With Dylan Fest at the Bowery Ballroom in NYC fast approaching, (it’s tomorrow night, Thursday May 27th) I decided it would be a good idea to list the top five Bob Dylan songs with the most confusing, misleading, and otherwise completely random titles. This was no easy task, as Dylan is notorious for his arbitrary track names, and in his extensive catalog there are dozens of candidates. I found it virtually impossible to limit myself to five songs, so please indulge me as I include three “Honorable Mentions” listed below, which just barely missed out on landing a spot in the highly competitive top five, to be named later.

Honorable Mentions:

I Shall Be Free No. 10 – Another Side of Bob Dylan

One of Dylan’s talking blues pieces that were mainstays of his early albums, I Shall Be Free No. 10 is classic rambling Bob at his best. His semi-autobiographical verses in this song feature a challenge of Cassius Clay to a boxing match, and attempting to play tennis in his “high heeled sneakers” with his “wig-hat” falling in his face. I’m still unsure as to the meaning of any of this, but I am sure its highly entertaining, showcasing Dylan’s sense of humor and extensive use of irony. Dylan himself doesn’t help with the explaining either, laughingly singing in the final verse:

“Now you’re probably wondering by now
Just what this song is all about
What’s probably got you baffled more
Is what this thing here is for.
It’s nothing
It’s something I learned over in England.”

It doesn’t make the top 5 however, because somewhere amongst the strange happenings in the anecdotes of this harmonica laden ballad, I assume Dylan is expressing his desire to be free. I’m just not smart/crazy enough to figure out where.

Subterranean Homesick Blues – Bringing It All Back Home

I would argue that Subterranean Homesick Blues was one of the first ever rap songs. During this 2 minute, 22 second roller-coaster ride of a song Dylan spits out rhymes with better flow than Drake, and more charisma than Jay-Z. As a result, this is one of his most memorable and quotable songs, even providing the inspiration for the name of a 1960s radical terrorist organization “The Weathermen,” whose name was cribbed from the line: “You don’t need a weatherman to know which way the wind blows.” Despite all the memorable lyrics, the phrase ‘subterranean homesick blues’ doesn’t even come close to appearing in any of the verses, and for that fact, this song is included on my list as an honorable mention. It misses out on the top 5 however, because the opening line of “Johnny’s in the basement mixing up the medicine” shows subtle connections to the title. These references are primarily that the “basement,” it being a basement after all, by definition is of a subterranean nature, and the “medicine,” I can only imagine, is being “mixed up” as a cure for his homesickness. Touche Bob.

On The Road Again – Bringing It All Back Home

Falling into the category of songs  that are easily recognizable and difficult to name, On The Road Again is, like I Shall Be Free No. 10, a long-winded dissertation on Dylan’s world. Describing an unbelievably absurd setting, its clear this song’s title comes from the narrator’s desire to move away from his ridiculous surroundings. Therefore, while its title is far from memorable, its score on the randomness meter is insufficient to land a spot in the top five.

So there you have the top losers, click here with titles that are guaranteed to drive you completely insane.