Bob Dylan is an iconic singer-songwriter who helped to make America stand up and think about the music they were listening to throughout the last four decades.  He is a bard and storyteller of American culture using the guitar, harmonica, and piano as his tools of trade. Known for his nasal-voice, Dylan actually strived for that by emulating an early influence in Woody Guthrie.  Bob Dylan has written hundreds of songs over the past 45+ years.  While this list could be done over and over, my favorite five are below.

Masters of War: The Freewheelin’ Bob Dylan (1963)  Arguably one of Bob Dylan’s greatest social commentaries, Masters of War has an endless appeal because it can be used for any time.  Dylan has claimed that this song is not an anti-war song more than it is a pro-pacifism song.  When he wrote the song, he was referring to Eisenhower’s “military-industrial complex”.  The song is based off of an old English folk song from the late medieval ages called, Nottamun Town.  Dylan picked up from popular tune in Appalachia and changed the lyrics to fit his own sound.

Desolation Row: Highway 61 Revisited (1965)  This song, coming in at more than 11 minutes, was the last track on this album and the only one to not to feature an electric guitar.  Dylan states that this song is a minstrel song fashioned after the carnival singers in blackface that he had seen.  The lyrics provide a warning to people that society is heading towards Armageddon at the height of the Cold War.  The title of the song is a mish-mash of two counterculture favorite novels: Desolation Angels (Jack Kerouac) and Cannery Row (John Steinbeck). Although, it has also been referenced that Dylan took T.S. Eliot’s (mentioned in the song) The Waste Land as an inspiration.  It includes religious, popular culture and Shakespearian references to explain the madness of America in the mid-sixties.

Subterranean Homesick Blues: Bringing It All Back Home (1965)  This was Dylan’s first top 40 Billboard Hit (#39) and one of his first electric guitar songs. It seems like Dylan was obsessed with Jack Kerouac during 1964 and 1965, since this song probably takes its name from Kerouac’s 1958 novel, The Subterraneans, about the Beat culture in New York City.  The song is interesting in the fact that it shows how some youth were joining the emerging counterculture while others were following the establishment in altering verses, yet makes them realize at the end that they are all in the same boat.

Like A Rolling Stone: Single (1965)  One of Bob Dylan’s most recognizable songs, was first released as a single and then put onto the album Highway 61 Revisited.  Of all of his songs, this one cemented his place in the popular music world moving him beyond his folksy roots. The basis of this song came from a short story Dylan had written.  The song is about class division of a rich woman and a poor man (“Napoleon in rags”) who have each fallen from the graces of upper society because they failed to see what was going on around him.  Dylan is explaining that if you aren’t aware of your surroundings, you too, can fall off your high horse into destruction.

Visions of Johanna: Blonde on Blonde (1966) The originally title of this song was, Seems Like A Freeze Out, and was probably a reference to Joan Baez, who Dylan was dating at the time.  The lyrics seem to be somewhat autobiographical of Dylan’s life in entering New York City and his relationships there.  The “visions” are related in lyrical form as wisp-like memories go through the singer’s mind as he is remembering her.