The main one simply being: Why?
A new documentary called "Whitney" aims to answer that and more as it sheds light on how the superstar plummeted to the personal low that contributed to her death.
The singer's sister-in-law, Pat Houston, who served as a producer on the documentary, sat down with TODAY's Sheinelle Jones to talk about the film.
In the trailer, Whitney herself can be heard to say, "There were times when I would look up to God and I'd go, 'Why is this happening to me?'"
Pat attempted to answer that.
"Why? You know, it's the choices that you make," she said during her TODAY chat. "We look at celebrities like they're immortals and they're not. And the expectation that she's supposed to be this perfect person, that's a lot of pressure for one to have to deal with."
As Whitney's reputation as a perfect vocalist took a backseat to headlines and gossip about her downward spiral with drug use, the pressure intensified.
"It was a burden," Pat explained. "A few days before she passed that's what she talked about. 'Why do people judge me?'"
In "Whitney," family members open up about the star's struggle with drugs and how surprisingly early that began — even alleging that one relative gave her marijuana and cocaine for her 16th birthday.
According to Pat, "Back then, everyone was trying it and doing drugs. It was a recreational thing. They weren't thinking. They were just thinking about having fun."
But, eventually, at least some of those around Whitney realized it wasn't fun anymore.
"There were interventions for her, " her sister-in-law said. "Everybody always went to her."
Another major allegation in the film is that both Whitney and her brothers, Gary Garland and Michael Houston, were sexually molested by a cousin in their youth — the late Dee Dee Warwick, sister to legendary singer Dionne Warwick.
"It's such a very sensitive subject," Pat said, adding no further details but explaining why. "I still have my mother-in-law and Dionne, who are still here with us — and they're both very honorable women."
TODAY reached out to both Dionne Warwick and Sissy Houston regarding Dee Dee Warwick and the molestation allegations. Sissy Houston was "declining all interviews and comments." There was no response from Dionne Warwick.
The details all point to difficulties that began even before Whitney's meteoric rise to fame. But despite the addiction and darkness she lived with, according to her family members, her final days — before she was found dead in a hotel bathtub at the age of 48 — included joy and happiness.
So what happened?
"Only her and God knows that," Pat said. "I'm at peace because I know she's at peace. She doesn't have to deal with all this anymore. And she was given to us for one moment in time. She served her purpose.
"Whitney" hits theaters on July 6.