Only a few stars can be recognized by their single name: Madonna, Prince, Cher, and, of course, Tiffany Playboy from 1980s teen pop music.
Three decades ago, Tiffany achieved international success with such hits as “Coulda Been” and her cover of “I Think We’re Alone Now.” However, long before this single-named celeb sold four million copies of her debut album, 10-year-old Tiffany Darwish was singing in bars in Nashville bars.
“I wasn’t allowed to be there,” Tiffany recalls in the above video interview with Oprah: Where Are They Now? “Nobody really wanted to give me a record deal; they were kind of like, ‘Come back when you’re older.'”
After several years, Tiffany Playboy met George Tobin, who would become her producer, and her career as an artist began to take shape. But first things first: selecting the perfect name!
“They wanted to call me Tiffany Williams at first,” she laughs. “But that’s just not acceptable!” So she simply replied: “Why not just Tiffany?”
At 15 years old, Tiffany embarked on a tour of shopping malls across America that quickly turned into chaos. “When it got out of hand and people were being shoved against barricades and it wasn’t safe, I actually started crying,” she recalls.
After her debut album reached No. 1 on the Billboard charts, Tiffany felt pressure to maintain that success. “The next album,” she recalls, “you’re rushed into the studio to re-record something and get it out there quickly… [but] that kind of took away some of its charms.”
Tiffany continued releasing albums, though none quite achieved the same commercial success as her initial release. Over the next several years, Tiffany’s career experienced more ups and downs as she matured and developed as an artist. After decades of fame had passed, Tiffany became determined to shed its “teen queen” image.
“I feel like I’ve always been put in a box – that I’m Tiffany from the mall tour,” Tiffany confides. “And then there was Playboy.”
In 2002, Tiffany posed nude for Cosmopolitan magazine – much to the disbelief of many. But as she now explains, there were several compelling reasons behind it that led her to do it.
“Divorce can be a devastating experience, taking your confidence away,” she recalls. “[Posing for Playboy] was an instant confidence boost and added shock value.”
“Everyone wants to talk to me,” Tiffany shares. “So if I can turn that into music and say ‘Yeah, remember that little thing I do…?’, then it works.”
“Oprah: Where Are They Now?” airs Sundays at 9 p.m. ET and returns with all-new episodes in February. Make sure to catch OWN on your television screen
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