Here it is: the pivot point in Kanye West’s career and maybe recent hip-hop history at large.

If you’ve followed the development of rap music over the past decade, you’ve undoubtedly heard the influence of 808s & Heartbreak, the album Kanye released 10 years ago this Saturday. And if you’ve followed critical discussions about rap during that time period, you’ve probably noticed the prevailing theory that 808s changed everything. Dissenters occasionally push back against that narrative, dismissing it as a byproduct of Kanye’s self-mythology, but they’re fighting a losing battle. We can debate in circles about how original 808s really was and whether it’s a work of genius, but there’s really no argument against its status as one of the most important albums in music history. As the years roll on, it only looms larger over the landscape of rap, R&B, and the whole of mainstream pop.

One thing 808s & Heartbreak did not do was popularize Auto-Tune. The pitch-correcting software, which makes humans sound like highly emotive machines, was all the rage in the late aughts, largely thanks to T-Pain. The Floridian made waves with 2005 debut Rappa Turnt Sanga, but his 2007 chart-topper Epiphany and an endless stream of high-profile guest spots (among them R. Kelly’s “I’m A Flirt,” Flo Rida’s “Low,” DJ Khaled’s “I’m So Hood,” Lil Wayne’s “Got Money,” Chris Brown’s “Kiss Kiss,” Plies’ “Shawty,” Jamie Foxx’s “Blame It,” and Kanye’s own “Good Life”) were what ensured Auto-Tune became an inescapable aesthetic.

It was one of those polarizing forces that sometimes sweep through music. Artists either took a stand against Auto-Tune, decrying it as a crutch for people who can’t sing, or they began to dabble in it themselves — sometimes because they did need a crutch, but also sometimes because they recognized it was just another sound effect opening up new creative possibilities, no different than the distortion pedal.

One of those dabblers was Kanye West. Kanye is no one’s idea of a great singer, and Auto-Tune certainly emboldened him to attempt ideas he would have otherwise delegated to more gifted vocalists, but his headfirst dive into Auto-Tune in 2008 had more to do with creative expression. He clearly saw vast potential in the effect beyond T-Pain’s sex-robot routine — “I could never be your robot,” he later rapped on 808s highlight “RoboCop,” a notion no one ever doubted, at least until his recent Manchurian Kan-didate behavior in support of Donald Trump. Rather than a trendy sound effect, Kanye saw in Auto-Tune the power to communicate detachment and despair. We got a preview of this potential the first time Kanye rapped through Auto-Tune on a record, his guest verse on Young Jeezy’s “Put On” in May of 2008.

A lot had changed for Kanye in the months since Graduation. Career-wise things were better than ever: He’d vanquished 50 Cent in their much-hyped sales battle, gone to #1 for a third time with “Stronger,” and piled up rave reviews for his ambitious Glow In The Dark Tour. He’d established himself as, if not the biggest rapper in the world, at least a serious contender for the throne. (Remember, this was the same year Lil Wayne’s virtuoso mixtape run climaxed with the blockbuster Tha Carter III.) Yet he’d never felt lower or more alone. His engagement to fashion designer Alexis Phifer had ended less than amicably, just months after his mother, Donda West, died due to complications from cosmetic surgery, a fate Kanye still blames himself for. At the peak of his popularity, he was miserable.

Although the album mainly focuses on the breakup, the death of Kanye’s mom was arguably the main catalyst for the transformation that began with 808s & Heartbreak. In hindsight, it was the beginning of a dark night of the soul that still hasn’t really ended a decade later. At least, it sure seems that way from afar, as an observer of his public behavior and recorded works. Again and again he’s returned to the subject, approaching it from different angles, dreaming of her presence, haunted by her absence. He developed a video game that imagines her as an angel flying through the heavens. He’s never been the same since.

“Put On” may or may not be the first song Kanye recorded after Donda died, but it’s the first time he addressed her death on a song. Before Kanye’s appearance nearly three minutes in, “Put On” is peak Jeezy: a grandiose monster-truck of a song, gothic and street regal. And all of the sudden, tacked onto the end of this titanic Jeezy single about repping for your city, comes Kanye West mewling in pain through a vocoder, casting an ominous pall over Drumma Boy’s production. Amidst complaints about betrayal and isolation and the perils of fame, he laments, “I lost the only girl in the world that knew me best.” It’s harrowing. Writing in the Village Voice 10 years ago — under the prescient headline “Kanye West: Going Nuts?” — my colleague Tom Breihan described it like so:

Throughout his verse, Kanye abruptly switches between wounded openness (“All these Jesus pieces can’t bring me peace”) to ugly if standard-issue rap girl-talk (“Sure I need just at least one of Russell’s nieces”) and back again. And with the benefit of that robot-filter, he stretches his voice into shapes he’s never attempted before, dramatizing his emptiness. For reasons I can’t quite place, it just kills me when he sings, “I’m so lonely,” stretching that I into a long moan. It’s a verse about losing the people who really matter to you and who understand you, about being surrounded by people who want something from you instead, about the paranoia and bad faith that come along as byproducts of wild success. That it comes stapled onto the end of a triumphal Jeezy single somehow only increases its impact. It’s the saddest thing I’ve heard in forever.

There was plenty more sadness where that came from. Arriving six months after “Put On,” 808s pushed Kanye even further into darkness, altering his signature sound in ways that perplexed the watching world and instantly rewrote his career arc. With a braintrust including No I.D. (his mentor), Jeff Bhasker (who’d later help My Beautiful Dark Twisted Fantasy sound so humongous), and Kid Cudi (the latest signing to his G.O.O.D. Music label), Kanye holed up in Hawaii for three weeks and came away with the coldest album of his career. Instead of rapping, he mostly sang through Auto-Tune. Abandoning the colorful hip-hop production he made his name on, the album was a frigid wasteland of brooding synth-pop. And in place of the volatile but mostly buoyant egotist who’d successfully remade rap in his own image, we were now privy to the nastiest impulses of an embittered soul. It was a near-total reinvention of Kanye West.

This metamorphosis gave us some of the most incredible musical flourishes in a career full of them. Opening number “Say You Will” paired wound-licking digital howls with stark blips, mournful synth pads, and booming low end for three minutes, then let the beat carry on in quiet desperation for another three. “Welcome To Heartbreak” carved Kanye’s personal distress into a stunning sonic ice sculpture: “Chased the good life my whole life long/ Look back on my life and my life gone/ Where did I go wrong?” The album brightened up briefly in the middle with “Paranoid” and “RoboCop,” two lushly symphonic new wave tracks that masked scathing sentiment in immaculate production. It got very dark again very quickly with “Street Lights,” arguably the most powerful song on the album, which shrouded Kanye in weeping keyboards and layers of shimmering static, as if beamed from the bottom of a frozen pond. “Life’s just not fair,” he muttered, sounding like an android whose hardware is about to give out.

This was astoundingly beautiful music, but people didn’t know what to make of it at first. Some protested Kanye’s use of Auto-Tune on purist grounds. Others rejected some of the more minimal productions as unfinished sketches. Even in the far less self-consciously woke environs of 2008, Kanye faced blowback for his misogynist disposition. Many noted that he was lashing out against a woman who had no platform to respond to being dubbed a “spoiled little LA girl” and accosted, “How could you be so Dr. Evil?” (possibly the clunkiest lyric in a career riddled with bricks).

Aside from the now-quaint opposition to Auto-Tune, the early critiques weren’t wrong, but none of them really stuck. Kanye continued to shame and browbeat his exes on record for years later, and much of the public (myself included) never held him accountable for it, at least until his recent MAGA heel turn cost him his golden-child status. (We as a society scolded Kanye far more harshly for stage-crashing Taylor Swift the following summer than for anything he’s ever said on a record.) On a lighter note, although songs like “Heartless,” “Amazing,” and “Love Lockdown” could easily have been demos, it didn’t stop them from becoming massive hits. “Heartless” in particular now elicits some of the most enthusiastic reactions at Kanye’s shows. The initial confusion eventually gave way to acceptance and, ultimately, love for this new iteration of Kanye.

Crucial to the makeover was Kid Cudi, a young Cleveland native who lent his pioneering vision to 808s. A few months before 808s came out, Cudi had released his breakthrough A Kid Named Cudi mixtape, a collection that marked him as a truly original force in music and got him signed to Kanye’s label. Revisiting that project for Stereogum recently, Pranav Trewn called Cudi “something of the God particle for contemporary hip-hop” and identified him as Kanye’s muse for “the most game-shaking period of his career, one that would go on to submerge the rest of rap music in a wave of soft palate pathos.” It’s true; Cudi’s influence hangs heavy over 808s, an album that in turn transmitted his depressive posture, omnivorous taste, and line-blurring vocal approach to a far wider audience. Cudi lends his mushy, peach-fuzzed voice to one track, “Welcome To Heartbreak,” and he’s credited as a writer on three others, but his presence on 808s can’t be understated. His spirit hovers over the surface of the album almost as profoundly as Donda’s.

Auto-Tune helped Kanye convey his feelings of desolation, but it also liberated him to do things with his voice that Cudi was willing to try without the software. With his original trilogy of The College Dropout, Late Registration, and Graduation, Kanye had proved that a guy who came up as a producer could make it as a rap superstar, and he’d helped to collapse the binary between mainstream and underground rap — “first rapper with a Benz and backpack” and all that. With 808s, he suggested that rappers could be singers, too, regardless of whether they could sing. It started a revolution that at this point has swallowed up most of the influence of his first three albums — which, at the time of 808s & Heartbreak’s release, would have seemed insane given the number of rappers who by then were ripping off “the old Kanye.”

Now, neither Kanye nor Cudi was the first rapper to break into an awkward croon. Think of Biz Markie on “Just A Friend,” of André 3000 on countless Outkast songs, of Lil Wayne on “Lollipop,” the song that ruled summer 2008. Yet in the hip-hop mainstream there was a clear, longstanding distinction between rappers and singers; you picked one lane and stuck to it. 808s obliterated that boundary. In doing so, it set a new template that eventually became the new template. Less than half a year later Drake released his star-making So Far Gone mixtape, on which he never bothered to choose between rapping and singing. The lovestruck “Best I Ever Had” was the tonal opposite of 808s, but the connection was clear enough to get Drake dubbed “a post-808s & Heartbreak artist” in a Pitchfork review (Tom Breihan once again, ladies and gentlemen).

Drake wouldn’t be the last to turn to 808s as a sacred text. It’s easy to hear the album’s legacy in Future’s croaking robotic nihilism, in Travis Scott’s depressive widescreen goth-rap, in Post Malone’s genre-flouting blue-eyed trap, in self-appointed rock star Lil Uzi Vert and an entire legion of SoundCloud rappers. It might as well be oxygen in the modern rap mainstream. Any trap star who communicates in zoned-out electronic moans owes something to this album, as do many polyglots who treat singing and rapping as a sliding spectrum. Unfortunately, 808s continues to wield a heavy temperamental influence as well, both in the hopelessness that has become pop’s morose new normal and more specifically in the toxic breakup ballads of artists like Juice WRLD. Kanye didn’t invent being a dick to women on record, either, but we shouldn’t gloss over that part of his influence.

The extent to which the ethos of 808s & Heartbreak has infiltrated mainstream rap reminds me of the impact Nirvana’s Nevermind still claimed on rock in the late ’90s and early aughts, as grunge became post-grunge became butt-rock. The further you got from the original source, the more the sound mutated — sometimes for better, often for worse — but the lineage remained obvious long after the inspiration had curdled. At a certain point all the garbage it influenced began to somehow degrade Nevermind’s legacy. It took the onset of many other trends (nu-metal, Radiohead wannabes, the post-Strokes “return of rock” movement, and O.C. festival indie to name a few) to properly relegate the Nirvana sound to a historical relic.

Kanye himself has pivoted many more times since 808s: to the IMAX prog-rap of My Beautiful Dark Twisted Fantasy, to the transgressive noise-rap of Yeezus, to the jubilant gospel-rap of The Life Of Pablo, to whatever Ye was supposed to be. Each of those albums has made its mark, but in terms of setting the agenda for the sound of hip-hop’s mainstream, 808s continues to overshadow them all. We’ll probably need another 10 years to hear it with fresh ears again, once rap has experienced a few more tectonic shifts and this blast from the past no longer sounds so much like the present.