Ok, yeah. The era did have plenty of other pop songs with weird structures. Saying it was special for the time was simply wrong, and I apologize.
It’s not that it’s chord progression is weird or anything tonally crazy - it’s a screwy structure, with a weird double chorus and other little catches. It’s not one of those songs where you can learn the progression and pretty much play it on autopilot, and it doesn’t sound like anything but a song you could play on autopilot when you’re just listening to it. When it came to learning it for a cover band I was participating in at work, I was surprised at how odd the structure was, I had to pay attention, and it still came across as a straight ahead pop song. I was a lot more impressed with Springfield afterward.
Contrast this with Toby Keith’s “High Maintenance Woman,” which is thematically somewhat similar but actually does have shades of incel-dom. In that song, a man old enough to not only be working as a maintenance man but to think of it as his career vs. an afterschool job, pines after what he assumes is a high-maintenance woman (because she’s beautiful and rich, I guess), but concludes he can’t ask her out because she wouldn’t date a blue collar guy (because reasons?), yet despite thinking so poorly of her character, he still desperately wants her. There, I can see the seeds of toxic masculinity and NiceGuy-ism germinating. In Jessie’s Girl, I only see the soil where such seeds might be planted, if the guy doesn’t grow up a little before he gets on Reddit.
I think it’s grossly unfair to class someone as a ‘villain’ for having thoughts about a friend’s girlfriend that he doesn’t act on. The song reads to me as a young man who’s jealous of his friend’s girlfriend and probably not sure how to approach the whole dating thing in general. He’s working through the kinds of thoughts a lot of teenagers have, but doesn’t do anything to try to cause his friend to try to break up.
He does say he wants to tell her that he loves her – but the point is prob’ly moot. You can take that to mean he wants a relationship with her where he would eventually tell her that he loves her, but I tend to think it’s meant as right now.
I also see it as a teenage protagonist. I don’t think it necessarily works to put a hero or villain label on him. (Or her. Mary Lambert has an excellent, and more mature, I’d say, cover of it. Interesting how it changes just with interpretive choices.) Teenagers are usually pretty dumb about love in many ways, for many reasons.
One aspect that I don’t like, even more than the omission of her name, is that the relationship is characterized through possession. Jessie’s girl. I want to make her mine. Which of course leads into discussions here about “stealing” a friend’s girl. I know it was the imagery of the time – I’m not faulting RS for using it, exactly. I mostly just want to point out for this discussion that you can’t steal a person. You can be a terrible friend for not respecting your friend’s relationship, or feelings. The girlfriend can betray whatever agreement she has, but, assuming she has agency, she can’t be “stolen.”
Rick (the singer) is just an angsty teenager whining about how his good friend has gotten involved with a really appealing girlfriend and he’s in love with her as well.
“I’ve been funny, I’ve been cool with the lines…” just tells us he doesn’t know what it really takes to attract a girl or guy (i.e. you need more than just that). This is more stereotypical teen drama.
And wishing isn’t pursuing; what we see is that he’s too clueless to go find someone else for himself.
He knows Jessie, but he’s not friends with Jessie. They don’t hang out or anything. Jessie is actually kind of a prick. So how come Jessie ended up with that hot girl he saw hanging off him? Man, he’s thinking, why can’t I find a woman like that? She’s loving him with her body, he just just knows it! Dammit, he wishes that he had Jessie’s girl.