"OTOH" Songs

Sequels that defy their parents.

One of the saddest songs I heard on the radio was “Jessie” by Joshua Kadison. It’s the tale of a dreamer and her lover, caught in what seems like an endless cycle of breakups, makeups, and hasty decisions. You’ve probably heard it sometime:

Jessie, paint your pictures
About how it's gonna be
By now, I should know better
Your dreams are never free
But tell me all about our little trailer by the sea
Oh, Jessie, you can always sell any dream to me…

The song, the lead single on Kadison’s first album, got a video and radio play. It paints a detailed picture itself: Jessie invites the singer to uproot his life and bring his cat Moses to live with her on the Mexico shore. The singer and Jessie have kept trying and failing to make their relationship work, with Jessie’s big dreams never quite materializing in reality. But he’s still in love with her and can’t resist her invitation—even though he knows he’s probably dooming himself to more heartache.

The album had two other hits on it— “Picture Postcards from LA” and “Beautiful in My Eyes”—but I didn’t pick it up, so I didn’t learn until much later about the last song on it, “Georgia Rain.” That song returned to the subject of Jessie—with a very different takeaway!

And Jessie sings soft as the Georgia rain
Comin' down easy on a windowpane
Jessie sings warm as a late-night summer breeze
Hummin’ some faraway tune to the willow trees

At first, you might wonder, Is this a prequel? Are we seeing a moment from earlier in the singer’s life with Jessie? But later lyrics remove all doubt:

There’s a trailer down by the sea
Down in Mexico
We dreamt a lot about it
But we never did go
Some dreams are better from afar
That's just how things are…
And everything's alright
'Cause Jessie's singin' me to sleep tonight

Against all odds, it seems, Jessie and the singer have found the wisdom to make things work between them after all.

Of course, you don’t have to accept both songs into your personal canon. I understand why this song got overlooked compared to “Jessie.” The implied unhappy ending of that song is more resonant, more relatable. But I have to admit, I like the idea of subverting a sad ending to write yourself a better one.

There’s another game of subversion going on with two hit songs from recent years: Bruno Mars’ “When I Was Your Man” (2013) and Miley Cyrus’ “Flowers” (2023).

I should have bought you flowers
And held your hand
Should have gave you all my hours
When I had the chance
Take you to every party
’Cause all you wanted to do was dance
Now my baby’s dancing
But she’s dancing with another man

I can buy myself flowers
Write my name in the sand
Talk to myself for hours
Say things you don't understand
I can take myself dancing
And I can hold my own hand
Yeah, I can love me better than you can

The lyrical similarities don’t go beyond the one stanza, but they sparked a lot of internet debate. Mostly uninformed debate, but that shouldn’t be a surprise on the internet. (No, Redditors, [loud sigh], Cyrus doesn’t owe Mars a songwriting credit.) One song’s about losing a girlfriend through inattention to another guy who treats her better; the other’s about a former girlfriend learning to treat herself right.

I’d love to see a list of “subversion songs” or “OTOH songs” like this. But I might not be the right person to make one. I know it’s a proud tradition in comedy music: some of Weird Al Yankovic’s parodies qualify.

There’s one more odd pair of song videos I can think of, though—odd because I can’t decide if they’re supposed to be related or not. I’ll get into that next time.