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Tiffany’s major breakthrough came when she participated in the television talent show, "Star Search." Although she did not win, Tiffany gained invaluable experience on stage, learning how to connect with her audience beyond just her vocal talent. Soon after, she transitioned from country music to pop, inspired by artists like Stevie Nicks.
Tobin quickly secured a record deal for Tiffany with MCA Records, and their initial efforts culminated in the release of her self-titled debut album in 1987. The first single, however, missed the charts, leading her team to strategize aggressive promotional tactics. They launched a nationwide mall tour, where Tiffany performed several sets a day, ultimately raising her profile and sales—though often at the cost of her artistic integrity and image.