A fun industry fact: Have A Cigar was sung by Roy Harper, as he happened to be in the studio and the members of Floyd thought he could be a good fit. Roy Harper is perhaps more known in the mainstream through the Zeppelin song Hats Off to (Roy) Harper than through his own recordings, though he's still alive and active.
Harper didn't feel like he was appropriately compensated for his work on Have a Cigar, which is ironic considering the overall thematic.
I'd argue that Pink Floyd's Comfortably Numb belongs here: AFAIK it's about a band manager injecting the strung out musician with drugs, so he can get up and perform the show that night.
I think the most obvious album to point out which is about many things (including the abuse of the music industry) is To Pimp a Butterfly. I'm surprised I haven't seen it here yet. Even the title is very on-the-nose – the "pimp" in reference is both the music industry and (more frequently) the US government/social structures, and the "butterfly" is a fledgling Kendrick/black rappers/black Americans in general (context depending on the exact song). It's meant to be listened in exact order. Many people say it's overrated but I really disagree. It's an amazing narrative and powerful symbolism with good music.
Hmm songmeanings.com has following opinion about the nirvana song:
Kurt said it himself that this song has no meaning and that it's a bunch of random poetry lines thrown together to a kick ass motherfucking melody. This is one of my favorite Nirvana songs.
Yeah, I'm going mainly by the ironic title to be honest - it always feels to me like Cobain's snarky response to studio pressure to make another Nevermind. I've not looked into closely though, I have to admit.
I think Hank Williams III with the Grand Ole Opry Ain't so Grand deserves a shout-out. Basically a song about how the institution that chewed up and then expelled his grandfather can eat shit.
Porcupine Tree - The Sound of Muzak has one of my favorite lines ever in any song: “Music of rebellion makes you wanna rage, but it’s made by millionaires who are nearly twice your age.”
Oh and somewhat tangential but Hayes Carll I Got a Gig song - "playing for my dinner six nights a week, hurricanes, Easter, and New Years Eve, I got a gig baby!"
There's a good Russian song "The main problem of music in Russia" by Zakhar May
Too Long To Learn Russian: The main problem of music in Russia is that you're listening shit!
Good songwriters can do some good stuff when they are writing what they know. Bad singwriters can crawl up their own assholes, though. Some good Americana Alt-Country ones:
Mercury in Retrograde - Sturgill Simpson takes on the realities of "success". Really the whole Sound and Fury album, though; the whole thing is just him raging at the labels and expectations people put on him as "the next Waylon Jennings."
Bible on the Dash: Life for work-a-day touring musicians. Corb Lund and Hayes Carll actually come up with something useful about a hotel Bible.
What I Really Mean: Wistful realities of road life for someone at a different life phase than the one above.
The Road Goes On & On: a vicious diss track at Toby Keith's expense. REK is like the chill Democrat New-Balance Suburban Dad of brilliant Americana singer-songwriters, so he probably wouldn't speak ill of the dead, but I will. Fuck Toby Keith.
Killpop by Slipknot, that song is amazing. It's very indirect, though, if I didn't read an interview that it's about the music industry, I wouldn't have guessed it.
I can't seem to figure out how to edit my comment on kbin. I thought of one newer than Rush fom a band I've come to enjoy highly and hasn't been posted yet:
Well, some record executives found me one night
I was singin' half-lit, they said it sounded just right (right)
Put my name on an album but they shelved all my songs
Great song about the difficulties of making a living off music now that everything is available for nothing. Father John Misty recorded a version when he was invited to the Spotify Sessions, which was a nice little fuck you to the people inviting him.