Mac Demarco’s relationship with his father is a thorny one.

On the first track of his breakout 2012 album, 2, one of the first things Mac Demarco does is call his dad the “pride of the neighborhood”, his low voice drenched in sarcasm. He depicts his father as a lazy slob, detached from his family, spending his time either drunk on the couch or manufacturing drugs in the basement. All of this is painted in broad strokes, Demarco doesn’t quite cut deeply or enough to directly confront these feelings of disaffection. This hesitation is evident in the song’s chorus, which hints ever so subtly that Demarco is still unable to let go of the anger he has for his dad’s actions: “Oh life moves so slowly / Oh just try to let it go.”

In his 2014 Pitchfork profile, Demarco provided some background on this fractured relationship. His parents never married, and his father, an alcoholic and an addict, left without paying child support when young Mac was 5 years old. His father hasn’t been entirely absent from the singer-songwriter’s adult life — they’ve met again a handful of times — but Demarco’s struggle to come to terms with his family history has maintained a vague thematic presence in his songs. Yet, somehow, this issue has never gotten a proper, straightforward lyrical confrontation. In the same Pitchfork profile, Mac’s mother Agnes sympathizes: “What do you say to a father who you know chose alcohol and drugs over you?”

That’s not to say Demarco hasn’t gotten really close to moments of genuine emotional reckoning in his songs. In “Chamber of Reflection” from 2014’s Salad Days, he meditates on what it means to truly see oneself in moments of uncertainty and identity crisis: “No use looking out / It’s within that brings that lonely feeling”. Each cycling repetition of “Alone again / Alone again” in the song’s refrain reinforces an image of Demarco descending deeper and deeper into his own psyche, into a hall of mirrors and memories.

“My Old Man”, one of two new Mac Demarco songs released yesterday, finally gives his listeners a glimpse of what he was seeing in that chamber of reflection. “Look in the mirror / What do you see? / Someone familiar / But surely not me.”

Demarco has always been interested in reflections of himself, from “Chamber of Reflection” to the cover of his debut album Rock and Roll Night Club (2012), where he’s pictured looking into a shard of a mirror, messily smearing on deep red lipstick. On past albums, he’s used prominent vocal effects, separating the recorded voice in his songs from his own self, creating yet another distorted likeness. “My Old Man” is noticeably absent of any of these woozy effects. Here, he’s speaking directly to the listener, as himself, laid bare.

The song begins with a goofy little synth pattern and a light-hearted acoustic guitar chord progression, giving the impression of a more typical Mac track, the light stuff that got him his legions of dad-hat-wearing young fans and labels like “chill” and “slacker”. But it only takes him a few lines to shut all that fun down: “Look how old and cold and tired and lonely he’s become….There’s a price tag hanging off of half of all that fun.” Those lyrics are Demarco’s most direct admission yet of something his fans have seen for a while: his non-stop chain smoking of Viceroys, his copious drinking, and his endless touring have taken a physical toll on the songwriter. He’s 26 years old, and looks at least 35.

All this comes before the song’s kicker of a chorus: “Uh-oh, I’m seeing more of my old man in me / Oh no, I’m seeing more of my old man in me” The context of this despairing admission within the song is gut-wrenching, but it’s especially heartbreaking when you know the story of Demarco’s early life. “My Old Man” is the sound of the singer coming to terms with his physical and emotional similarities to the person who hurt him the most in his life.

“My Old Man” is the closest Mac Demarco has ever gotten to writing a Paul Simon song, and that’s just about the highest praise anyone could ever give a songwriter. It’s uncomplicated, hits all the right emotional notes, shows off clean production, and has subtle, perfect instrumentation. That’s definitely not to say we’re about to get a Graceland-level classic from Demarco’s upcoming LP, This Old Dog, because that’s never, ever, ever going to happen. But maybe it wouldn’t be a stretch to say that this album could be his Hearts and Bones.

Before this track was released, I don’t think anyone expected much from Mac Demarco’s new material. I certainly didn’t. With a rabid teenage fanbase that will likely sell out his tours until the end of time, there doesn’t seem to be any demand at all for Demarco to get introspective, let alone emotionally heavy at this point in his career. This sudden lack of pressure seems to have had the opposite effect, bringing Demarco out of his “slacker” comfort zone. It gave him the time to breathe, to take a long look at his own reflection, and to write this song, his best and most emotionally resonant work in years.

Written by Matt Sater