I recently watched the Oscar-nominated Amy Winehouse documentary. Having gone through college at the height of both Winehouse’s popularity and notoriety, the film was uncomfortable to watch.

Of course, in retrospect, the late-night monologues that mocked the incredible singer’s substance abuse issues and eating disorders feel incredibly tone-deaf and abusive in their own right. Shouldn’t we have known better? Well, we didn’t. But at that time, Winehouse was everyone’s favorite go-to punchline and mockery — track marks were just as important as the cat eye for any complete Amy Winehouse Halloween costume.

Even after Winehouse died in 2011, we didn’t take responsibility for how we — as a culture happily gobbling up every piece of gossipy tabloid trash tossed into our mouths — all but certainly contributed to this young woman’s demise at the age of just 27. And, in the curious case of Kanye West, we arguably are doing it again.

Look, I’m not going to defend Kanye West’s misogyny. Nor his defense of a certain high-profile alleged rapist. But West’s outbursts have become so extreme and so commonplace so as to clearly suggest there’s more to the story than just some publicity-seeking rich rapper. But instead, we happily share the latest hot take on the latest Kanye incident and shake our heads: “Can you believe this guy? Who the f*** does he think he is?!”

We’re not asking the questions we should be of one of the music industry’s most innovating rappers of all time. Questions like, “Is he OK? Is he getting the help he might need? Is he surrounded by people who will see to it he gets that help, should he need it, before it’s too late?”

As Amy made painfully clear, money doesn’t buy happiness. And it doesn’t buy health. And just because an artist seems to have every tool in their box to overcome whatever challenge they are facing, not everyone is so lucky.

And not everyone is brave or savvy enough to do what they need to do to face their demons. In a interview taped last year for ABC’s Nightline show, Australian pop music genius Sia sat down to explain why she has taken the unusual approach to not exposing her face in interviews, live performances or videos.

In the interview, she explains that, in 2010, she reached a breaking point where she was struggling with her budding status as a celebrity and touring musician, and how she turned to substance abuse to cope. Not exposing her face has made it possible for her to go about her life in a way that works for her.

I couldn’t help but think back to April of that year, when I was lucky enough to interview Sia over the phone for EDGE Media, an LGBT-focused news website, amid what appears will be her final proper concert tour.

Over the phone from the back of her tour bus, Sia described how she’s “scared of people” and becoming “a bit messy, shaky and anxious.” The response struck me as a bit strange and I delved further, but, at the same time, I can’t help but feel guilty that I didn’t feel more concerned for her wellbeing. I felt detached from it, an observer, even as she articulated her feelings of unhappiness:

“When I’m doing jazz hands for these thousands of people I don’t know but for some reason have become important to me, I don’t have any energy left over for my friends or family. I used to be entertaining in my private life, the class clown and the heart of the party. I was silly and would bring everyone costumes to have fun and play board games. But I have no energy for that anymore. I’m exhausted. And that’s not really OK with me. I’ve decided that I really want to give the people I love and am close to more of my energy while working out what’s best for me in the long term.”

Sia was able to figure out a way to go about her career in a way that was healthy for her.

But people like me didn’t help her do that. People like me probably aren’t concerned for ‘Ye either, just like they weren’t for Amy. Maybe we should be.