Some of the early critiques of Mac Miller weren’t entirely unfair. His first few projects were lined with too many songs that mixed and matched the same one-note themes and first-thought wordplay, and he wasn’t immune to the awful trend of the era of reaching for obvious, obnoxious samples and letting them do the heavy lifting (the “Fireflies” edit on “Don’t Mind If I Do” is particularly egregious). Still, Mac was already more thoughtful than many of his would-be peers who would define the turn-of-the-decade white rapper archetype. He was too earnest to be compared to a smug outsider like Asher Roth but far too self-aware to fall into the same traps Macklemore caught himself in.

The difference between Mac and a million was his studious approach, how he seemed in love with the shapes his flows learned to make, rather than ever treating the art form as a means to an end. In a song like “Kool Aid & Frozen Pizza”, the sincerity of his reverence for rap history was evident, both in the golden era nostalgia of his bars and the savvy sample of Lord Finesse’s “Hip 2 Da Game.” While the interpolation was seen as an affront by the Bronx great, the choice in and of itself was a signal of how close Mac had his ears to the genre’s roots. And it’s not just the quality of the source material that’s allowed “Kool Aid & Frozen Pizza” to age better than much of Mac’s early work; his verses capture an evocative slice of those carefree summer days of high school, when you feel you actually could be the greatest alive, but also expect to be perennially underrated. It’s a song enthralled in being on the cusp, when the thrill of the ride feels like the ultimate destination itself.

While Mac’s critical breakthrough Watching Movies With The Sound Turned Off is typically cited as the turning point in his career, his post-frat second act really began on the previous year’s Macadelic. Coming off widespread mixed reviews, including a notorious 1.0 from Pitchfork, for what was supposed to be the coronation of his young career, Mac could easily have become bitter, doubling down on the sound that gave him his runaway success as a “fuck you” to naysayers. Pop stars have turned villainous over higher scores. Instead of lashing out, Mac considered the negative reception as something worth reckoning with.

The resulting mixtape saw Malcolm opening up his world beyond the confines of his suburban upbringing, courting validation from underground stars like Joey Bada$$ and established elders like Lil Wayne and Cam’ron. His outlook expanded and became more inquisitive, with hooks from the projects including “What the fuck is time?,” “What am I doing here?,” and “What if it’s gone tomorrow?” While his raps gained greater depth, the songs never grew too serious in turn. “Fight The Feeling” is the project’s most enduring relic for how it embodies this balance. The song finds Miller interrogating himself more honestly than critics were likely to do at the time, yielding plainspoken but piercing bars like “I’m a Beatle to these young kids/ But sometimes I be feelin’ like a needle to these young kids.” Yet the music feels like a breeze, pairing percussive plinks and scribbling guitars with a warm hook from Iman Omari and a humble verse from a pre-messiah Kendrick Lamar, coalescing into the type of headphones anthem you could easily leave on repeat for an afternoon (well, if not for the jarring pornographic audio inexplicably stitched onto the end of the recording, a gag Mac would pull more than once).

Mac Miller dropped five projects in 2013, a hot streak that included a horrorcore mixtape credited to his Slim Shady-esque alter ego Delusional Thomas, a FlyLo-styled beat tape, and a formative Vince Staples EP. Following an inspired side venture dubbed as Larry Lovestein & The Velvet Revival and leading into his third act beginning on Faces, it makes up something of his most fertile and impressive period, when he was proficient within several styles all at once, seemingly boundless in what he was capable and willing to try. “Earth” may have felt like a slight experiment among his many when it first appeared as a Watching Movies B-side tacked onto his live album from that tour, but it’s easy to trace back as a significant prototype for where his sound would go, one of the many seeds Mac was planting during this time.

After an extended intro that conjures the image of Mac leaning on a microphone stand warming up a jazz lounge, he throws himself into a semi-spoken word poem that perfectly balances sweet nothings with charming horndog fervor. Future meets him halfway with a striking loverman verse of his own, back before the rapper’s post-Ciara hedonism swallowed his psyche. Arriving three years before the sultry yacht rap of The Divine Feminine, the song is everything that works about that album in miniature, channeling its sometimes contradictory themes into a more honest ode to the finer sex and the ways they get you “sober off of conversation.” But even without the foreshadowing, it stands on its own as a certified jam, one of the most endearing love songs by a rapper with the rare pen for them.

Mac’s third studio album GO:OD AM felt a little too much like a major-label effort, with out-of-step guests like Miguel and Little Dragon adding elements that crowded Mac’s sound out of the infectiously off-kilter production that ran through all of his releases spanning from Macadelic through Faces. As a writer, however, Mac was pushing himself into even more adventurous territory, taking the surrealist non-sequiturs that defined Faces and stringing them into fully-formed narratives of recovery, relapse, and the road between. As is the case with too many rappers from the last 10 years, Mac was drawing those themes out into spectacular art that resembled reality too closely for comfort, never more than with GO:OD AM centerpiece “Perfect Circle/God Speed.” The song is an eight-minute odyssey of Mac’s highs and lows, with a sobering beat switch ushered in by an actual voicemail from Malcolm’s brother tenderly reaching out to encourage him home.

It’s too easy to retroactively ascribe clues that eerily foreshadow any artist’s ultimate passing, but Mac was an especially unsettling case, penning almost verbatim what would mirror his last couple of months in the lyrics, “Everybody sayin’ I need rehab/ ‘Cause I’m speedin’ with a blindfold on/ It won’t be long until they watchin’ me crash/ And they don’t wanna see that/ They don’t want me to OD and have to talk to my mother/ Tell her they coulda done more to help me.” As hard as the song can be to listen to today, it exemplifies the defining quality of Mac’s writing: his bravery, displayed in his unflinching gaze into the darkness of his own existence. He wasn’t afraid to “Admit it’s a problem, I need to wake up/ Before one mornin’ I don’t wake up.” And he was actively fighting too, recording as a way to will his way out in real time.

Mac was a team player, one of rap’s finest. He never made friends for favors, but they often unlocked some of his best work, and he in turn made sure to give back any chance he could, turning his albums into rich family affairs with recurring guests like ScHoolboy Q, Ab-Soul, and Vince Staples. Even posthumously, his spirit served as the muse for some of his regular collaborators most stunning singles, from Thundercat’s “Fair Chance” to Anderson Paak’s “Cheers.” Yet both on the mic and behind the boards, his chemistry was never stronger than it was with Earl Sweatshirt. The precocious pair pushed one another to some of their greatest recorded moments, from the bar buffet over the all-timer Earl beat that is “New Faces Pt. 2” to the dark spirits they conjured on the frantic, possessed “I’m Not Real”.

But it’s the original demo of Mac’s Watching Movies opener “The Star Room” that stands as their most spectacular achievement together. The version of Earl’s instrumental that ultimately served as the album’s intro is its own hazy splendor of producer magic tricks, introducing a more dizzying Mac than anyone catching up from Blue Slide Park could have foreseen. But the uncleared version intended for the album better serves the lyrics, dropping the Delusional Thomas verses and emphasizing the weight of Mac’s throat-clearing introspection: “I still don’t got the heart to pick my phone up when my dad calls/ Will he recognize his son when he hears my voice?” The combination of the weightless melodies – including a stunning Moonrise Kingdom sample — and Mac’s coming-of-age stoner wistfulness conjures the feeling of a Studio Ghibli movie starring Snoop Dogg. The result is an acid-tinged lullaby from two kindred spirits who never shied away from making their most transgressive work also their prettiest.

Swimming is not an uncommon songwriting metaphor to describe the desire for progress. Scott Hutchinson of Frightened Rabbit saw it as a means of moving beyond the past, advising to “swim until you can’t see land.” Julien Baker would later sing of swimming as an act of desperation, bemoaning that “the harder I swim, the faster I sink.” Mac’s take, however, was less focused on escapism. He saw swimming – the bristling up against the fluid friction of life – as the end goal; to never find land but never need the shore anyway. “Come Back To Earth,” the stunning album opener to Swimming, begins as a regretful confessional, a plea to “do anything for a way out of my head.” But then, with a guitar flourish, the song exhales, and Mac harmonizes with himself, “I was drowning, but now I’m swimming/ Through stressful waters to relief.”

“Come Back to Earth” is a gentle, percussion-less ballad, stylistically out of step with the “sophistafunk” and chamber jazz of the rest of Swimming. Yet the song set the template for what would become Mac’s final transformation on his next and last album Circles: the soul-searching soul singer. It’s also the perfect encapsulation of the tension at the heart of his resonance as a writer, how he never believed in some vague notion of happiness as the resolution to his struggles, but rather his capacity to float on in balance. “Come Back to Earth” is a short song, more of a prayer really. With it, Mac perfectly captured the waxing and waning of depressive episodes, and all the little daily epiphanies that keep one’s head over the oncoming waves.

Mac’s early work was informed by his youthful exuberance, the typical trappings of unripe bravado that feels like you have the world already figured out before you spend the rest of your life trying to catch back up. But Mac grew up remarkably fast in the public eye, quickly phasing out of his reputation as “Easy Mac with the cheesy raps.” Sitting within the fantastical mess of Watching Movies was “REMember,” a raw and pained account of the shock, bargaining, and resulting promises that accompany one’s first experiences with grief. The song was dedicated to Reuben Eli Mitrani, his late childhood friend whose initials are memorialized in the song’s capitalized letters, and whom Mac lovingly described in fine strokes as “part-lion.”

“REMember” simultaneously serves as Mac’s broader plea for idyllic days lost to time, before his real life became intractable with the challenges of the real world. The song takes a special resonance in Mac’s absence, as the artist himself became the subject of similar eulogies mourning those lost too soon. For Mac’s fans who grew up with him, “REMember” is an ode to their relationship today: all memories, longing, gratitude, and the desire to recover any part of you from a past that’s unthinkably out of reach.

To Mac, death seemed inevitable. He spoke of his demise throughout his discography, in casual tones as though it was expected, a reality awaiting a few pages away. His music is littered with little sucker punches for fans still grieving from his passing, the way he tosses off tragic predictions of how he’d meet his end in between irreverent punchlines. Those allusions scattered across Faces — from the frank opening declaration, “Shoulda died already” to the more abstract “I’m gettin’ faded ‘til the angels comin’” — give the album its eerie hallucinogenic twinge. His grandest treatise on his own death is aptly titled “Funeral,” placed in the dead center of his most afterlife-inspired album.

“Funeral” embodies much of what makes many fans see Faces as Miller’s definitive statement: It’s a patchwork of instant quotables that mix delirium with poignant self-reflection and simply keeps it moving, touching in its runtime Mac’s desire to never orphan a child, the unsustainable pace of his life, and the parting wisdom to always “party like it’s the last day of your life.” How many ideas he crammed into just this one song — as well as the rest of the 24-track album — is a reflection of just how generative this period of Mac’s life was, when he built his own studio hideout and would have to be dragged out to meet other obligations. That obsession also reflects how deeply intractable he was with his addiction in this period, something he channeled movingly into this self-eulogy: “Doin’ drugs is just a war with boredom but they sure to get me…A shame my tragedy my masterpiece.”

Circles was an indication of what a fully post-rap Mac might have sounded, shepherded by the sage wisdom and mutual admiration of Jon Brion. In an >interview about the album, Brion described how Mac’s musicianship could move him to tears. While Mac would insist the producer record the instrumentation for him, Brion found subversive strategies to convince Mac to play what would end up on the record. Brion rightfully heard something uniquely expressive in Mac’s performances — how his songs could come to him fully formed by simply playing his thoughts out loud. “Woods” feels driven entirely by that instinct.

The soft ripple of “Woods” is the midpoint of Brion’s work on Late Registration and the Eternal Sunshine Of The Spotless Mind score. The throbbing synth line captures the sensation of being stuck inside your head that Mac details on “Come Back to Earth.” He uses the platform to search for meaning in his endless oscillations through love and heartbreak, addiction and recovery, failure and redemption. “It’s so much better when you wait/ Forever and a day, that’s all I got,” he pleads, rationalizing the trials of the journey he’s been on before he loses once more either another lover or himself. “Woods” is a direct window into the ache of Mac’s longing to keep going on, and as one of the final songs he worked on before passing, what all we lost from his being prevented from doing so.

In the hours after Mac’s passing made the rounds on social media, his performance on NPR’s Tiny Desk – uploaded one month prior – quickly resurfaced as the Internet’s chosen shared obituary, passed around as the definitive piece of lore that defined his essence without the need for further words, like DMX at Woodstock ‘99. If you find yourself still left wondering why Mac was considered so special after all the exposition above, let his Tiny Desk Concert be the final argument you hear out. Beyond his affable, unpretentious demeanor — the wunderkind who looked at everything with wonder — the ineffable quality of his flow is nearly tangible within this performance of “2009,” Swimming’s penultimate track but spiritual closer, and the greatest song Mac ever put to tape. The rendition is equally heartbreaking and inspiring to watch today, Mac delivering with an uncontrollable physically his hard-earned reflections on a career and life that ultimately taught him to value what he owed himself above anything he might be owed.

“I don’t need to lie no more/ Nowadays all I do is shine, take a breath and ease my mind,” he boasts almost as if confiding, taking stock of and ultimately pride in the peace of never being perfect, instead living by your accumulated lessons and trusting the process. The questions in which he turned his career over to remain unsolved, but also set aside. Mac spent a lot of his music predicting various futures he was heading towards as he tried to outrun his demons, but on Swimming you heard the sound of an artist who was learning to stop moving and find resolve in the present. You have to believe that as he traced both the disillusionment and awe of what laid beyond the start of his career, he truly felt satisfied in the measure of the distance he covered both inside and out. “A life ain’t a life until you live it,” he claimed emphatically. In that regard, Mac lived more than most, enough to lend some of that life onto the rest of us.