Have a Cigar, Pink Floyd.
Life’s Been Good to Me So Far, Joe Walsh.
Lito Shuffle, Boz Scags.
Jukebox Hero, Foreigner.
Piano Man, Billy Joel.
(Yes, I am old.)
Have a Cigar was the first song I thought of.
“Oh, by the way, which one’s Pink?”
Primus’ rendition is also awesome. https://youtu.be/aEf0SpAEnIc?si=PVfnyKpxFRuslQXo
Not bad, but let me present you with the definitive cover: The Main Squeeze - that solo trounces everything, I’d go as far as, even the original.
I love that some music industry asshole actually asked them that once, and the quote made it into the song.
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.
Reel Big Fish - Sell Out
Tool - Hooker With A Penis
Please play this song on the radio - NoFX
Rockin’ the suburbs - Ben Folds
Dinosaurs Will Die - NOFX
From most favorite, descending:
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Bomb the Music Industry! - Side Projects are Never Successful (punk)
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Backini - Radio (hip-hop)
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They Might Be Giants - Hey Mr. DJ I Thought You Said We Had a Deal (alt-pop)
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Reel Big Fish - Sell Out (ska)
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MC Lars - Download This Song (cross-genre)
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Billy Joel - The Entertainer (pop)
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Barr - The Song is the Single (rock)
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They Might Be Giants - Working Undercover for the Man (alt-pop)
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Ben Folds - Rockin’ the Suburbs (pop)
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David Rovics - The Pirate Radio Song (acoustic punk)
Edited to provide links and genres.
MC Lars - Download This Song (cross-genre)
You’ve reminded me of my answer to this question:
Weird Al - Don’t Download This Song
I see you updated your initial comment to replace Piano Man with The Entertainer (or at least, I don’t remember seeing the latter there before). I’m not sure I like it better than the Weird Al song, but it could give it a run for its money. (I wouldn’t answer Piano Man, which is a song I live, only because IMO it’s not “about the music industry” enough.)
Rounding out my list would be Sell Out by Reel Big Fish, The Load-Out/Stay by Jackson Browne (if it doesn’t have the same problem as Piano Man), and Life’s Been Good to Me So Far by Joe Walsh. That last one is not because I particularly like it, but because it’s the only one that came to mind without having to read other people’s answers.
They Might Be Giants - Rhythm Section Want Ad
They Might Be Giants - We’re the Replacements
They Might Be Giants - the entirety of Venue Songs