I am sitting in a diner, listening to Miles Davis’s 1987 album, Music From Siesta. I was managing a record store in Savannah when this album was released three decades ago. Thirty years gone.

It wasn’t the sort of album that we were going to get a promo copy of, at least not at my cruddy little store, so I popped the shrink wrap on the only retail copy we received in our weekly record shipment. This committed me to paying $5.60 after my employee discount–you open it, you bought it. That was 65 cents shy of an hour’s pay for me.

I was 20 years old, and the truth of the matter was that I liked the idea of Miles, but I didn’t really like Miles. Siesta marked the fourth Davis release since I’d started working in record stores a few years earlier. Of the previous three, I’d only heard You’re Under Arrest, and only then because my jazz-loving manager had pulled it out of the defect bin and added to our in-store rotation–a shelf beneath the turntable that held all of the vinyl we were allowed to spin. There beneath the counter, Miles joined John Fogerty’s Centerfield, David Lee Roth’s Crazy From the Heat, Whitney Houston’s eponymous debut, DeBarge’s Rhythm of the Night, The Power Station, Katrina and the Waves, Prince’s Around the World In A Day, and the Hooters.

It never occurred to me that no customer returned You’re Under Arrest due to scratches or warpage, but rather that my store manager wanted to spin Miles’s latest but didn’t want to shell out $5.60 to do so. I was a very trusting boy, and fundamentally an honest one, too. That’s why two years later I’d be on the hook for an hour’s pay for the exact same impulse.

While technically not the last Davis album Columbia released–Aura would come out a few years later after some contractual issues were resolved—You’re Under Arrest was the last in a string of Miles albums the label released between 1955 and 1985.  Thirty years gone.  And so, at age 18 I caught the end of something that I neither knew nor understood.

The cover of You’re Under Arrest was, well, arresting–the blackest man with whom nature had ever graced this sad planet, holding a machine gun (I assumed) as if it were a trumpet at rest. Miles is going to slay you with his music, it promised.

I admired my record store manager, one of a string of father figures I latched onto during my teens and twenties. If he liked Miles then there must be something there, I reasoned, but You’re Under Arrest was, well, not arresting. It was lukewarm, soggy cereal–the kind of music that accompanied community bulletin boards on local television: “Meet TV’s Vic Tayback at this weekend’s Gaffney Peach Festival…the Upstate Stamp Wranglers will hold their next monthly meeting at the downtown library next Wednesday at 7:00….”

Most of the fault lay with me, of course. Caught in the thrall of post-punk, I had no use for instrumental arrangements of Michael Jackson and Cyndi Lauper hits. Hell, I had no patience for Michael Jackson and Cyndi Lauper. Only much later could I bring myself to confess that not only did I like Lauper’s “Time After Time,” but that it was one of the greatest singles of that decade.

Today I must revise that: It’s one of the greatest pop singles of the last three decades. Thirty years gone. But Miles’s version? Not so much. “Time After Time’s” secret sauce is longing, and Davis’s cover contains none of that. It’s just notes on a chart accompanied by washes of cheesy synth, uninspired guitar, and smooth jazz bass noodling.

Regardless, I liked the idea of Miles even if the music wasn’t penetrating my moussed, post-punk noggin. Liking Miles was an aspirational goal, a rite of passage, a sign that I’d crossed some snowy Himalayan pass and entered into a new world. I don’t know what I thought that new world might be–sophistication, taste, adulthood, urbanity, who knows.

Miles wasn’t the only aspirational figure lurking in the bins. I bought Frank Zappa’s Studio Tan for similar reasons. I spun “The Adventures of Gregory Peccary” probably a dozen times in a row, trying to convince myself that I liked it. Three decades later, I own well over 100 Zappa albums and can honestly say that he’s a regular part of my rotation. I can also say that Studio Tan sucks. My Zappa problem came down to nothing more than a poor choice of entry point into his catalog.

The Grateful Dead were another one, mostly because of their artwork. I wore a Blues For Allah pin throughout my 10th grade year without ever actually listening to the album. I didn’t need to: Any album with a cover that good was okay by me. Crossing the Himalayas into the land of the Dead might mark me as a free-spirited, drug munching, hippie artist. That sound pretty good to 15 year-old me, but their albums didn’t. It wasn’t until 1991’s Deadicated: A Tribute To the Grateful Dead that I developed any real appreciation for their music, and that came courtesy of Lyle Lovett’s “Friend of the Devil” and Jane’s Addiction’s “Ripple.”

Making a list of bands that I loved but I wasn’t supposed to love would be simpler than the inverse, but the motivations remained the same. Confessing that as a young, surly post-punk I still secretly spun my KISS albums would have been like confessing that I never crossed the snowy pass outside of my childhood bedroom. Perhaps nothing was more embarrassing to me as a child than proof I hadn’t put away childish things.

I’ve listened to KISS within the last week, by the way.

Anyway, back to a Savannah record store circa 1987. I pulled the new Miles album out of that week’s shipment, and I slit its shrink wrap without knowledge that he was now in his Warner years, that his best was behind him, that true aficionados snubbed his recent work as filler for the suckers, as a cash grab with no more substance than Davis’s recent paintings.

Paintings? What the hell was a jazz musician doing exhibiting paintings? On my side of the Himalayas, an artist could only be one thing. I remained tortured by my decision to compromise and declare myself an illustration major rather than a painting major. The father figures in my life convinced me that if I had to attend art school, I should at least be somewhat practical about it. You’ll never make a living as a painter, kid. Study to be a commercial artist. You’ll thank me later. Commercial or fine art: An artist could only be one thing, unless he was Sam Shepard.

That particular quarter, my illustration professor was focusing on motif and repetition of pattern. He was a very bright man and a very talented illustrator, but his cruel tongue prevented him from becoming yet another father figure. Another cruel tongue was not what I needed three decades ago any more than I need one today. Thirty years gone.

I learned more about composition from that belittling man than I learned from all of my other art school teachers combined. When I pulled Siesta from its box, he was my first thought: the album cover illustration’s strong repetition of the oval from mirror to face to skull; the nautilus-shaped path across the canvas echoed in the figure’s gown; the dressing table and the door moulding both framing the figure and slicing up the canvas. I wanted to run and tell the belittling man that I got it. I’m not certain whether that was the first work of art to drop its robe in front of me, but it’s the first time that I can remember seeing beyond the image’s surface and into the machinery that made it work.

Yes, and the album enclosed might mark the first time that my ears recognized sonic motifs repeated like ovals from mirror to face to skull. I leaned against the glass counter of my little record store, head cleaner and incense inches from my palms, and took in Jason Miles’s synthesizer info, like cold waves crashing against a rocky cliff. Then Davis came in, blew three notes filled with more loneliness and longing than anything I’d ever heard; three notes that would haunt the next 38 minutes like troubled ghosts that could not rest.

I was hooked.

Liking Miles was no longer something I aspired to do, it was something I did. Siesta was the map across that particular mountain pass. From there it was an easy hop to Sketches of Spain, and from that album I could easily navigate back toward his bepop era or forward to his fusion period. A whole new world was mine.

The album’s full title is Music From Siesta. It’s the soundtrack to a movie I’ve never seen, nor will I ever see. I’m sure it’s a fine film, but the album has soundtracked much more important things over the last three decades: bad painting and good lovemaking; profound sadness and inane writing; three decades of Davis, Marcus Miller, Omar Hakim, Earl Klugh, John Scofield, and Jason Miles allowing me to feel transcendent for 38 minutes at a stretch. I don’t need some else’s images cluttering that up.

I don’t know that anyone considers Siesta canonical Miles. Round About Midnight, Sketches of Spain, Bitches Brew, On the Corner–those are the titles that most list as essential Miles. Along the way I’ve picked up all of those and then some. I own Davis’s complete Columbia and Warner output, some of the Prestige era stuff, and plenty of oddball albums issued by other labels, but Siesta remains my favorite. You never really get over your first love.

I’ve even grown to enjoy parts of You’re Under Arrest, though for the most part I still agree with my teenaged assessment of that album. Zappa’s Studio Tan hasn’t gotten any better over time.

I don’t know whether there’s any moral to this other than writing while listening to Miles in a diner makes me melancholy. Perhaps the point is that reaching beyond our current tastes can open up whole new words of interest for us. Maybe it’s time for you to give Miles a chance, or country, or opera. Pack your bindle–it’s time you crossed the mountains before another thirty years are gone.