Jay-Z And Rihanna's Relationship Explained

It seems like it was a different time entirely when Rihanna, born Robyn Rihanna Fenty, was one of the biggest R&B and pop singers on the charts. Yes, the Barbadian business mogul we know now — worth $600 million as of 2019, according to Forbes — actually has nine Grammy Awards, 14 number one hits on the Billboard Hot 100 charts, 12 American Music Awards, and one Michael Jackson Video Vanguard Award. Before she was creating award-winning fashion labels and beauty brands, she was a 15-year-old singer trying to get discovered. According to Business Insider, record producer Evan Rogers was the first to discover the young singer while vacationing in Barbados. 

"She had such a presence!" Rogers said. "Her makeup was perfect, and she had these capri pants and matching sneakers, with her green eyes and her long supermodel neck." He added, "I said to myself, 'If that girl can sing, then holy sh*t!" By December 2004, Riri recorded her first single "Pon de Replay" and sent the track off to record labels. One of those labels was Def Jam, and her demo went all the way into the hands of the president of the label, Jay-Z. 

Hip-hop mogul Sean Carter aka Jay-Z knew he had a gold mine in his hands when he first heard Rihanna's demo of "Pon de Replay." In fact, he was so certain that he wanted to sign her that he flew her out to the United States to meet him and other executives at the Def Jam label, according to Business Insider. Per the outlet, Rihanna told the Observer in a 2007 interview that she was "very shy" and "cold the entire time," but that didn't stop her from giving a stellar performance.  

Jay-Z was so moved by her presence and desperate to sign her that Rihanna recalled him saying, "There's only two ways out. Out the door'" — if she signed the contract — "'or through this window'" if she didn't." As history goes, she signed with Def Jam that same night and began cranking out hits under the tutelage of one Mr. Carter.  

As soon as Rihanna inked her first contract, she immediately began creating hit after hit. The young singer's mentor Jay-Z even featured on a few of her biggest tracks including 2008's "Umbrella" and 2010's "Run This Town" — which also featured Kanye West — and 2011's "Talk That Talk." Of course, each song won its own accolades and awards over the years, including Grammy Awards and MTV Video Music Awards. 

It seemed as though Rihanna was following in her mentor's steps when it came to transitioning from music to business. She's the proud owner of Fenty Beauty, Fenty Skin, Savage x Fenty, and other fragrance lines and ready-to-wear fashion lines, while Jay has founded everything from a sports management agency to his own music streaming platform Tidal.

But in a 2019 interview with Interview magazine, the queen of lingerie spoke about her love for putting herself first before all else. She said, "My career is my purpose, and it should never feel like anything other than a happy place." 

This may be why fans may have to wait a bit longer for the notorious ninth studio album, nicknamed on the internet as "R9," to be released. Whenever the Navy finally gets the new album or the world gets another beauty or fashion line, Jay-Z will surely be in her supportive corner. 

Rihanna and Jay-Z are clearly close. They've been mentor and mentee, boss and employee, and joint collaborators. So, the burning question is, has their relationship ever crossed the line? Have they ever been friends with benefits? Gotten a little jiggy with it? There have certainly been plenty of rumors, and enquiring minds need to know.

J Randy Taraborrelli was certain that Rihanna once had some of Brooklyn's Finest under her umbrella. Taraborrelli spilled the alleged JayRi tea in his autobiography, "Becoming Beyoncé: The Untold Story." In the "explosive" book, the author claims that Jay-Z and Beyoncé Knowles split in 2005 when he was working on promoting Rihanna's debut single, "Pon De Replay." Bey allegedly wasn't comfortable with the fabricated story of Jay and Rih dating, believing there was more than a working relationship between the two. "They spent maybe a year apart from each other because Beyoncé just wasn't sure of what to make of the situation with Rihanna," Taraborrelli claimed to Entertainment Tonight.

Rihanna's former publicist set the record straight. He confessed to inventing the rumor and then leaking it to the tabloids to see "if the spaghetti would stick" and help boost the rising star's profile. "I didn't think it would be this big story," Jonathan Hay told New York Daily News. "I'm ashamed that I'm even talking about this. I just want to put this rumor to rest once and for all."

Jay-Z cannot stop making it rain compliments on Rihanna. The mega mogul is her biggest cheerleader, shouting Ri's praises from the rooftop whenever he can. A cynic might note that Jay-Z's Roc Nation manages Rihanna, and his venture capital firm is a significant investor in her beauty line, Fenty. 

"Rihanna is a generational talent, a woman of humble beginnings who has surpassed expectations at every turn," Jay-Z announced in an NFL press release ahead of Rihanna's Super Bowl 2023 halftime show. "A person born on the small island of Barbados who became one of the most prominent artists ever. Self-made in business and entertainment." And it goes both ways between these two. Rihanna admits to fangirling over Jay-Z when she first met him at 17. "I was like: 'Oh God, he's right there, I can't look, I can't look, I can't look!'" She told The Guardian. "I remember being extremely quiet. I was very shy. I was cold the entire time. I had butterflies. I'm sitting across from Jay-Z. Like, Jay-Zee. I was star-struck."

However, despite his never-ending Rihanna props, the rapper knows better than to try and tell the formidable Ms. Fenty how to run her town. "That's not my place," Jay-Z told Hot 97's Angie Martinez back in 2013. "I can't control the outcome of her life. I can't intervene, I can give advice when asked, and that's it."

Rihanna admits to having a tough time when she first signed with Def Jam. And the leading cause of it: Rumors. "At first, it was funny. Then it was frustrating. Because it got really intense where people just weren't letting up," Rihanna told The Guardian. "Then it turned into a 'beef' between me and Beyoncé. I was like, 'Where are these people going with this? This is crazy.'" Rihanna insisted that Beyoncé's always been "supportive," adding, "She's so great."

In 2010, Rihanna gushed to Tyra Banks about her first Bey encounter. "I could not speak," she admitted. "That's somebody I really looked up to for a long time." Rihanna said Beyoncé passed on some good advice, telling her "to always have fun and be in control."

Rihanna also confessed that she dreams of Beyoncé getting into her undies. "I mean, Beyoncé got body," she told E! News when asked who she would like to wear her lingerie brand, Savage. "Beyoncé in anybody's panties gonna set it off, but I would rather them be mine." In case of any lingering doubts, Rihanna shot dead the Beyoncé feud rumors once again, admitting she isn't here for made-up drama. "Here's the deal, [gossips] just get so excited to feast on something that's negative. Something that's competitive," she told Vogue. "Something that's, you know, a rivalry. And that's just not what I wake up to."

Rihanna and A$AP Rocky's beautiful baby boy is still a newborn, however, there's no question that he'll have amazing mentors in the Carter kids. Rihanna already goes way back with Jay-Z and Beyoncé's first born, Blue Ivy Carter, who is 11 years old now. "Welcome to the world, princess Carter! Love Aunty Rih," she tweeted when news broke of the new edition's arrival.

In 2017 Rihanna was back on social, spreading the joy once again after Beyoncé and Jay-Z announced they were expecting twins, Rumi and Sir. "So excited about this news!!!!" she captioned the iconic pregnancy photo of the "Cozy" singer on Instagram. "Congratulations to you, Beyoncé's, and my big bro Jay!!!!" 

For her own pregnancy announcement, the makeup mogul took a page from Beyoncé's playbook and insinuated she was expecting during her Super Bowl 2023 performance. The announcement was similar to Bey's during her 2011 MTV Awards performance where she revealed she was expecting.

HuffPo editor Phillip Lewis was on hand to capture Jay-Z and Blue Ivy as they attended the big game to cheer on Auntie Rih during her halftime performance. The daddy and daughter duo wore matching blue sweats and black shades; fans even caught Jay having to play photographer to tween.