The Heartbreaking Songs of Mac Miller: A Reflection on Life and Loss

Ryan S. Gladwin I’ve found myself over the past year going in circles through Mac Miller’s discography, discovering, listening, and then re-listening to everything and anything by him I could find. With the announcement of...

Ryan S. Gladwin

I’ve found myself over the past year going in circles through Mac Miller’s discography, discovering, listening, and then re-listening to everything and anything by him I could find. With the announcement of his first posthumous album, "Circles," I’ve found this cycle repeating itself more than ever.

You can’t help but draw new meanings from some of his previous lyrics. The Pittsburgh rapper spoke about death, drugs, and depression throughout his career, but no one imagined we would be reflecting on these songs like we are today. Here are four heart-breaking songs from the late rapper.

Best Day Ever

The music video for "Best Day Ever" opens with a clip of Malcolm as a child, rapping The Sugar Hill Gang song ‘Rapper's Delight’. The innocence and childlike wonder you see the rapper filled with are soul-destroying to witness, knowing his fate.

A fresh-faced Mac Miller is hungry to take on the rap world in this song. There was little expectation of what he should or shouldn't do, or where he should or shouldn't go. He was stress-free. The rapper said he was ‘just trying to capture a happy and positive vibe’ with this song, and that’s exactly what he did.

No matter where life takes me, find me with a smile.
Pursuit to be happy, only laughing like a child.
I never thought life would be this sweet,
It got me cheesin’ from cheek to cheek.
—Mac Miller - Best Day Ever

The hook captures the joy Mac Miller radiated throughout his life. It feels like the perfect tribute to the late rapper, so it is fitting that it closed his ‘Celebration of Life’ - a tribute concert used as a final goodbye for friends, family, and fans.

Grandpa Used to Carry a Flask


In 2013, Mac dropped a mixtape under his alter-ego alias Delusional Thomas, where he would explore the darker side of his mind. In the closing track, "Grandpa Used to Carry a Flask" (featuring Mac Miller), Thomas is portrayed as the devil on Mac’s shoulder, showing a power struggle between the two. It appears that Mac is starting to give in to the evil in his life.

Thomas kicks off the song by keeping to his name and confiding in ignorance, a motif in Malcolm’s work. He clearly knew he had a drug issue, but he just couldn’t face it - Thomas personified that.

So we close our eyes, hoping we forgot to die.
Shit, it must have slipped my mind, why?
—Delusional Thomas (Ft. Mac Miller) - Grandpa Used to Carry a Flask

In Mac’s verse, he draws comparisons of himself to his Grandpa. As the song title suggests, his Grandpa always had alcohol with him, just like how Mac will always have drugs - he likens this dependence to being caught on a leash. He finishes his verse by admitting that every night he closes his eyes, fearing he won’t wake.

Thomas sadistically comes in to say he doesn’t care what happens due to his drug use because the worst that can happen is he will die. This is then juxtaposed by a back and forth between Mac and Thomas, revealing that they are the same person. Thomas doesn’t care about Mac, he doesn’t even care about himself.

Perfect Circle/God Speed

In the first half of the track, "Perfect Circle," Mac talks broadly about his issues with drug use in an almost shameful braggadocious way, with the haunting piano looming over his bars. It makes you feel like you are in a western movie waiting for a shoot-out to happen - the shoot-out being Malcolm’s ultimate demise.

Then a phone rings out, leading to a real voicemail from his brother that was left after not hearing from the rapper for days over the Christmas period. Malcolm said, “I wanted to tell the story of a lower point and my brother trying to get me out of it.”

They don’t want me to OD and have to talk to my mother.
Tell her they could have done more to help me and she’d just be.
Crying, saying that she’d do anything to have me back.
—Mac Miller - Perfect Circle / God Speed

Soon after the interlude, Mac spits some of the eeriest lines I’ve ever heard in a rap song. He predicts that he will go out due to an overdose. He sends a warning to those who regret not helping him enough. Just after saying ‘everybody’ is trying to get him to go to rehab and a voicemail of his brother trying to help. It is clear people were trying to support him; he was just blind to it. The rapper goes on to admit that he knows what he is doing is a problem and that he knows he will die if he doesn’t change.

The track ends optimistically, with the rapper seeming to have turned a page and waking up to his issues - ‘Good morning,’ the rapper says. It’s just a shame that the exact issues Malcolm spoke about in this track are the same that led to his death.

So It Goes


The closing track to the final album Mac Miller ever dropped was always going to be a monumental moment in his discography, but there is more to this track than meets the eye. The title of the track ‘So It Goes’ is repeated throughout the song, a phrase lifted from Kurt Vonnegut’s novel ‘Slaughterhouse-Five’. The phrase appears anytime a death occurs in the book, showing how death is inevitable and the world will keep on spinning despite the death of somebody - this adds a darker meaning to the song. With the context of Mac Miller’s death, it is eerie that the last track of his final album was titled after a phrase about the inevitability and meaninglessness of death.

Nine lives, never die, fuck a heaven, I’m still gettin’ high.
Never mind, did I mention I’m fine?
'Cause her pussy gettin’ wetter when the weather dry.
—Mac Miller - So It Goes

Mac talks about his disregard for his health because he is high and diverts attention away from the fact he's drugged up by assuring the listener he is fine, and then moving onto sex. He talks about how he can’t find satisfaction from anything, and this might be the reason why he continued to turn to drugs.

However, maybe the most haunting thing about this song is a deleted tweet from the rapper saying how he wanted the instrumental sequence at the end of the track to sound like an ascension to heaven. To make things even eerier, Mac Miller's last Instagram story, posted the day he died, was of the end of this song. It’s almost as if he knew.

As we reflect on the heart-breaking songs of Mac Miller, the rawness of his lyrics and the emotions he poured into his music become even more apparent. His legacy lives on through his art, forever reminding us of the complexities of life and the struggles many face.