12 years is a century in the music business. Between his last full player, 2005’s In Flagrante Delicto, with the band All Hours, and his freshly-pressed new record, a jarringly-varied and ambitious musical genesis, dubbed Wry Observer, in which he, well, observes the landscape around him and his scarring unrest, Aaron David Gleason‘s world was flipped upside down. “I overcame some pretty bad clinical depression,” he discloses, forthright. That haze displaced his self-worth and creative drive for the better part of a decade, but it was his tight-knit support system which drove him to rise above it. “I had help. A lot. It fed into this record directly. Writing music was my escape. I must say though, that when I was depressed, I couldn’t really write. I had no spark. When it lifted, gradually, the writing came back,” he tells B-Sides & Badlands, paring the emotional layers of the record, on which he confronts “the fact that I was actually going to have to take ownership of another public display of ‘Me me me…please listen to me.’ I always have mixed feelings about that.”

Gleason turns his heel on shopworn threads of folk, jazz, rock and easy listening, manipulating this coarse but magnetizing drawl across his most honest songwriting so far. “I am such a conflicted person as a writer. I don’t feel like I should make the whole song about myself but at the same time, I can relate to the character or you or whomever, so I bounce between those things,” he says. “I do write more impressionistic songs than, say, ‘let me tell you a story’ songs.”

“A woman past her prime, is that what she’s been saying? I never understand. Is this some kind of game? I never understand. It’s better that you say what you’re thinking,” he sings on “Place in the World,” situating one of the album’s themes of narcissism and feelings of inadequacy against his own listless expedition ⎯⎯ admittedly, he is still nailing down his corner of the world (“Today I feel a bit off. Maybe tomorrow,” he jokes). “Put that bottle down. It’s you that it’s drinking,” he later urges. Wry Observer, brought to life over four days inside Nashville’s Sputnik Sound studio, with the deft handling of producer Brad Lindsay (Two Guns, Keivyn Graves), also inspects matters of jealousy, envy, sexual drive, demon spirits, love and charm. “You know, the good ones,” he quips. His wife, an imperative healing agent and the title song’s stunning inspiration, “made me the writer and human I am now and continue to aspire towards,” he says. “[Our relationship] is my main influence, and she’s my only muse.”

Gleason’s sharp examinations are selflessly transparent. “It shivers in bed like a beast but you feel like it’s not so bad,” he reports on “Nueva York,” a brooding, prayer-like confessional. With opener “The Last to Die in Battle,” he uncages a ravenous story about male fragility, boarded around England’s infamous 15th Century King, Richard III, who reigned for two turbulent years and was accused of murdering his nephews to protect his throne. “Now is the winter of your discontent,” Gleason coos, referencing William Shakespeare’s famous tragedy.

Despite his vocal daring, best focused on such standouts as “The Favor” (featuring Mike Garson), “Pops” and bookender “Brooklyn at Dawn,” he remains quite reserved about his abilities. “Oh, I wouldn’t say I’ll ever be in love with [my voice],” he charmingly scoffs. “But I can get to the point where I think I do alright. Now, it’s about honesty. How honest can I be as a singer?” His gutsiness pours profusely into his emotional arc. Once he gave himself permission to be honest, the narratives and strategic maneuvers clicked into place, as he explains, “First time I ever teared up while recording happened here. That’s that honesty thing. Kind of shocked me.” He adds: “I can’t believe the depth that this album made in four days.”

Gleason’s principal goal was to craft an “American-sounding record,” as he puts it. His efforts paid off, attending to Tom Petty echoes and classic, staunch southernisms. “To those ends, I used open tuning and chose to simplify a lot of my writing,” he notes. The playful jounce between sonic touch points and sentimental density fed his transformation, which was monumental. “I look back and wince, quite often, [at the person I was before this album],” he says. “But who doesn’t? I try to keep my self-referential wincing to a minimum now.”

Gleason is set to play Rockwood Music Hall’s Stage 2 Nov. 14.

Follow Gleason on his socials: Facebook | Website

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