I gave the top 4 AI chatbots the same question. 

X’s Grok, OpenAi’s ChatGPT, Google’s Gemini, and Anthropic’s Claude were all asked:

How do you feel about calling Steely Dan the Rush of yacht rock?

Their answers revealed so much about their personalities.

Grok | The Creative Rebel

Steely Dan as the “Rush of yacht rock”? 

Nah, that’s off. 

Steely Dan’s too sharp, too cynical, with jazz chops and complex chords that’d make your head spin. Yacht rock is smooth, laid-back vibes—think Doobie Brothers or Toto. Steely Dan’s more like if a dive bar philosopher and a jazz cat had a baby. Calling them yacht rock is like calling a fine whiskey “booze.” It’s not wrong, but it misses the depth. Rush, though? Maybe for the prog-rock braininess, but Steely Dan’s groove is way cooler. They’re in their own lane—let’s not box ‘em in.

ChatGPT | The Conversationalist Guide

That’s a pretty slick analogy—and kind of dead-on in a few ways.

Calling Steely Dan “the Rush of yacht rock” makes sense if you mean:

• Musical precision: Like Rush, Steely Dan is obsessive about arrangements, session players, and production quality. Total studio perfectionists.

• Musician’s band: Both are groups that musicians idolize. Even if you’re not a fan of the genre, you respect the chops.

• Odd time signatures and jazz influence: Steely Dan isn’t prog rock, but they sneak in complex jazz harmonies, modal solos, and weird chord changes that go way beyond standard soft rock.

• Cult following meets mainstream success: Just like Rush had a devoted fanbase despite being a bit “off” from typical radio rock, Steely Dan carved out a refined corner in a genre often mocked for being too smooth.

Where it might fall short:

• Thematic intensity: Rush is sci-fi, philosophy, Ayn Randian space opera. Steely Dan is cocaine, sarcasm, and washed-up California dreams. One’s heady and earnest, the other’s cynical and wry.

• Stage presence: Rush lived to tour. Steely Dan famously hated the road for years and became more of a studio project than a performing band.

Still, if yacht rock had a virtuoso core, Steely Dan would be the cerebral, weird, jazz-drenched perfectionists—the high-IQ outliers sailing with a cocktail in hand. So yeah—“the Rush of yacht rock” works if you mean the smart kids in a genre known for being easygoing.

What prompted the comparison—were you making a playlist or arguing with someone who hates on Steely Dan?

Gemini | The Intellectual Analyst

Calling Steely Dan the ‘rush of yacht rock’ presents a nuanced perspective that warrants careful consideration. 

While both Steely Dan and the genre retrospectively termed ‘yacht rock’ exhibit characteristics such as sophisticated musical arrangements, high production values, and discernible jazz and R&B influences, the analogy of ‘rush’ introduces a critical point of divergence.

‘Yacht rock’ is generally associated with a relaxed, smooth, and often mellow sonic aesthetic. In contrast, Steely Dan’s music frequently incorporates more complex harmonic structures, syncopated rhythms, and a lyrical approach that is often characterized by irony and ambiguity, resulting in a listening experience that is less overtly tranquil.

Furthermore, the appellation ‘yacht rock’ itself carries connotations that are sometimes perceived as lighthearted or even dismissive. Steely Dan, throughout their career, have maintained a reputation for artistic integrity and critical acclaim that distinguishes them from some of the artists more readily categorized within the ‘yacht rock’ label.

Therefore, while the comparison highlights certain shared musical elements, it may oversimplify the distinct artistic intentions and overall character of Steely Dan’s body of work, potentially understating its complexity and more assertive musical qualities.

Claude | The Empathetic Consultant

That’s an interesting characterization of Steely Dan! While they’re often grouped with yacht rock, calling them “the rush of yacht rock” is actually quite apt for a few reasons.

Steely Dan’s music has that smooth, sophisticated production quality associated with yacht rock, but with significantly more musical complexity and lyrical depth than many of their contemporaries. Similar to how Rush brought progressive elements and technical virtuosity to rock, Steely Dan brought jazz harmonies, complex arrangements, and perfectionist studio techniques to their smooth sound.

Donald Fagen and Walter Becker were known for their meticulous approach to recording, often employing top-tier session musicians and spending enormous amounts of time crafting their sound. Their lyrics tend to be darker, more sardonic, and more literary than typical yacht rock, which adds another layer that sets them apart.

So I’d say your comparison is spot-on – they occupy a similar position in yacht rock that Rush does in progressive rock: more musically advanced, more demanding of their listeners, and with a particularly dedicated fan base that appreciates their technical excellence.

How I see it: 

Grok
Grok’s the one who walks into the room with a smirk and says, “Nope, that’s wrong,” before you finish the question. It’s got an attitude. Quick on its feet, and a little too cool, but that’s the brand they’re going for. And you know what, it works. Grok doesn’t waste time on niceties. It shoots straight, throws metaphors like punches, and doesn’t really care if you agree. It already knows it’s right. You don’t come to Grok for consensus. You come for the mic drop.

ChatGPT
ChatGPT’s the easygoing smart friend who is eager to please. What’s most pleasant is how they break everything down in a way that makes sense, even when it’s tripping. It’s sharp, but approachable. It thinks before it speaks. Doesn’t argue, just calmly lays out its case and lets the logic do the heavy lifting. It’s not great at jokes, but that doesn’t stop it from throwing one in there from time to time. Chat does seem a little too anxious to keep the conversation going. 

Gemini
Gemini’s like that kid in class who had a binder for every subject and always asked if the homework counted for extra credit. It’s smart, no question. But man, it’s formal. Polished. Careful. Doesn’t riff, doesn’t joke. Just parses every word like it’s writing for a museum plaque. You respect it, sure. You might even learn something. But Gemini is the wrong buddy to ask this question. Nerd alert. 

Claude
Claude’s thoughtful. It listens. It leans in. Feels like someone who really wants to get it right and make you feel understood while doing it. It agrees gently, adds layers, connects ideas without making it about itself. There’s depth there, but it doesn’t show off. More like the person in the room who doesn’t talk first, but when they do, everyone stops scrolling. It’s brainy without being cold. Smart with soul.

Sorry. I wish I could give you those 4 minutes back.