Rihanna and Jay-Z are both self-made billionaires and have had a mutually beneficial business relationship for over 15 years. The Bajan singer and Brooklyn rapper have made music together and individually had ventures outside of music that have propelled them into wealth. However, before signing Rihanna, Jay was a tad sceptical of her abilities and was tremendously hesitant to sign the vocalist.
Rihanna first came to the attention of Jay-Z (real name Shawn Carter) after he received a demo from Evan Rogers, a renowned producer and songwriter in the music industry. Rogers had heard the artist while he was in Rihanna’s home country of Barbados. Upon hearing her sing, the producer helped her record a compilation of songs that would end up falling into the lap of Jay-Z.
Rihanna (real name Robyn Fenty) was only a teenager at the time. However, the music industry veteran saw great potential in her. Speaking to Rolling Stone magazine in 2011, Rogers described how he perceived Fenty upon first seeing her, detailing, “She was fierce, like Kobe Bryant. I knew she was a star.”
After hearing her, Rogers aided Fenty in assembling her first set of professionally recorded songs. However, the businessman knew if she was going to make it big, he would have to get the tracks in front of US-based major labels, one of which was Def Jam. During the early-2000s, Jay-Z was the acting president and CEO of the label, and as one of the label’s co-founders, Carter was responsible for discovering new talent.
Having just become president of the organisation, when the Brooklyn rapper was given the Bajan singer’s demo, he wasn’t impressed and believed that songs such as ‘Pon De Replay’ were too big for her. However, with Rogers insistent that the Fenty Beauty billionaire was a gem, Carter flew her to New York to audition for him and his Def Jam counterparts in 2005. Before Jay-Z decided to grant her an audition, he played the demo for the renowned DJ and A&R Cipha Sounds.
In a 2021 interview with Michael Yo, the DJ detailed the events leading up to the Brooklyn rapper finally extending Fenty an invitation, disclosing, “The night before, me and Jay-Z had an argument about her! He was like, ‘I don’t know. It might be just one song.’ I’m like, ‘No, I’m telling you, Jay, this is why you have me around. My ear is your ear. I’m the A&R.” The DJ then revealed how he and Carter had much deliberation concerning Rihanna.
He continued, “We had a big argument; we always talk about it to this day!” However, enough people within the company had told the Brooklyn rapper that, regardless of what he thought Fenty was not destined to be a one-hit-wonder. After flying her to the US and hearing her in person, Jay-Z was blown away by her vocals when he heard her in person and asked Rogers, “So what do I have to do to get you guys to cancel all your other meetings?”
The label executive LA Reid was also stunned and, similarly, was eager to sign Fenty following her audition. As a result, Reid told Jay-Z not to let Rihanna leave the building until she penned a contract. While the executives figured out the best deal for Fenty and how they would proceed to market her, Rihanna waited in Jay-Z’s office until 3am. After coming to their conclusion, they got the ‘Umbrella’ singer to sign her deal with Def Jam, which included six full-length studio albums.
To this day, Rihanna is an icon in music, and since her breakthrough in 2005 with ‘Pon De Replay’, the musician has grown to become a beloved act in the US and across the world. You can listen to the song which was the lead single of her debut album, Music For The Sun, in the video below.