Looking back, it’s apparent that 2008 was a significant turning point for hip hop. Physical media and the old ways of discovering artists were gradually being phased out by an interconnected network of blogs and social media sites like MySpace and YouTube. The business of rap music was rapidly evolving in accordance with the times, as a new crop of “viral” artists began building dedicated followings by releasing free mixtapes online.

None would go on to be more influential than Kid Cudi, a Cleveland native who went from being an underdog with zero career prospects to having Roc-A-Fella’s college dropout on speed dial. With Kanye’s cosign, Cudi became more than just the poster child of the blogwave era. He honed a unique and versatile toolkit that included multi-genre covers and a mix of rapping and crooning, all without pandering or showboating. His meditations on cannabis and explorations of self, described by Jeff Weiss as “sad robot rap,” were endearing, wildly original, and shied away from the one-dimensional hyperbole that characterized the music of many of his peers.

Cudi ultimately grew into his role as the principal curator of a moody subgenre of hip hop that has infiltrated and in many ways defined the scope of nearly everything that followed in the wake of his monstrous breakthrough. He helped carry the commercial viability of synthetic textures into contemporary hip hop, expanding upon Ye’s Graduationformula to carve his own EDM-inflected niche in the Earth’s stratosphere. He predicted and subsequently fostered many of the dominant musical trends of the past decade, and even penned four songs (including hit singles “Heartless” and “Paranoid”) for 808s & Heartbreak, widely considered to be one of the most important records of the 21st century.

While there’s no denying that Cudi’s impact on music and hip hop culture will continue to reverberate long after he decides to hang up his space suit, it is the honesty and openness of his musical approach that has resonated the most with audiences. Sappy tropes aside, Cudi’s music has proven to be both immensely therapeutic and empowering for many feeling lost and out of touch in a digital world fraught with ample reasons for despair. He is the unlikely hero who is easy to root for because many people see in him what they see in themselves. The loneliness, depression, and anxiety stemming from withered relationships and the unforgiving nature of humanity is so much more than just contrived subject matter used to drum up platinum plaques; it represents a very real bond connecting Cudi to listeners. He has never professed to having a cure-all for conquering demons, but instead counsels that rebirth is indeed possible, offering forth a lifeline for those who feel as if they have no one to turn to at their lowest. His music is familial, his message universal. In the heart-wrenching Facebook note announcing that he was checking himself into rehab for suicidal urges, Cudi reiterated that it was a daily battle, but one that can be won: “I deserve to have peace. I deserve to be happy and smiling. Why not me?”

For all the cliches that get tacked on to being labeled a once-in-a-lifetime talent or the artist who “single-handedly changed my life,” the self-proclaimed outcast unequivocally belongs on the Mount Rushmore of this generation, right alongside the likes of Chief Keef, Drake, Future, Kanye West, Lil Wayne, and Kendrick Lamar. Because when Scott Mescudi said that he was our “big brother,” he meant it in a way beyond the immediate association that comes with kinship.

Disclaimer: this list encompasses Cudi’s solo discography and songs where he appears as the main act. As such, it does not include songs where he is a featured artist.

Cudi’s unapologetic vulnerability and individualism are an essential part of his musical signature. Although he tends to wield his creativity through experimental melodies, he occasionally unleashes a torrent of straight-raps to get his point across. That’s exactly what he does on “Too Bad I Have to Destroy You Now,” a song whose grandiosity sounds like it was lifted straight from the Hayden Planetarium. It’s an intergalactic sonata that pulsates with energy as Cudi the fatalist waxes about his destiny. The naysayers may continue to doubt him both openly and behind his back, but the truth always comes to light, and Cudi is slowly gaining confidence in his purpose among the stars.

On an album that spends a great deal of time dissecting the black hole that is depression, “Immortal” sees Cudi recapturing his Lion Heart. The tribulations that dogged his past have suddenly sent “lightning” coursing through his veins, a supernatural shift that seems to herald his return from the depths. This creative spark is evident in the song’s structure: a screaming Billy Madison revels in the moment of empowerment, grabbing the listener’s attention as a reversed sample of MGMT’s “Congratulations” purrs into place.

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Before Drake was linking with Swedish indie poppers on 2009’s So Far Gone EP or Kanye was painting pictures of heartache with 808s, Cudi was ushering in the digital age with a seamless blend of rap, indie rock, electronica, and dubstep. On “Embrace the Martian,” he dipped into the underground electronic scene and came up huge in recruiting one of the internet’s favorite house production teams. Even amidst the hubbub of Crookers’ frenetic instrumentation, Cudi is remarkably self-aware: he just wants to be accepted and recognized as real. He’s no “Cloverfield” villain, but he has every intention of altering the landscape of a fickle music industry. “Embrace the Martian” is founded on a simple yet relatable concept that is executed to a tee, and is representative of the transitive state of hip hop in the late 2000s.

Cudi’s eternal faith in the choices that he’s made is the central theme of “By Design.” Fully submerged in the go-with-the-flow mentality, Cudi stands by his decisions, understanding that while hindsight may be 20/20, he’s fortunate to have made the most of the opportunities that presented themselves. It’s a basic if immersive philosophy that spearheads much of Passion, Pain & Demon Slayin’: rather than steering negative or wallowing in his destructive tendencies, he basks in the warmth of his own “frequency.” Pharrell and Cudi’s career-launching accomplice Plain Pat lend mint sonics to the song’s headliner and featured guest artist Andre 3000, who delivers an enlivened chorus.

This ethereal cruise through “The Land” rightfully deserves to be the introductory track at every Browns and Cavaliers game from here on out. Cudi’s picture perfect ode to the city that gifted him his “cool” is filled with a loopy love and admiration for the “double-O.” It’s not difficult to imagine Cudi “freakin’ Black & Milds” in his Cutlass Supreme while turning lanes in his hometown. Consider this Cudi’s version of “This Is Why I’m Hot.”

Opening with the same line that Andre 3000 used on the original song “Chonkyfire,” Cudi takes a deep dive into the morass of whatever substance will help him dull the pain. His ego percolates in the sensation of being “down and out,” warning the listener that they should think twice about wanting to enter his mind. A second verse reveals his intentions for telling this “no guts, no glory” story: the soulful guitar cuts out ever so briefly to allow Cudi breathing room to brood, as he contemplates the explicit nature of his life and the prospect of one day reuniting with his father at the gates of heaven.

Cudi’s steez is sky-high, and so is his flow. Mobbed by his fans (“I’m country to the seas”), “super duper Cudi” is looking and feeling the part: the candy-paint rag top, Bape gum bottoms, and thirty-day tag on the Jaguar are all part of the ensemble for Shaker Heights’ freshest emcee. With Chip Tha Ripper in tow, and stacks bursting from his 10.Deep pants pockets, Cudi is as nimble and clever as ever.

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It’s a full moon and Cudi’s transformation into a primordial “werewolf” of sorts has taken hold. Feeling emboldened by the carnal desires that the night brings, he prowls the streets looking for the woman who can “find the man within the beast” and help him change his ways. With only love and companionship to reverse the curse, the devilish spinning of Ratatat’s electronics fuel “the lone wolf” onward.

Cudder’s eccentricity and musical tastes know no bounds. Sampling Vampire Weekend’s “Ottoman,” he proceeds to blaze up the set with a “heap of good weed” to boot. Cudi remains unphased by the haters that want to see him come up short and the tabloids whipping up endless batches of speculation surrounding his personal life. Whilst in this sativa-addled state (“tap-dancing on a cloud”), Cudi can’t be restrained by earthly concerns. With the smoke to buoy his voyage, he’s going to continue putting it down for his fans.

This “wake and bake” is the curtain call of Cudi’s debut. He’s come to the conclusion that people are going to judge him no matter what, so he may as well shrug it off and look ahead to the promise of sailing into a new tomorrow like Peter Pan. Hope, compounded by a love for “higher learning,” is Cudi’s pixie dust for staying afloat, and he’s all in on living his life to the fullest. Common’s closing narration provides some rather foreboding hints that the second installment in the Man on the Moon series may not be as rose-tinted as the bookend of its predecessor.

With a strumming guitar lick to kick things into gear, Cudi and Kanye dive into a stadium rap-rock track that dramatizes a doomed relationship. The perils of the famous rapper stereotype (“I’m in the magazines, on the TV/No matter where you are, you might hear me”) offer plenty of source material for the two kindred spirits. Cudi bemoans the “new nightmare” of knowing that his feelings aren’t reciprocated, while Kanye elaborates with scatalogical puns on the “writer’s block” that he endured as a result of “Aria’s” antics.

Much like graphic-novel-turned-film Scott Pilgrim vs. The World, Cudi conceives of a tale that will take the viewer far beyond the horizon of his imagination and into some “‘generation next’ shit.” The ominous “other side” that Cee-Lo sings of on the hook contains instructions that are both enticing and profoundly off-putting. Once aboard the enchanted flight, there can be no going back: Cudi has welcomed the listener into a world where only the inevitable end holds any semblance of meaning.

“These motherfuckers can’t fathom the wizardry” is perhaps one of Cudi’s most iconic one-liners. “Mojo So Dope” invokes the essence of Austin Power’s sex drive to weave a song that reads like a case study on the scatter brain tendencies of its author. Cudi bounces around the confines of his skull, touching on everything from his position in the 2010 XXL Freshmanclass, the uncle that unknowingly contributed to his nephew’s early music career, to drowning his sorrows with Old English. The trauma is still as present as ever, but it’s augmented by nostalgia and the uncertainty of his future.

Listen good/I don’t have nobody” pinpoints the rhetoric that defines the horrors of things that go bump in the night. Haunting strings that serve as a backdrop to “Solo Dolo” almost seem to pluck away at Cudi’s sanity, as he travels deeper and deeper into the terrifying and existential unknown. It’s a riveting fever dream that trumpets the album’s aptly titled second act, Rise of the Night Terrors.

In the opening to this cloud-kissed symphony, Cudi is in sheer disbelief at having achieved such rarified air, as if he’s happened upon some forbidden plane of existence that must be too good to be true. A surprisingly uplifting record from the man known for his forays into fear and misery, the inexplicable soaring of “Cudi Zone” vividly captures a one-of-a-kind escape from the depravities of the mortal realm. Detractors and critics are forgotten, as Cudi drifts into a place where even the “Devil in a hot pink dress” can’t touch him.

If “Maui Wowie” was a joyful ode to the lengths that Cudi would go to achieve his next high, then “Marijuana” is a fully-formed realization of the side effects of the “pretty green bud” that wracks his mind. Cudi understands the dependency that is bred from always needing to be “stoned on the run-run,” but can’t seem to turn his back on the only thing that keeps him level. A spiraling piano loop mimics Cudi’s descent. As the track appropriately comes to a close at four minutes and twenty seconds, Cudi interjects with a timestamp that seems to foreshadow his eventual relapse into the madness.

“Just What I Am” is the first track that Cudi made for Indicud, an album that is frequently overlooked and doesn’t get the praise that it rightfully deserves. The project introduced Cudi the producer, a creator eager to shape the trajectory of his constellation-crossed journey while behind the boards. The song’s repetition of “I’m what you made God” feels like a continuation of Cudi’s constant struggle to convince himself that he is not some mistake from above, but rather a purposefully imperfect construction. The minute personal insights that shape Cudi’s denial and dismissal of professional help (“I had to ball for therapy, my shrink don’t think that helps at all”) are driven home in the poetic asphyxiation of the closing lines: “Whiskey bottles on the sinks and floors/Everyday to find sane’s a chore, amidst a dream with no exit doors.”

Built around the guitar riff from Kurt Cobain’s “Burn the Rain,” “Cudi Montage” details the feelings of suffocation that plague Cudi and the salvation that he prays for to ease the weight of the world on his shoulders. The song hits a nerve in a way that even “Reborn” and “Fire” fail to encapsulate; the cyclical nature of their respective past struggles has made both Cudi and Kanye reassess their life path in a way that neither could have predicted. Reinvigorated and rejuvenated by their newfound faith, and anchored by one of the best verses from Ye in years, it’s a fitting ending for an album that reaches for something more and hits all the right notes in the process.

The brilliance of Cudi’s music often lies in its stark simplicity, and “Mr. Rager” is no exception. Ensnared by addiction and wondering whether an overdose will finally bring an end to the fantasy (life), Cudi comes face-to-face with “Mr. Rager,” the warped persona pulling him ever closer to the grave. Cudi realizes that the outlet he’s chosen isn’t the gateway to happiness, yet his obsession with fulfilling the next high has blurred the lines beyond repair. Needing to put an end to his troubles, Cudi makes one last plea, knowing all too well the finality of his decisions. Made for those fed up with their lot in life, the track is pure, unadulterated escapism, its chorus designed to be a dialogue between the jarring forces within that pull in opposite directions.

There is a startling sense of security that comes from accepting the reason for one’s loneliness. This clarity is the very lifeforce of “All Along,” a cinematic closer from MotM II on which “the lionhearted” quietly concedes the battle and embraces the rejection that has tortured his soul: “What I need hates me…All along/I guess I’m meant to be alone.” It’s one of the most revealing and tragic tracks in Cudi’s entire discography.