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She waited in Jay Z's office till three in the morning to get lawyers to draft up a contract because he wanted to prevent her from signing with another label.
Looking back on the audition and meeting Jay-Z, Rihanna explained that "when we first got there, I was shaking.
She recorded the demo over the next year intermittently, due to Rihanna only being able to record during school holidays.
"Pon de Replay" and "The Last Time" were two tracks recorded for the demo tape, which were eventually included in her debut album Music of the Sun.
Brown played the demo tape for rapper Jay-Z, who had recently been appointed as president and Chief executive officer (CEO) of Def Jam.
When Jay Z first heard the track "Pon de Replay", he felt the song was too big for her, saying "when a song is that big, it's hard [for a new artist] to come back from. Reid left it to Jay Z and his team to close the deal which resulted in a six-album record deal with Def Jam.
Born in Saint Michael and raised in Bridgetown, she first entered the music industry by recording demo tapes under the direction of record producer Evan Rogers in 2003.
She ultimately signed a recording contract with Def Jam Recordings after auditioning for its then-president, hip hop producer and rapper Jay Z.
In 2005, Rihanna rose to fame with the release of her debut studio album Music of the Sun and its follow-up A Girl like Me (2006), which charted on the top 10 of the U. Billboard 200 and respectively produced the hit singles "Pon de Replay" and "SOS".
She displayed her Bajan moves on the Global Citizen stage earlier in the evening.
Not wanting to end the night there, the pop diva stylishly caught up with her model gal pal in the Big Apple on Saturday.
After releasing four Recording Industry Association of America (RIAA) platinum-certified albums, including the Grammy Award winner Unapologetic (2012), she was recognized as a pop icon.