In a recent interview with Stereogum, Ariel Pink admitted to an oncoming sense of occupational malaise, the kind of which affects each and every one of us no matter how enviable your line of work might be. “What’s driving my career as an artist, is that I’m a career artist. People might see me as a hack or whatever. That’s fair enough. But I do what I do. Maybe I would do it anyway, do it differently and perhaps better, and maybe people would love it if I didn’t get any attention. They’d like to believe that I’ve lost something, and I have. I’ve lost an innocence.” Pink’s music has always operated on the fringes of public consciousness, dredging up our discarded mass-produced sounds and revealing the painfully vulnerable, enchantingly individual core at the heart of them, waving the flag of the underground by operating the machinery of the mainstream. But unlike many of his heroes, Pink crossed over. Music became his job. “Maybe innocence isn’t always the goal,” he says. “It’s where you start. But cynicism is the killer of innocence.”

Dedicated to Bobby Jameson marks a dark point in the twisting, unpredictable saga of Ariel Pink. Where his previous album — the delectable, defiantly proud pom pom — captured Pink in a moment of complete self-acceptance, flippantly pissing off journalists and penning ridiculous, masterful songs about white freckles and black ballerinas, his latest record finds him depressed in almost every sense of the word. Ostensibly narrating a saga about the life, death, and rebirth of one Bobby Jameson (a forgotten Californian musician whose world descended into a nightmare of unpaid royalties, drug abuse, and suicide attempts), the album finds Pink disillusioned with his own unexpected fame and success, returning to the well of pop music and finding that its pleasures don’t fulfill in quite the same way that they used to. Of course, there are hooks, and as usual Pink has an uncanny ability to worm his 80s-worshipping melodies and one-liners into your head whether you want them there or not, but the grand effect of Dedicated to Bobby Jameson is that of a restless mind finally beginning to slow down, settling into its patterns rather than excitedly seeking new ones, and struggling with one of the most unavoidable, stinging realities of being alive: disappointment.

The album’s downshift in tone is similarly reflected in its particulars; retreating from the cushy big-label confines of 4AD to the relatively more low-key Mexican Summer, Dedicated to Bobby Jameson is the closest Pink has come to the smeared quality of his earliest albums, trading in studio time with a full band for tracks largely recorded by himself at home. But where his formative material found him delighting in the pure joy of writing songs or taking a perverse fascination in the isolating nature of his home town, Dedicated to Bobby Jameson is littered with unconvincing love songs (“Just Like Heaven”) and neutered cheerleading anthems (“Time To Live”), evoking a sense of going through the motions made all the more dreary by how bright the music seems to want to be but how utterly gray it actually is. Although this contrast between deep-rooted dejection and iridescent songwriting has always been the bedrock of Ariel Pink’s music, here it simply feels as if he’s retreading the same things he’s always known, whether it’s the haunted-house cabaret of “Santa’s In The Closet,” the nostalgic bedroom-folk of “Do Yourself A Favor,” or the saccharine beach-pop of “Bubblegum Dreams.” Nothing here sits among the worst things that Pink has ever recorded to tape, but in its passable comfortability lies a deeper feeling of dread, one that may not be totally apparent on first listen, but one that begins to sink in upon learning more about the album’s mysterious central figure.

Bobby Jameson’s story is a tragic allegory of the promises and pitfalls of the music industry, a familiar tale of the kind of casualties left behind in the wake of late-60s Southern California. A burgeoning young musician who bumped shoulders with the likes of Frank Zappa, The Beach Boys, and Curt Boettcher, Jameson found himself chewed up and spit out by label executives and managers who went from advertising him as the next major voice in pop music to weaseling him out of what little money he stood to make from his largely overlooked recordings. What he ultimately gained the most notoriety for was his disgruntled spiral into alcoholism and criminal activity, which, following years of being presumed dead, Jameson detailed in his own blog, a rabbit hole if there ever was one of one man’s struggle to cope with the ways that life refused to pan out the way he thought it would.

“He was a gnat,” describes Pink in the aforementioned interview. “He was a nuisance. He thought he was a rock star; he just needed to have the right deal come by, and he would just get what everybody else around him was getting… Somehow he was just stuck lamenting about how he never got paid for his first recordings and that just annoys everybody.” Anybody watching one of Jameson’s videos can get the sense for why his bitterness might’ve pushed away anybody whose sympathy he might’ve garnered for his plight, but reading through his blog (which he maintained right up until his death in 2015), it’s difficult to ignore the way that Jameson’s struggles stemmed from an ambition for success that’s absolutely endemic to human nature and from the eventual dissatisfaction and envy that arise when the apparatus of society consistently places that success out of reach. “Music was the horse I rode out on… and the music business was the horse I rode into hell,” reads the header of Jameson’s blog. Even after a lifetime of overdoses, violent outbursts, and broken dreams, his story seems to conclude with one essential, final warning: “The pursuit of fame is as deadly as any narcotic I have ever used.”

That is the ultimate sadness at the core of Dedicated to Bobby Jameson. Whereas Jameson spent an entire lifetime obsessing over his inability to consummate the dreams of his youth, Ariel Pink has actually achieved that kind of success, only to discover how hollow it can be. There are scattered tracks throughout the album where Pink seems to once again take a genuine joy in his craft — the mumbling anti-funk of “Death Patrol,” the silly retro-sleaze of “Dreamdate Narcissist,” the elevator-music breakdown of “Acting” — but its most honest and moving moment comes when Pink directly confronts the depression that suffuses the entire record. “Another Weekend” is one of the most miserable, wilted things Pink has written since “For Kate I Wait,” its liquid keys and acoustic comedown strum providing a legitimate emotional release for Dedicated to Bobby Jameson’s deep sense of emptiness — a feeling of regret that no amount of forced, half-hearted pop songs could possibly hope to absolve.

“I don’t have the same urge or drive to create like I used to,” mused Pink in perhaps the most telling part of his interview. “I just wanted a little bit of love and attention. I didn’t even realize it for 26 years, you know? Then when it came, it was like, aw shit, that’s it?” It’s only natural for one’s drive in life to numb with the passage of time, for the joys of pop music to wane with age. But if Pink were to take one lesson away from the cautionary tale of Bobby Jameson, whose fate in obscurity Pink so narrowly avoided, it should be that relying entirely on the idea of a career in the music industry for fulfillment is a surefire way to end up feeling cheated, hoping and wishing for something that simply isn’t there.