The daughter of Alfred, a black aeronautical engineer from Venezuela, and Patricia, an Irish-American opera singer, Carey is just 3 years old when her parents split. As a mixed-race couple that moved from one all-white Long Island suburb to another, "They went through some very hard times before I was born," Carey later relates to PEOPLE. "They had their dogs poisoned, their cars set on fire and blown up. It put a strain on their relationship that never quit...They just fought all the time."
Soon after graduating from high school, aspiring singer Carey, then working as a coat-checker/waitress in Manhattan, meets Sony Music mogul Tommy Mottola at a Columbia Records party. Mottola snatches her demo tape from another music scout and, after listening to it on his drive home, decides to track Carey down.
Carey knocks it out of the park with her self-titled debut album, which stays atop the Billboard albums chart for several weeks based on the strength of its four No. 1 singles. She wins two Grammys the following February – Best New Artist and Best Female Pop Vocal Performance for her debut single "Vision of Love."
Carey proves naysayers wrong when she finally performs live on MTV's Unplugged. Singing her own hits, including "Emotions," the chart-topping single off her album of the same name, Carey impresses critics and stands out with her rendition of the Jackson Five classic "I'll Be There." The show's success convinces Sony to release the performance as an album in June, which goes platinum.
Mottola makes her a star and she makes him her husband. Their lavish New York City wedding is attended by Barbra Streisand, Bruce Springsteen and Robert De Niro, who serves as an usher. Carey wears a Vera Wang gown with a 27-foot train that requires six women to lift it. With 200 security personnel, 300 guests and a wedding party that included 47 flower girls, the final tab for the shindig comes to $500,000.
Carey's next album, Music Box, is released to strong sales, making it her first No.1 album since her debut. The first single, "Dream Lover," spends two months at No. 1.
Changing her usual style, Carey combines more modern R&B and hip-hop influences on her latest album Daydream, teaming up with Wu-Tang Clan rapper Ol' Dirty Bastard on a remix of her song "Fantasy." "Everyone was like, what are you crazy?" she tells EW about reactions from her record label. The bold move pays off, when Daydream goes multiplatinum.
Carey meets 22-year-old Yankees shortstop Derek Jeter at a benefit for the Fresh Air Fund. Although she's still married to Mottola, newspapers begin to question if Carey and Jeter are more than just friends, a piece of gossip which both parties deny. Two years later Carey owns up to dating the baseball star.
Although they remain committed to preserving their working relationship, Carey and Mottola decide to separate, with the singer moving out of their $10 million Bedford, N.Y., mansion. Carey embraces her newfound independence, creating Butterfly, her most risqué and independent album to date.
Carey becomes a fixture in New York nightlife, frequenting trendy Manhattan hangouts such as Diddy's restaurant, Justin's, and vamping it up in shorter skirts and stiletto heels. "I went out to a club, and no one had seen me in years," she says of her days away from the protective Mottola.
BIOGRAPHY (top to bottom): CLASSMATES YEARBOOK ARCHIVES; Bill Swersey/Liason; REUTERS/Landov/Corbis; amazon.com ; Dave Allocca/DMIPhoto; amazon.com; Aubrey Ruben/UAR/London Features