All four of Kanye West’s solo albums since 2008 have elicited the same question: What’s wrong with this guy? We could figure it out when he released 808s and Heartbreak, as he was kind enough to put the answer in the title. Everything since has spurred reactions ranging from psychoanalysis to outright disdain.

We’re never going to get a single answer for what happened to Kanye. No one is so simple that their entire trajectory can hinge on a single discrete event—not even a mama’s boy whose mother died suddenly. Kanye is where he is because that’s how life works, and no Twitter rant or grandiose album will explain it concisely.

But why is this guy the one so many try so hard to understand? Anecdotally, it seems those who wish to make sense of him are equal in number to those who hate the contradictory mess he appears to be. Some search for his humanity while others complain about how hard it has become to find it in his work and persona. But few take the easiest, cheapest option: ignoring him.

Many are simply too invested to turn away, even if they hate what he has become. But how much of that is because they hate what they, themselves, have become? Is it about how Kanye has changed or how we’ve changed—or what’s stayed the same, even though we just knew things would be different?

One could argue Kanye West is the most unlikely superstar rap has ever seen. He’s not especially cool. He can be really good on the mic, but the safest description of him as an emcee is “serviceable.” He didn’t have a gangsta bone in his body, and the only way he could convince anyone he was a man who could change the game was by actually changing the game.

He wasn’t the first successful middle-class rapper—there have been plenty of those—but no one before him could sincerely relay his struggle to mainstream America and have such a broad swath of people truly relate to his perspective. Folks weren’t enjoying his music voyeuristically, as they had with so many hip-hop acts. Starting with The College Dropout, Kanye’s story hit so many hearts because it was so decidedly common at a time when going to college went from being a privilege to an expectation.

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Any semblance of hope in Kanye’s music is gone. The thing is, the same seems to apply to much of America.
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Like so many, he wanted to ditch those books and chase his dreams. Unlike most of us, he actually did it. And even though it took years to make it work, he came out on top. The College Dropout made him a sort of American hero. Our parents’ generation, the one that begged for the chance to go to college, was being replaced by one that wished it didn’t have to.

To root for Kanye was to root for self. I remember driving to campus while in grad school, struggling and running out of motivation, and playing The College Dropout every day on the way. The energy was infectious, and the stories were inspiring. The music was truly uplifting, even as I was the guy Kanye laughed at with all the interludes: broke, carrying around one advanced degree while working on another and lacking the courage to commit to what I truly wanted to do. I wasn’t going to walk away from school, but listening to Kanye made it sound like I could push to do anything.

Kanye was the vessel through which so many of us could live vicariously.

We wanted him to win because he’d made it clear how hard he worked for everything. The joy in his voice atop the soul of the samples—with a good-natured bravado that never obscured his vulnerability—made him seem as close to his audience as anyone ever had. He wasn’t just a rapper; for so many, he was their rapper. That made his victory lap on Late Registration, “We Major,” so triumphant. He’d really pulled it off. He was really happy about it. And without knowing him, so were millions.

That was 2004. Things are a lot different now. We met Kanye four years before the economy tanked. The kids who saw him on the campus tour supporting The College Dropout are now, in many cases, saddled with student loan debt and struggling to make it in cities with exploding rents. The life to which they thought they were entitled, the one where a degree was the beginning of a natural ascension, isn’t there for most.
Now it’s 2016, and most Kanye fans still wish they could achieve their dreams. Kanye’s achieved his, and yet he still sees himself as unsupported and underestimated. He sounds joyless, and many of those listening to him are having a hard time finding their own happiness. The Life of Pablo is more accessible and less furious than Yeezus and often as hedonistic as My Beautiful Dark Twisted Fantasy, but it’s never as warm, exciting or fun as his best work. The days of uplifting Kanye are long gone.

For six years, he’s been wrapped up in the best and worst of rich people’s Los Angeles—the fame that both enables and restricts, the superficial, disingenuous relationships and the kinky sex that keeps a lot of them going, the fantasies that seem so close, even though everyone knows real life has but one true exit. (LA is also the best guess for the thing that made Kanye “lose it,” especially considering how he cryptically blamed the city for his mother’s death.)

There’s nothing to cheer for in that. But is there anything to truly resent? This is what Kanye wanted and, in a roundabout way, what we wanted for him. Or maybe everyone just thought he was joking when he told us how dope he thought he was, or maybe it didn’t matter because it was hard to say he was wrong.

And this is who Kanye has always been. It’s not as though he has changed that much, but his circumstances certainly have. Getting what one has always wanted is a great way to discover there are even more things to yearn for. The wildly ambitious rarely stop when that plateau comes with a great view of things that look even better.

He was never one to stop. Kanye’s 38 now, but he’s the proto-millennial rapper. His music wasn’t just about how he felt, but about his feelings. The subtle distinction between those two notions—rather than simply telling us about his emotions, he’s always clamored for us to understand him. He defended his emotions rather than simply expressing them. And as the things he said became more outlandish, what was once endearing became indefensible.

His misogyny went from sounding childish to legitimately toxic—and that was well before he called Taylor Swift a ****. The ambition felt more like greed. Dreams seemed more like delusions.

He still yearns to be understood. It’s never been enough for Kanye to be Kanye. He’s always needed the affirmation of being told how great that is and how noble his intentions are in spite of his missteps. It came across as a desire for respect when he was just an underdog. Speaking from the top, it’s a call for exaltation, even if his message is fundamentally the same as it’s always been.

Any semblance of hope in Kanye’s music is gone. The thing is, the same seems to apply to much of America. If something’s wrong with Kanye now, it was wrong before, too. It’s just that none of us were in a position to notice.
Now that Kanye’s further from us than ever, the view is clearer. He’s the same guy he always was, but he’s harder to recognize with each passing day. He didn’t grow up in the ways he should, but he did in the ways no one hopes to. All the fame and fortune, but none of the fun.

Maybe making your dreams come true isn’t all it’s cracked up to be: Watching it happen to Kanye West has proven to be a letdown for everyone.

http://www.playboy.com/articles/why-do-we-care-so-much-about-whats-wrong-with-kanye