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Whitney Houston biography, ‘Didn’t We Almost Have It All,’ examines how we all tortured a massive, but troubled talent

Author Gerrick Kennedy says he tried to balance critique and grace

Gerrick Kennedy remembers the living room of his home growing up in Cincinnati. If the TV was on, it was either on MTV or BET — if The Bodyguard wasn’t on. Whitney Houston, the subject of Kennedy’s new book, Didn’t We Almost Have It All: In Defense of Whitney Houston, was always nearby. Even if the world he lived in and the world Houston dominated with chart-topping hit after hit felt light-years apart.

“All of this felt untouchable. All of the music industry, all of the film industry, all of TV, it all felt like this very faraway land that didn’t actually really exist because all my friends, like me, were all poor,” Kennedy told me. “We never really had those aspirations for any of this. It was never something that we ever thought about. It was something that was just purely an escape.”

Publishers Weekly calls Kennedy’s book “stirring” and a “must-read for fans.” He calls it a “love letter,” but he isn’t afraid to be critical … of everyone.

“Of her, of us, of the music industry, all of it,” he said. “There were some days that were much tougher than others in which I got to certain parts that I wanted to write about. But I did ultimately want it to be this conversation between us and how we treated her.”

Publication coincides with the 10th anniversary of Houston’s death at 48 from an accidental drowning in a bathtub at a hotel in Beverly Hills, California. Kennedy, who used to cover music and pop culture for the Los Angeles Times, recently talked with The Undefeated about the grief he had to overcome to write the book, how the world attempted to dictate Houston’s Blackness to her, and how chronicling one of the most celebrated and emotionally battered pop icons changed him as a writer and fan. He’s resolute on one point: A lot of us owe Houston an apology.

This interview has been edited for clarity and length.

How did you see your personal responsibility in writing this book?

The idea of personal responsibility is really heavy because I kind of was holding a couple different things as I was writing. There was the part of me who was a fan who then was able to document this woman when I was at the L.A. Times. Unfortunately, there was a short window of where I was able to just write about her when she was here on earth, and it wasn’t always great. I remember some of those shows on that last tour that she did. They were not strong. At a publication, this is what’s trending. You have to write about it. So to go from that to then meeting her for the first time and she then dying two days later, there just was this burden that I had always kind of felt in relation to how people saw me in the story because I became a source. I became a part of it. I couldn’t change the fact that I was one of the last people who saw her alive, so then I had to say what that day was over and over and over and over.

But I saw this as an opportunity to release a lot of my own grief. She is someone I love tremendously. She is someone whose career I have followed. She’s someone who I admire. She is the reason why I love so many other women in this industry. … So, it was a lot of emotions wrapped into that, because I also wanted this book to be really honest and I felt like, in order to be honest, we needed to have a conversation with each other about how we treated this woman when she was alive. And yes, she also made her own choices, obviously, so you have to hold her accountable to her choices as well.

Why was the discussion around Houston and race so important?

Having a conversation around Whitney and race, I honestly could not believe we were not doing it more. When you see the totality of how she was seen by everybody, but then how she was seen by Black people about her Blackness. And then also how she was seen by white people about her Blackness. … We can acknowledge that she broke these grounds, blah blah, but we never really put into context what that meant, but also what it cost her to do this, what it cost her to be young and Black and having a mostly white industry be the ones to shape how people perceived her as an artist, as a woman, but a lot of them also wanted to shape how we saw her as a Black woman.

When you think of the conversations around Whitney and race and that she wasn’t Black enough, which is what we did so much of. And this was us. This was our people doing that. This was Al Sharpton doing that, you know what I mean? This was radio disc jockeys doing that. This was rooted in our community having this conversation that she wasn’t Black enough because she dared to sing these pop ballads. I think when you had these two separate conversations happening, you got Black people saying, ‘You’re not Black enough,’ you got white people that’s like, ‘Yeah, she could be doing this and this and this,’ and then she gets with Bobby [Brown], and then we start doing the inverse of that of being like, ‘Oh, well, you’re a little too ghetto now.’ Every time that we saw Nippy, which was always who she was when she didn’t code-switch, we started then having the shift to like, ‘Oh, well, actually it’s too much now.’

How did writing this change you as a fan?

As a fan, it helped me have a lot more grace toward the moments where I felt let down by her. She was constantly battling the ways in which she was being perceived. She was constantly battling anytime she showed a part of herself, which was, ‘I don’t feel like putting on makeup,’ and ‘I like to dress like this,’ and now you’re going to call her a crackhead when she does it, which is what we were doing. The ways that we were so incredibly cruel to her that we laughed. All of us did. Any person who said they didn’t laugh at any of those jokes, you’re a liar.

Even the moments where she was cruel to herself or to others or whatever, I extend a little bit more grace in writing this. She paid for how incredible ‘I Will Always Love You,’ and ‘The Star-Spangled Banner.’ She paid for that for the rest of her life because she couldn’t hit those notes the exact same way she did in ’92, forever. We reminded her of that every time she walked on the stage, every single time. And that is terrible. We would never tell Adele, ‘Remember that time you messed up at the Grammys?’ We would never tell Beyoncé, ‘Oh, yeah, Super Bowl was great, but remember when you fell down the steps on that tour 10 years ago?’ We don’t do that to people, but we did it to her and we did it so cruelly.

When you hear that it’s the 10th anniversary of Whitney Houston’s death, what goes through your mind?

I try not to think about that weekend a lot, and I know the 10-year anniversary is coming up. … But I have been able to, through the book, arrive at the same place that I arrived at when I think of Aaliyah at this moment, or Biggie at this moment, or Tupac at this moment. Or all these people who have meant so much to us and the fabric of not just American culture, but Black culture and Black music and the way that I see it as a moment of being able to just celebrate their greatness. With Whitney, it’s that I’m really grateful that we’ve moved to a place that we celebrate her more than we tear her down. I like the fact that we are getting some level of discovery of her music through younger generations by these dance remixes that happen.

I ultimately want this book to be the first of many that people do. Because there can never be enough Whitney, because she did so much for all of us. 

Justin Tinsley is a senior culture writer for Andscape. He firmly believes “Cash Money Records takin’ ova for da ’99 and da 2000” is the single most impactful statement of his generation.