its years. Each one grasps at the heart of our human weaknesses, from injustice to oppression to war, but Dylan's "answer" is utterly ambiguous; it may sound like a copout, but "Who the hell knows?" seems to me like the only correct response.

While many of Freewheelin's lyrics are ripped straight from the headlines, Dylan wisely included a number of love songs to keep the politics from getting too overbearing. These harmonica-tinged ballads, the first example of which is "Girl from the North Country," balance tenderness, bitterness, and humor masterfully, imbuing them with an endearing emotional realism. "Down the Highway," though a humble blues, is a showcase for the young Bob Dylan's guitar and vocal chops; he even sings some notes in falsetto! Of course, the gosh-darn greatest love song on The Freewheelin' Bob Dylan, and one of the greatest in Dylan's long and fruitful career, is "Don't Think Twice, It's All Right." Finger-picking his acoustic guitar quickly but sweetly, Dylan explains his reasoning for leaving a girlfriend while returning to the title's refrain. Dylan positively nails the tone here, coming off partly as an asshole and partly as a lover who's genuinely fed up with pain and disappointment. He claims both that, "You just kind of wasted my precious time" and "I give her my heart, but she wanted my soul." This folksy little love song is timeless because of its emotional nuance and because said nuance is expressed in a simple and understandable way.

Along with the ballads and "protest songs" such as "Corrina, Corrina" and "Oxford Town," respectively, there are Dylan's forays into surreal humor, my favorite of which is the mostly improvised "Talking World War III Blues." The hilarious track tells the story of Dylan describing a dream to a shrink in which he wanders around a post-apocalyptic town. At the end of the recollection, the doctor tells Dylan that he's been having the same dream. The song is stuffed with memorable lines, one of which calls a Cadillac a "good car to drive after a war." Best of all, though, is the adorable conclusion: "Half of the people can be part right all of the time and some of the people can be all right part of the time, but all of the people can't be all right all of the time. I think Abraham Lincoln said that. I'll let you be in my dream if I can be in yours. I said that."

Proving Dylan's worth as a folk champion, an imaginative poet, and a chronicler of the times, Freewheelin' is the first great achievement in a string of great achievements and a definitive artifact of America's pre-assassination 60's.