Here's how badly Jay Z wanted to sign a bashful 16-year-old Rihanna to a record deal

In the winter of 2003, then-15-year-old 
Robyn Rihanna Fenty scored an audition with record producer Evan Rogers while he was vacationing in Barbados with his wife.
“I’ll be down at the beach and somebody will come up to me and start singing — it’s like that,” Rogers said according to author John Seabrook’s “The Song Machine,” which explains the process that has created some of the biggest hit songs.

Rogers recalls the moment Robyn Rihanna Fenty walked in, “… I said to myself, ‘If that girl can sing,” then — holy shit!”

“… 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,” Rogers told Seabrook.

However, Rogers immediately thought, “She probably can’t sing, because usually it’s the pretty one who can’t,” Seabrook wrote.

But as we all know, he was wrong.

“…The whole time I’m thinking, ‘OK I have to follow-up meeting with this one,'” Rogers told Seabrook.

Meanwhile, Robyn’s mother was ‘low-key’ about the opportunity.

“She didn’t really get that her daughter had anything special. She was like, ‘Well, if you see something. I just want her schoolwork to be done. Education is very important,'” Monica Fenty reportedly said to Rogers.

Fifteen year old Robyn, who had no formal training in dance or music, told Rogers during their meeting that being in the music business is “all I’ve ever wanted to do.”

Similar to Britney Spears and Kelly Clarkson, Robyn was eager to escape from her sometimes violent childhood.

“… It was more likely a much more urgent need to escape from the anxieties of a violent home life into the illusion of security and boundless love that a life onstage seemed to offer. That desire, more than any inborn talent, is what fans will connect to, and that is what record men look for in a new artist. It’s the one thing they can’t manufacture.”

In December 2004, Robyn recorded the Caribbean jam, “Pon de Replay” and the song was sent off to several record labels. 

When the demo reached Def Jam it was sent all the way to Jay-Z, the president of the label. Robyn was flown to meet with Jay-Z and a few other 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.

She knocked her audition out of the park which triggered Jay-Z to say, “So what do I have to do to get you guys to cancel all your other meetings?”

According to Seabrook, Jay-Z wouldn’t let her leave the building until she signed with the label.

“They were there until three in the morning while the lawyers worked out the details. Fenty later recalled Jay-Z saying, ‘There’s only two ways out. Out the door'” — if she signed the contract — “‘or through this window'” if she didn’t.

At the age of 16 years old, she signed the contract 0f her dreams and left through the front door.

RihannaGetty ImagesRihanna and Jay-Z in the audience during the 52nd Annual GRAMMY Awards held at Staples Center on January 31, 2010 in Los Angeles, California.

Here’s Rihanna’s debut song:

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