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 Graduation formula 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.