Is Don Henley equating himself with upper-middle-class suburbia in "The Boys of Summer"?

Question

The Boys of Summer by Don Henley contains the following lyrics:

Out on the road today, I saw a DEADHEAD sticker on a Cadillac
A little voice inside my head said, "Don't look back. You can never look back"
I thought I knew what love was
What did I know?
Those days are gone forever
I should just let them go but-

The "deadhead sticker on the Cadillac" is obviously a piece of deliberate irony - owning a Cadillac is a symbol of upper-middle-class suburbia and "deadhead" is a symbol of youthful rebellion.

I'm particularly interested, though, in the line

A little voice inside my head said, "Don't look back. You can never look back"

Is Don Henley implicitly categorizing himself (or, at least, the narrator of the song) as a "Cadillac owner" (minus the Deadhead sticker)? Is the narrator a former "deadhead sticker" type who became a "Cadillac owner" type, warning himself that he's no longer a "deadhead" type?

Answer 1

The song is comparing a failed relationship to the overall passage of time. The first verse describes an empty beach, as all of the beachgoers have left for the summer:

Empty lake, empty streets,
The sun goes down alone.

It then segues into describing the woman he cares for:

I'm driving by your house
Don't know you're not home.
But I can see you,

This is obsessive behavior: he's no longer in her life (so he doesn't know her whereabouts), but he still knows where she lives. It's even creepier in the next verse:

But, baby, I'm gonna get you back,
I'm gonna show you what I'm made of.

He knows, however, he can't have her, and should move on. That's the "little voice inside [his] head".

The key refrain is

I can tell you my love for you will still be strong
After the boys of summer have gone.

"The boys of summer" are baseball players, but the other metaphors seem to refer more directly to the passage of summer itself (and taking the baseball players with it). He continues to love her. The line in isolation suggests devotion even after the fading of youth, but in context, the images point to a relationship that itself is over and he's having a hard time letting go.

The "deadhead sticker on the Cadillac" is another of those supporting images. The owner was presumably a follower of the Dead in their youth, but is now driving an expensive car rather than a beat-up VW Microbus. They retain a little bit of their youthful exuberance after selling out... or perhaps it's mere pretension and a hanging on to a past that, like the boys of summer, have gone.