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I would consider Steely Dan, musically, to be a b-tier all time great band. They’re not in most “top 100 artists of all time” roundups, nor are they as iconic or recognizable to the general population as names like, say, Jimi Hendrix or Led Zeppelin for example. And while their music is great, and many of their songs are in my library, I don’t personally place any of them in my top-tier of truly amazing pieces of music.
That said, when it comes to recording, production, and the ultimate results when played with various HiFi equipment, Steely Dan is often cited as the de facto gold standard. That is, when you ask any professional what music you should listen to test and/or assess your equipment, Steely Dan is quite often the answer you’ll get.
And while I wouldn’t put Steely Dan in my personal top tier for leisure/pleasure listening, they are absolutely in my top tier for critical listening, and I regularly use segments of their songs for a/b testing.
Their recordings put great individual emphasis on each instrument. They’d bring in tens of different guitars, for example, for tens of different takes, played by tens of different musicians in some cases, recorded with tens of different microphones, all remixed tens of different times, etc. etc. Point being: they tried really, really, hard to make *every* individual part of their music sound optimal, both on it’s own and as a part of the song as a whole.
One of (if not the) main factors that distinguishes budget headphones from next-level HiFi headphones is clarity and separation. That is, can you hear each instrument distinctly, and does each sound clear or perhaps “real” enough that you can easily focus on its sound specifically. There are certain Steely Dan segments that will quickly show, and much more obviously so than dare I say most other songs, if a pair of headphones is lacking in this department.
Steely Dan songs also have a lot of different instruments that you don’t hear nearly as often in more popular/mainstream music, brass and horns in particular, that are actually recorded and not synthesized.
Another way that cheaper headphones sound audibly short is when certain niche instruments sound kind of off in an unnatural way, like your brain thinks “that’s not how this sounds in real life.” There are many Steely Dan songs in my opinion that will make this shortcoming immediately obvious.