375. "You Can Call Me Al" Paul Simon

"You Can Call Me Al"
Paul Simon
Graceland
1986

I'm starting a new tag for Hall of Fame videos on the countdown (I will go back and add it retroactively to any that qualify from 500-376), and no one would argue that "You Can Call Me Al" is not a Hall of Fame video. You've got a brilliantly simple premise - Chevy Chase, at the height of his douchebag powers, lip syncs the song while Paul Simon sits by, occasionally miming the playing of an instrument. (My friend in 6th grade, when this video came out, was a huge bass nerd, and was apoplectic that Paul Simon looked to take credit for Jaco Pastorius's mind blowing bass solo. I seem to remember him talking about this a lot.)
But the video may actually do a disservice to the song. If you never really listened to the lyrics, the upbeat music, nonsense chorus, and goofball video probably made you think "You Can Call Me Al" is a novelty tune, a sop to Top Forty radio from a Serious Artist.
But check these dubs: this is actually a haunting ode to the creeping mortality of middle age. Our protagonist, the man walking down the street, begins the song wondering why he is "soft in the middle" (and later is called "Mr. Beer Belly"). What follows is a litany of death imagery ("a cartoon in a cartoon graveyard", "Bonedigger, bonedigger""What if I die here?"), and the man laments the loss of his wife and family, and the death (?) of his role model. Finally, in the third verse, our man is a tourist, and finds meaning and salvation in a cathedral's architecture, coming to terms with the finite nature of life, and yelling "Amen and hallelujah!" What seemed on the surface to be a playful confection is revealed to be a meditation on that most universal of subjects: the end.
Also it is funny when Chevy Chase thinks the bongo stand is a side table and drops his glass through it.

376. "Paperback Writer" The Beatles

"Paperback Writer"
The Beatles
single
1966

I wish I lived in the world that this song describes, even if it was never real. This fella is applying to be a fiction writer just like he would apply to be a barista at Starbucks or something. I wonder how interviews to be a paperback writer would go.
Q: Describe an instance in which you were able to resolve a problem outside the three act structure.
A: Um...
Q: Where do you see your protagonist in five years?
A: ....
Q: Do you drink too much and fail to cultivate meaningful relationships?
A: I do!
Q: You start tomorrow.

377. "Missed The Boat" Modest Mouse

"Missed the Boat"
Modest Mouse
We Were Dead Before The Ship Even Sank
2007

Little known fact: in 2008 Isaac Brock converted to Hasidic Judaism, grew dreadlocks and released a hippie-rap record under the name Matismaus.