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Rihanna has entered a whole new phase of life, recently announcing that she’s expecting her first child with her boyfriend, A$AP Rocky. Making headlines is nothing new for Rihanna, who has been a superstar since she was a teenager.

Many fans love Rihanna for her fearless nature, her groundbreaking businesses, and of course, her chart-topping music. However, well before Rihanna was breaking records all around the world, she was making waves in her home country of Barbados. As the singer once revealed in an interview early in her career, she won a beauty pageant after receiving a dare from her friend group.

Rihanna was born in Barbados in 1988. As a child, Rihanna was influenced by reggae music and island sounds, developing a signature singing style that is all her own. She was discovered by a music producer when she was still a teenager and moved to the United States to start work on a recording career. Her first two albums, “Music of the Sun” and “A Girl Like Me” initiated her rise to success, but it was her 2007 album, “Good Girl Gone Bad” that made Rihanna a huge star.

Even as Rihanna continued to develop her music career, she showed a passion for other endeavors as well, outside the music business. Her beauty brand, Fenty Beauty, launched in 2017 to immediate acclaim. Fenty Beauty has expanded over the years, with critics and fans praising the cosmetics line for its inclusivity and commitment to providing makeup for every skin tone. Rihanna has also dabbled in acting, appearing in movies like Battleship and Ocean’s 8

When did Rihanna take top honors at a beauty pageant?

Singer/actress Rihanna attends the World Premiere of OCEANS 8 June 5, 2018 in New York.
Rihanna | Angela Weiss/AFP via Getty Images

These days, Rihanna has mostly stepped back from the world of music and is focusing on her clothing and cosmetics business—as well as on her growing family with A$AP Rocky. However, fans are as invested as ever in her life, and in the story of how she became famous. Notably, early on in her career, Rihanna opened up about a particularly memorable contest that she once won. According to Insider, Rihanna actually entered a local beauty pageant when she was 15 years old.

Rihanna ended up winning the pageant, earning the title of Miss Combermere after performing Mariah Carey’s hit song “Hero.” While her beauty pageant career ended with that particular performance, Rihanna hasn’t been shy about discussing her experience in the pageant.

What did Rihanna say about preparing for her beauty pageant victory?

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In 2007, the same year that her album “Good Girl Gone Bad” was released, Rihanna sat down with the Daily Mail for an in-depth interview, where she discussed her rise to fame – and the notorious beauty pageant performance. “I kind of laughed at these stupid pageants,” Rihanna revealed, noting that she had previously joined the local cadets and risen to the rank of corporal, thanks to her dedication.

“But my friends at school dared me to do it,” the young singer said, “and my military training came in handy for learning to balance books on my head for the catwalk.” The year that she won the pageant, 2004, proved to be a big one for Rihanna, since she was discovered by producer Evan Rogers later that year, kickstarting her ascent to fame in the music business. A multi-talented artist, beauty, and fashion mogul, Rihanna has done it all – and has kept a sense of humor all the while.