How a Shy 16-Year-Old Rihanna Landed the Contract of Her Dreams

At the age of 16 years old, Robyn Rihanna Fenty left her home on the Caribbean island of Barbados and signed the contract of her dreams with Jay-Z.

According to author John Seabrook’s “The Song Machine,” Fenty scored an audition with Def Jam record producer Evan Rogers in the winter of 2003.

“I said to myself, ‘If that girl can sing,” then — holy sh**,” Rogers told Seabrook. “She had such a presence! … Her makeup was perfect, and she had these capri pants and matching sneakers, with her green eyes and her long supermodel neck.”

At the time of her audition, Fenty was 15 years old, went by her first name Robyn, and had no formal training in dance or music.

The following year, Fenty recorded the catchy tune “Pon de Replay.” The demo was sent to several record labels and when it reached Def Jam, it was sent all the way to Jay-Z, the president of the label.

Upon hearing her voice, Jay-Z flew her from Barbados to New York City to meet with executives at the label.

“I was very shy … I was cold the entire time. I had butterflies. I’m sitting across from Jay -Z. Like, Jay-Z,” she would later say in a 2007 interview with the Observer, according to Seabrook.

gettyimages 79696374 How a Shy 16 Year Old Rihanna Landed the Contract of Her Dreams

Rapper Jay-Z (L) and singer Rihanna accept an award during the 50th annual Grammy awards held at the Staples Center on February 10, 2008 in Los Angeles, California. (Kevin Winter/Getty Images)

After her audition, Jay-Z was so impressed that he reportedly asked, “So, what do I have to do to get you guys to cancel all your other meetings?” He was so determined to sign her that he said, ” There are only two ways out. Out the door” — if she signed the record contract — or “through this window” if she didn’t.

And so, the lawyers worked out the contract details until 3 a.m. and she prepared for her future career as Rihanna.

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