Jackson Browne’s “Rosie”. It was several years before it occurred to me that Rosie was not his girlfriend.
I thought that line was:
Well I know what I am, and
IN BED I’M A MAN and so is Lola…
So, my take on the song is that some guy is out one night and picks up what he thinks is a woman. He has some reservations (I can’t understand why she looks like a woman and talks like a man) about Lola’s gender identity.
But…after some champagne…he ends up in bed with what presumably is a drag queen (or a bisexual cross-dresser - it’s hard to tell), and comes to grips with it.
“Follow Me”, by Uncle Cracker.
Somehow that ended up as the theme song of my sixth-grade class. We sang it all the time. I couldn’t quite make out all the lyrics, but I thought it was sweet that he didn’t “care about the things you wear”. He loves even when she dresses frumpy!
I’m not sure when I realized that it was “I don’t worry about the ring you wear”, but I was shocked, shocked to realize the class song was about adultery.
The aforementioned Papa Was a Rolling Stone and Dylan’s Like a Rolling Stone I thought were about the band The Rolling Stones. In my mind it made sense…
I always wondered why the chorus to Bon Jovi’s Livin On A Prayer was so odd. Here’s how I heard it;
She says we’ve got to hold on to what we’ve got
Cause it doesn’t make a difference
If we’re naked or not
We’ve got each other and that’s a lot
For love - well give it a shot
Whooah, we’re half way there
Livin on a prayer
Take my hand and we’re naked I swear
Livin on a prayer
Heh…I always hear this as “be poised and quiet”, which struck me as a totally non-sequitur for a song about love.
This isn’t like the rest of the posts, but I think it fits: when I was young, maybe 8 or so, I was on a family car trip and “Georgia” by Ray Charles came on the car radio. I asked if the song was about the state or about a woman named Georgia. All the adults burst into laughter about how naïve I was.
I still think it was a good question.
I’ll do you one better. My best friend thought it was “four hundred children dropped in a field.” He pictured a bunch of kids with parachutes.
Heh. That is really sweet. I’ll second the poster who said they giggled at this. It totally reminds me of Ramona Quimby (Beverly Cleary books) who thought that “Dawn’s early light” was “Dawnzer lee light” and figured that a Dawnzer was some kind of lamp.
That is hilarious, and reminds me of my Beatles confusion.
In “Yesterday”, I understood the lyric to read:
This always bugged me: Why did he say “Something wrong” when he should’ve said “Something’s wrong”? The grammatical error would drive me nuts! 
Cherry Hill Park…what kind of games did people play outside after dark, anyway?
“Total Eclipse of the Heart” has a line that always perplexed me, until I was older and heard part of it more clearly:
I don’t know what to do and I’m always in the dark
We’re living and have power - I can get up and spazz!
(It didn’t help that in the video she was sort of tearing at her hair at that part.)
I had no idea what this meant. I vaguely thought it was some kind of metaphor that meant she was so overwhelmed by the power of their love that she could just flip right out, or something. I was never totally sure because I couldn’t quite hear the words properly.
Years later I made out the words “powder keg” and thought “powder keg?” WTF? Then I deduced that “spazz” was “sparks” and then I was all:
“Oooooooh, that’s what she was saying… That’s not much better actually.”
Five Short Minutes by Jim Croce
I didn’t know a rock groupie calling herself Cynthia Plaster Caster made casts of rock musicians dicks.
I wonder if she has a cast of Jim Croce’s dong on a shelf? She has a web site.
http://www.cynthiaplastercaster.com/
I like The Beat Farmer’s take on it:
‘Four ugly children and a crotch that won’t heal’
When did Paul die?
I just thought of another Fleetwood Mac song I didn’t understand: Rhiannon. As a 12-year-old in 1976 rural Kentucky where everyone was named Lisa, I had never heard the name Rhiannon and wouldn’t have believed you if you’d told me it was a name. Anyway, I thought they were singing —
*Would you stay if she promised you Heaven?
Will you ever win? Will you ever win?
Will ya evvvvvvvvvaaaaaaah?
Wi’ ya evvvvvvvvvvvahhhhhhh-uhhhhhhh?
Will ya evvvvvvvvvaaaaaaah?
Wi’ ya evvvvvvvvvvvahhhhhhh-uhhhhhhh?*
ZZ Top song “Tush”
Even into adulthood, I thought the line
I said lord take me downtown, I’m just looking for some tush.
was
I said lord take me downtown, I’m just looking for some touch.
I thought it was “Be quiet, don’t cry”…and I thought the song was “I’m Not Alone.”