"Un-Break My Heart" was everyone's favorite song to listen to while crying over a bad breakup. The year was 1996, and Toni Braxton's power ballad topped the charts, cementing her status as a global superstar. With her deep, brooding voice, Braxton ruled radio and garnered a host of Grammys.
But that was then. Fast forward 15 years and Braxton is now contemplating posing nude for Playboy to help pay the bills.
"There's nothing wrong with doing Playboy," Braxton, 45, said in an interview to air on "20/20" Friday. "The women are beautiful. I thought about it. The money was tempting, but I'm thinking, I have kids, I have a son, I have boys. What are their friends going to say? 'I saw Denim and Diesel's mom's knockers.' That's not a good thing."
So what happened that drove the singer and reality TV star from the highest of highs to bankruptcy? Twice. It turns out Toni Braxton is the poster child of Hollywood's wild rollercoaster – flying high, falling down then bouncing back.
Despite $170 million in worldwide sales, from hits like "Breathe Again" and "Another Sad Love Song," Braxton said she got a measly $1,972 royalty check from her first recording contract. In the music industry, the artist is responsible for paying back the record label for all kinds of costs including: clothes, travel, studio time and music videos.
"What happens is they give you advancement on the next record and then the next record," explained Braxton. "So you kind of stay in debt, in a sense."
That's what she said brought on bankruptcy No. 1 in 1998; that -- and a serious home decor addiction and a bank-busting flatware habit.
"I love dishes and house things, so I kind of lost it a little bit on the houseware," she said about her spending habits, admitting she slightly lost touch with reality.
From plates, to Faberge eggs, and 1,000 thread-count sheets, Braxton indulged in the "girly things."
"That's what I indulged in. I loved that part of it," she said, adding, "I'm a little odd."
Gospel Girl to R&B Diva
Braxton said she's felt odd ever since growing up with a Pentecostal preacher for a father.
"In the neighborhood we were the odd religious kids," she said. "We couldn't celebrate Christmas. … [Music] was not allowed. No secular music. … I couldn't go to the movies -- all these things were considered a sin. I didn't wear pants until I was fourteen years old. …. I had to wear hats. 'A woman should cover her nakedness.'"
Once she became an R&B star, Braxton put her Gospel image behind her and sported risqué red carpet outfits that left little to the imagination.
"I'm comfortable with my inner slut," she said. "The way I dress would be considered provocative, but I enjoy being who I am now. I'm very grateful for my childhood because it helped form who I am today. "
Armed with a new record deal guaranteeing her millions, Braxton successfully emerged from bankruptcy and returned to prominence in 2000, thanks to her hit, "He Wasn't Man Enough"
But the success was short-lived. The songstress tried changing her sound to complete with new and younger stars like Beyonce and Rihanna and her fans weren't buying it. Her next three albums only sold a few hundred thousand copies each.
"Those albums—that's like that one-night stand that you don't want to talk about," she said. "You don't want anyone to know about those records that didn't do well. I had a few of those. Definitely a few."