I always thought the Freshman was about a guy’s girlfriend comitting suicide after he broke up with her because she was pregnant.
I agree. When this song was first popular, I was dating a girl that was still, technically, married. She was legally separated, so I felt okay about it. Every time I heard this song, it made me think the exact thing that you said.
I’m listening to Filter’s “Take a Picture” right now and I still don’t get it, after many listenings.
“Wake-oh my airpleen, wake-oh my airpleen, my skin is bare, my skin is theirs.”
Is that what I heard??

And no one has brought up perhaps the most confusing #1 song of all time, McArthur Park by Richard Harris. Why did he leave his cake out in the rain?
Tori Amos makes a reference to Neil Gaiman on all of her albums:
Little Earthquakes=Tear in Your Hand “me and Neil will be hangin’ with the Dream King”
Under the Pink=Space Dog “where’s Neil when you need him?”
Boys for Pele=Horses “will you find me if Neil makes me a tree?”
from the choirgirl hotel=Hotel “where are the Velvets?”
To Venus and Back=apparently in a song called Zero Point that didn’t make it onto the album "
Strange Little Girls=Neil wrote the stories for each of the “girls” (personae of the songs on the album)
Scarlet’s Walk=Carbon “Get me Neil on the line/No i can’t hold/ have him read ‘Snow Glass Apples’ /where nothing is what it seems”
Jimmy Webb wrote it but his other hits are nothing like that. A few were “By the Time I Get to Phoenix,” “Wichita Lineman,” “Galveston,” and “Up Up and Away”.
What is Simon & Garfunkel’s Mrs. Robinson* about?
The first verse seems to be about putting someone in a mental institution. “…Look around you all you see are sympathetic eyes. Stroll around the grounds until you feel at home.”
The second verse is about drugs of some kind, presumably Valium. “…It’s a little secret just the Robinsons will bear. Most of all you’ve got to hide it from your kids.”
The third verse is about politics. “…Laugh about it, talk about it when you’ve got to choose. Anyway you look at it you lose.”
The bridge after the third verse for some reason invokes Joe DiMaggio. “Where have you gone, Joe DiMaggio? Our nation turns its weary eyes to you.”
Color me whooshed. 
To understand “Mrs. Robinson,” you have to see the movie The Graduate, which it was written for. It’s about a mom carrying on an affair with her daughter’s fiancé. As for Joe diMaggio, I guess that S&G just threw that in because it was 1968, the country was rioting, youth had rebelled against the Establishment, the Vietnam war was a horrible mess, and everybody was uncertain what was happening to America. Joe diMaggio was an icon of a time when America felt perfectly self-assured.
Hey, that was my 1,970th post. 1970 was the year I was born. I’ll be damned.
I think he wrote this song after a horrible fight with his girlfriend at the time.
I saw an interview with Paul Simon. He said that Mickey Mantle came up and asked him why he wasn’t sung about. Jumin’ Joe was actually old news and MM was the man of the hour. Paul explained why he wrote Joe DiMaggio rather than Mickey Mantle in one word:
Syllables
Re: Uncle Kracker:
I always thought it was about heroin addiction. “…and swim through your veins like a fish in the sea.”
I don’t understand anything Andrew Eldritch was talking about on the Sisters of Mercy Floodland.
"…in the dry season, a lighthouse keeper in the desert sun/ Dreamers & schemers & white treason, We dream of rain in the history of the gun…
the 52 daughters of the revolution turn their gold to chrome/ Nothing to lose, stuck inside of Memphis with a Mobile home"
OK, the last line is a reference to Bob Dylan, but the 52 daughters of the revolution? Gold to Chrome? Come on Andy, lay off the speed.
Rob Zombie in Thunderkiss65.
“Livin’ fast & dyin’ young like a endless poetry/ My motor-psycho nightmare freak out inside of me/ I make it look easy, that’s what I said/ Blast of silence explodes in my head”
WTF is he talking about? It’s some cool word salad on both albums, but I don’t claim to understand it.
Incidentally, those are a couple of my favorite albums from 1988 to 1991. I just enjoy the music, don’t try to make sense of it.
But when Jellyfish covered the song, they introduced it as “probably the sexiest song ever written”.
It’s not right.
Jet was his dog? I didn’t know that. The Martha of Martha My Dear was also his dog.
Is “I Am The Eggman/ I am the Walrus/ koo koo katchoo” supposed to mean anything? And is Simon and Garfunkel alluding to the Beatles song in “Mrs. Robinson” when they too use the “koo koo katchoo”?
“Motor-psycho nightmare” was also a Bob Dylan song, from the album “Another Side of Bob Dylan” (1964). The song is sort of loosely based on the movie Psycho, and includes one of my favorite Dylan lyrics “So I yelled out ‘I like Fidel Castro and his beard!’”
Thanks for the breakdown, Rubystreak… I knew about the first three, but not about the others. Good to know I wasn’t completely nuts! 
Well according to Mr McCartney
“Stairway to Heaven”: the most overrated song in the history of rock ‘n’ roll (by the band that holds the career record for songs about hobbits). It’s pure nonsense.
And it makes me wonder. 