Women in Music 2016

Rewinding the Charts: 27 Years Ago, Tiffany Was 'Alone' Atop the Hot 100

It remains one of the shrewdest marketing campaigns in music history: In 1987, Tiffany Renee Darwish, better-known as Tiffany (then 16), performed shows in shopping malls across the United States to promote her self-titled debut MCA album. By visiting fellow teens at their second home, the mall – where record stores were then standard, by the way – Tiffany was able to translate her appearances into chart-toppers.

Billboard Hot 100: Nov. 7, 1987

On the Nov. 7, 1987, Billboard Hot 100, her pop/dance cover of Tommy James and the Shondells' 1967 No. 4 hit "I Think We're Alone Now" rose 3-1 on its way to a two-week reign. Parent set Tiffany spent two weeks at No. 1 on the Billboard 200 in January 1988 and, that April, was certified quadruple-Platinum by the RIAA.

Tiffany ballad "Could've Been" became the southern California native's second Hot 100 No. 1, also for two weeks, while her gender-bending cover of the Beatles' "I Saw Him Standing There" hit No. 7. In late 1988, Tiffany released her second album, Hold an Old Friend's Hand, which reached No. 17 on the Billboard 200. It yielded the No. 6 Hot 100 hit "All This Time" and a second top 40 entry in "Radio Romance."

As pop fans' tastes drifted to rap and grunge, Tiffany didn't score another Billboard chart entry after 1989 until 2007, when she posted her first of three hits on Dance Club Songs. In 2011, she starred in Syfy's Mega Python Vs. Gatoroid with fellow late-'80s teen queen Debbie Gibson. In the film, the pair (now good friends; they had no time to interact as teens, according to Gibson) mock their supposed rivalry as they battle like UFC combatants. Said Tiffany to Billboard upon the movie's premiere, "Two girls fighting? Hot!"

Now 43, Tiffany is the married mother of a 23-year-old son, Elijah, and lives in Nashville, where she runs Tiffany’s Boutique, a clothing store that sells her own designs. She still tours and is recording an album of torch songs and jazz standards.

A version of this article first appeared in the Nov. 15 issue of Billboard magazine.