Emotions are not for the faint of heart. We live in a world that pushes eternal positivity and shames those who sometimes feel otherwise. Yet we can not enjoy the euphoria of new experiences, the passion of artistic interests, or the peace of exploring spiritual pursuits, without bracing for the negative emotions that exist on the other side of the psychological coin. We are all susceptible to this darkness — the anxiety that blindsides us and suffocates our mind, the depression that soaks the color out and turns off all the lights around us, the heartbreak that plunges us underwater, or the existential dread that leaves us questioning both our self-worth and the meaning of humanity’s existence. Attempting to grapple with and navigate this emotional landmine can be near-impossible. Without a roadmap, we are left trying to light our way through the fog — disoriented, scared, and isolated.

For many who struggle endlessly through these troubling times, hip-hop has provided that roadmap. This art form has birthed a spiritual home for countless people to re-discover hope and joy. When it feels like we are the only ones trying to crawl our way out of the dark chasms that engulf us, these songs provide a profound sense of understanding for the emotions that are too terrifying to verbalize. As artists approach the mic with the conscious decision to be vulnerable and share the complexity of their suffering, their music can save the lives of those who listen to it while permanently shifting the direction of hip-hop itself. As these personal and musical risks are taken, hip-hop dives deeper into new waters of emotion introspection.

Hip-hop has always provided a voice to the voiceless and storytelling for neglected stories, but providing emotional introspection for the emotional has been a longer journey. This journey towards emotionally introspective hip-hop has not been a gradual and linear progression, but instead has crash-landed as a set of three earth-shattering waves over the last 30 years. Each wave coincided with the coming of age of a generation, bringing with it a revolutionary new landscape of emotional introspection in hip-hop that shifted the lives of individuals and impacted the culture forever. In the last couple years, hip-hop’s third wave has taken the world by storm, led in large part by Tyler, The Creator and Brockhampton.

But to understand how these artists led this current wave, we need to understand the waves that came before.

“When I die, f*** it, I wanna go to hell / ’Cause I’m a piece of s***, it ain’t hard to f***in’ tell” — The Notorious B.I.G. (“Suicidal Thoughts”)

“Suicidal Thoughts” by The Notorious B.I.G.

Cue the early to mid 90s. The first wave emerged in full force as The Notorious B.I.G. revealed his all-consuming self-hate on 1994’s Ready To Die (“Suicidal Thoughts”), Tupac poured out paranoia of his possible murder on 1995’s Me Against The World (“If I Die 2Nite”), and Jay-Z lamented his drug-dealing past on 1996’s Reasonable Doubt (“Regrets”). These myriad of issues — self-hatred and shame, paranoia and fear, guilt and remorse — all led to suicidal tendencies that these artists depicted with visceral detail. To hear these larger-than-life rappers, who burst with swagger and confidence, step down from their society-bestowed pedestals and expose their darkest thoughts with full honesty was unbelievably inspiring.

Yet while the lyrics seeped groundbreaking depths of vulnerability, the production and vocal delivery showed hesitancy to approach the same levels of sensitivity. “If I Die 2Nite”, with its pulsing bassline, aggressive drum beat, and funk-influenced synth loops, along with Tupac’s larger-than-life hostile vocal delivery, maintains a level of vitriol expected in hip-hop. “Suicidal Thoughts” utilizes sparse piano keys, a muted drum beat, and Puff Daddy’s disregarded ad-libs to create a coldness that mirrors Notorious B.I.G.’s detached vocal delivery. “Regrets” employs a groovy bassline and a silky and jazz-tinged backing instrumentation that allows Jay-Z’s smooth, laid-back, and confident delivery to stay intact. All three songs have enthralling production that draws you into the bleeding mindset of these artists but also puts up psychological walls to maintain a sense of guarded authority.

The most striking aspect of these songs is that the emotions displayed often had to be devastating to be given hip-hop’s blessing. It begs the question: why did the collateral damage need to be death for these artists to have permission to show their emotions?

This question would linger in the hearts of many hip-hop fans and artists for more than a decade until another wave of artists decided to step further into the feelings that encompassed the human experience.

“Dad cracked a joke, all the kids laughed / But I couldn’t hear him all the way in first class / Chased the good life my whole life long / Look back on my life and my life gone / Where did I go wrong?” — Kanye West (“Welcome To Heartbreak”)

“Welcome To Heartbreak” by Kanye West

Cue the late 2000s to early 2010s. The second wave came without warning as Kanye West wrestled with the emptiness of fame on 2008’s 808s and Heartbreak (“Welcome to Heartbreak”), Kid Cudi shared the horrors of his depression on 2009’s Man on The Moon (“Soundtrack 2 My Life”), and Drake painted an intimate picture of heartbreak on 2011’s Take Care (“Marvin’s Room”). Suddenly, issues like disillusionment with success, mental illness, and romantic heartbreak were given full artistic license in hip-hop. To hear these artists embrace genuine sadness in a genre known for hyper-confidence was in it of itself a courageous and bold push forward for the art form.

In contrast to the previous wave, the production and vocals of this wave began to experiment with multiple genres and overall display an unprecedented tenderness for hip-hop. On “Welcome To Heartbreak”, the brooding synths and despondent piano chord progression emphasize the sorrow in Kanye’s auto-tune drenched singing. On “Soundtrack 2 My Life”, the electronic-tinged synths, distorted vocals, and psychedelic-influenced backing instrumentation help Kid Cudi’s raps to thrive in environments hip-hop audiences had not yet witnessed. On “Marvin’s Room”, the soft-spoken singing and atmospheric production allow Drake to veer into full-on RnB territory, save for a short rap verse and outro. All three of these songs expanded past traditional hip-hop sensibilities, embracing other genres to evoke a wider range of emotions for the listener.

This wave made groundbreaking strides towards greater vulnerability in hip-hop. These artists could now present a wider range of feelings without shame. Yet it is worth noting that the emotions presented in these songs were still grounded in specific instances of pain — concrete and unambiguous examples of disillusionment, depression, or romantic woes.

It would take yet another decade before the next wave of artists broke open hip-hop into uncharted territory: existentialism and the search for meaning.

“Boredom, boredom, boredom, boredom / Boredom, boredom, boredom, boredom /…I’ve been in this f***in’ room so long / My eyeballs are turning to drywall / My friends suck, f*** ’em, I’m over ’em / “Hi y’all, y’all ain’t hit me all day / What the f*** is the problem? Is it me? / ’Cause I’m not solved, I’m… bored.”

“Boredom” by Tyler, The Creator

Cue 2017 and onward. The third and current wave blossomed as Tyler, The Creator struggled with existential questions of boredom, loneliness, identity, and nostalgia on 2017’s Flower Boy (“Boredom”, “911 / Mr. Lonely”, “Garden Shed”, “November”) and Brockhampton longed for self-love, friendship, and authentic self-image on 2017’s Saturation trilogy (“MILK”, “LAMB”, “RENTAL”). By releasing all their emotions that veered into the abstract and ephemeral, these artists took hip-hop in an unexplored direction by bringing existentialism to the forefront of their music.

These songs took even larger artistic risks than the previous wave. Tyler, the Creator and Brockhampton blended hip-hop with neo-soul, industrial music, alternative rock, and even indie pop, a genre often seen as antithetical to hip-hop. With this range of genres, they intertwined existentialism into the fabric of the instrumentation and vocals — creating a disarming fusion between beautiful, multi-layered production and sobering vocal delivery. This alarming dichotomy is present on “Boredom”, as its lush piano keys, melancholy guitar chord progression, and soft gospel-tinged crooning build a heavenly backdrop for Tyler’s angsty and downtrodden philosophical questions. Similarly, “RENTAL” contrasts buttery piano chords and warm synths with scratchy sound injections and pitch-distorted vocals to create a surreal environment for Brockhampton’s desires of peace and self-satisfaction.

It was shockingly beautiful to hear these artists not just expose their feelings, as the previous waves had done, but also ask thought-provoking questions about identity, existence, and self-love. These questions stripped back the front we put on to the world, revealing our most naked insecurity: our relationship with ourselves and the existential dread that comes with it.

Coming into the world shortly after the first wave of introspective hip-hop, growing into teenage years during the second wave, and arriving into adulthood during the third wave, I feel grateful to have been able to grow alongside hip-hop. When I listened to these songs, the problems that often made me feel too sensitive or scared suddenly became worthy of validation, of discussion, and of artistic beauty.

As hip-hop has evolved, I and so many others have evolved with it. It is no coincidence that a significant portion of each generation grew into adulthood with the timing of each wave — Generation X for the first, Generation Y for the second, and Generation Z for the third. With each wave, we give ourselves permission to become more introspective, more vulnerable, and more emotionally healthy as we are pushed further to the shores of understanding the great depth and complexity of the human condition. The more we are pushed onto these shores, the more we can be understood. The more we can heal. The more we can grow.

As I stumble onto these shores of real adulthood, I brace myself for the bewildering and life-affirming emotions that are bound to come my way. Before I venture out into the unknown, I take a long look back on those waters. For a moment, I feel lost and overwhelmed. But then I remember something.

I know what songs to play.