Steely Dan – The Royal Scam

or: the unbearable lightness of being (a Downtown Dude)

Sophomore year of high-school saw my friend Kevin and I living through every Northern Virginian parents’ nightmare: mediocre grades in our foreign language class. We barely escaped Latin 1 with C’s and I was certain whatever little I learned was forgotten over summer break. We needed a miracle.

That miracle glided into our lives on a four-wheeled walker with a perpetually half-cocked grin on his face. Charles Cave, our new Latin teacher, quickly became a living legend in our high-school.

However, in all fairness, I do have to say “Latin teacher” loosely, as I can’t read a line of rudimentary Latin to this day. Mr. Cave was in his 70’s and cut his teeth teaching Latin and Chess to inner-city students in DC. At this stage in his career, Mr. Cave seemed far more interested in shooting the shit with low-maintenance suburban kids then running through cases and declensions.

Mr. Cave charmed everyone he met. He would tell us fantastical stories about a time he got shot in the head and walked himself to the hospital, or how his college football team needed to custom order a helmet for his massive noggin. He would innocuously do a Charleston-style dance next to the cute girls in class as he held his walker. He sent students out the door to fetch hot sink water to stir instant coffee crystals into and for lunch, he ate Hungry Man meals that he let defrost on his desk until they were room-temperature.  He was the coolest fucking teacher ever and every student who had him loved him, so much so that he tripled the amount of Latin sections the school offered the year after he was on the job.

It wasn’t long until the administrative staff started catching on to the farce, and we always tried to subtlety help Mr. Cave out when it appeared he was in professional trouble. When he was being observed, we asked plenty of questions to put up the facade of an engaged classroom. We joined his Latin Club to make it look as though his students really wanted to enrich ourselves in an even deeper level with the era. For our loyal service, it wasn’t long until Kevin and I were in Mr. Cave’s circle of trust, evidenced by him calling us  “Downtown Dudes”.

When Mr. Cave told us we were Downtown Dudes, I’m not sure if any one of us actually knew what it meant past it being a cool turn of phrase. There was very little “downtown” about living in some of the most yuppie suburbs in the entire country, but I liked what it implied. “Dude” is absolutely on the cooler end of the spectrum when it comes to masculine nouns. “Downtown” brings to mind a hipness, a brand of street-smarts and a certain level of worldly wisdom.

But why did I earn such a title? Gun to my head, if I had to tell you what about me as a sophomore in high-school made me a Downtown Dude, my first instinct would be to tell you I listened to Steely Dan.


What can I possibly say about the legendary Steely Dan in 2017 that hasn’t been said countless times before by people much more eloquent than me?

The basics are as follows: Steely Dan was formed in the 1960’s by the songwriting duo of Walter Becker and Donald Fagen, whose career walked the line from actually-good yacht rock to unparalleled jazz rock. Although the line-ups changed, the duo consistently deployed Blackwater-tier mercenaries of rock and jazz to create tightly constructed ballads. Every album they put out didn’t feel like an album at all, but a collection of short stories with just enough sweeping instrumentation and epic solo’s that the listener could fill in the blanks of whatever narrative the band gave you.

One of Steely Dan’s greatest rogue galleries was collected on The Royal Scam, an album which told the stories of unlikable people in lowlife situations. It opens with “Kid Charlemange”the story of failing drug dealer on a verge of irrelevance that is a less inspirational than Kayne West’s sample led people to believe. The triumphant yet ominous strut of the keyboard bounce along with an occasional dissonant note like a fighter shadow boxing himself before twisting his ankle. Kid Charlamange is no hero, but Donald Fagen and his background singers act as his Greek choir and respectfully eulogize his Made In America tragedy.

Another album highlight, “Haitian Divorce”, is a menacing taste of jazz-club tropicália. The whining, seductive guitar drags the protagonist through a marital spat, a scandalous evening out with a mysterious man, and her triumphant return to her husband only to give birth to a baby that doesn’t look quite right. While festive on it’s face, the song moves with the deliberate creep of the end of the night with spilled drinks and bad intentions.

The majority of the other songs on the album are no more optimistic. The Royal Scam provides profiles in theft, crime, loveless sex, adultery and espionage, and as varied as the storylines were, so was the instrumentation. Listening to “Sign in Stranger” sounds like a confident strut into the only saloon in town as a player piano scores your first drink with a bevvy of celebratory flourishes. However on the titular “The Royal Scam”, that same piano is used to a different effect, deliberately ambling along to the tune of a paranoid junkie picking up their pace as if they’re being tailed. 

Like every Steely Dan album The Royal Scam was flawlessly produced, but compared to the rest of their catalog it’s easily the band’s most cynical work. The music projected a weariness and skepticism of the world at large, spoken from the confident, slick voice of Donald Fagen as someone could see all the angles and knew how everything was going to shake out. The voice of a Downtown Dude.


I was hardly a Downtown Dude a year earlier in Latin I, and there’s one specific day where that was made painfully obvious. On it’s face it was a pretty non-descript class, albeit one with a palpable energy in the room with every student trading knowing glances and smiles. At one point during Mrs. Hailey’s lesson, a girl excused herself to go to the bathroom. Five minutes later, a guy did the same, getting a pat from his buddy on his back as he walked out the room. About fifteen minutes later they both arrived back to the majority of the class conspiratorially snickering.

The secret was certainly unbeknownst to Mrs. Hailey. However, it was also unbeknownst to Kevin and me, as  we seemed to be the only students unaware of whatever transpired. As per usual, we were haplessly out of the loop, earning our C by focusing on a competitive round of Advance Wars instead of listening to the lecture.

Weeks after the fact,  I remember hearing tons of rumors the two of them left class to share a joint. Or hook up? Or hook up in exchange for a joint? Or maybe nothing at all. Point being, while our contemporaries were tittering about in the midst of the high-school intrigue happening before them, Kevin and I were clacking away in our own little world on a Game Boy Advance.


So why did a young man, who listened to pretty standard alternative rock like Third Eye Blind, Incubus and the Red Hot Chili Peppers randomly get into Steely Dan?

First of all, it was sarcastic as hell. Steely Dan is famously known for rarely having a “true” love song that didn’t have a dark joke lingering beneath the jazzy tunes. The Royal Scam is no different, featuring a song like “The Fez”The song features a horned up charlatan trying to talk his lover out of having to wear a “fez” on his prick because of his holy prerogative, all as some comically-dramatic Transylvania organs spook in the background. If The Royal Scam is trying to solicit a spit take at any point, this is it.

However, that is a relatively surface-level aesthetic to obsess over. I think the emotional appeal of Steely Dan, particularly The Royal Scam to me at the time was as follows:

As a sophomore in high-school who incredibly far removed from the innocuous, experimental high-school experience of doing drugs and having sex, The Royal Scam was an album that was incredibly post-drugs and post-sex.

Hearing songs like “Kid Charlamange” and “Haitian Divorce” allowed me to feel post-high school in a way that made me comfortable in not participating in even the most innocuous high-school experimentation. In the world of The Royal Scam, drugs and relationships all led to the same forgone conclusion, so perhaps I was in the right all along for not getting invited to “immature” house parties or being bogged down in “doomed” relationships.


In retrospect, I think the reason Mr. Cave is called me a Downtown Dude was because we mutually helped one another “fake it til you make it”. All three years I took his class, Kevin and I helped Mr. Cave maintain an air of legitimacy and keep his job. In exchange, I had straight A’s all the way through Latin IV. Game recognized game, and we both respected each others hustle despite our different stations in life.

To that point, Steely Dan made me feel like a Downtown Dude because it helped me “fake it til you make it” throughout my sophomore year in school. The Royal Scam bestowed upon me an unearned maturity and wisdom in topics where I was too prudish of an outcast to experience myself. Maybe not royal per se, but certainly a scam I pulled on myself to feel more comfortable in my skin.


“I recall when I was small how I spent my days alone, the busy world was not for me so I went and found my own. I would climb the garden wall with a candle in my hand, I’d hide inside a hall of rock and sand.”

Those are the first lyrics that open “The Caves of Altamira”, the only optimistic song on the The Royal Scam. The song opens with a grand, sweeping brass section and immediately segues into Fagen crooning with childlike wonder about exploring a fantastical realm. It’s an interesting curio in not only The Royal Scam, but the entire Steely Dan library, as the grandness, warmth and lack of an ulterior motive completely clashes with a lot of the band’s catalog. In the The Royal Scam especially, “The Caves of Altamira” showed that the Downtown Dude could took only solace in solitude.

I obsessed over this song in high-school. I’d listen to it while I culled heads of romaine and red leaf lettuce alone in the produce back-office of Safeway every Tuesday and Thursday evening after school, instead of doing any extracurricular with friends. I would hear it the back of my head when I stayed home alone in on yet another Friday or Saturday night to play games like The Thousand Year Door and Beyond Good and Evil. If the rest of the album was about feeling tired and dejected of the vices of the world around you, The Caves of Altamira is a triumphant embracing of an inner life in spite of it.

The Royal Scam was a soundtrack for a time in my life where I felt simultaneously detached from a lot of my peers but also tried to feel above it all. It goes without saying that in retrospect, my high-school self-doubt were merely the garden variety anxieties of a narcissistic teenager. I was a nondescript, straight white dude that went mostly unbothered and if I had to guess, people thought I was trying to be cooler than the room by acting so detached. Regardless of the circumstances though, these insecurities brought me to Steely Dan, a band that vastly broadened my taste in music and made me feel like a Downtown Dude when I needed to the most.