Boomer Suicide Anthems

The Who - "Cry If You Want"

There's gotta be a couple Byrds songs that fit this bill, right? 5D maybe?

Rock N Roll Suicide, maybe?

"hold on to 16 as long as you can" is sad as fuck imo

^ cf. "Life goes on long after the thrill of living has gone".

how did we go this long without acknowledging the deadhead sticker on a cadillac

Randy Newman- I'm Dead(But I Don't Know It)

^ cf. "Life goes on long after the thrill of living has gone".

Yeah, that's about as miserable as it gets. The first time I ever heard the song, I think I imagined that the protagonist had become severely disabled in an accident when he turned 20 or something. These songs are interesting imo in that not only do the remembered experiences seem pretty ordinary but nothing extremely tragic seems to have happened afterwards in the lives of the protagonists. Apparently, this sentiment really resonated with a large number of people who were approaching middle age in a time of relative prosperity and stability.

The Statler Brothers have at least a few cuts straddling this line between An Innocent Man/"Pencil Thin Mustache" nostalgia ("Do You Remember These," "Carry Me Back") and boomer suicide, especially "The Class of '57":

Helen is a hostess, Frank works at the mill
Janet teaches grade school and prob'ly always will
Bob works for the city and Jack's in lab research
And Peggy plays organ at the Presbyterian Church

And the Class of '57 had its dreams
Oh, we all thought we'd change the world
With our great works and deeds
Or maybe we just thought the world would change to fit our needs
The class of '57 had its dreams

(obviously, they couldn't be boomers proper graduating high school in '57, so maybe this is some other sub-generational statement of ennui worth noting, but still)

"many rivers to cross"?