Rihanna, born as Robyn Rihanna Fenty, began her career as a musician and entertainer when she was around 15.

Now 33, the ‘Umbrella’ songstress is officially a billionaire and the wealthiest female musician, and the second-richest woman in entertainment after Oprah Winfrey.

The last two decades has seen Rihanna rise from strength to strength, adding actress and businesswoman to her impressive résumé.

But how did Rihanna get to where she is today? Here’s everything you need to know about her remarkable rise to the top.

Rihanna is a billionaire, the wealthiest female musician, and the second-richest woman in entertainment. (GC Images)

How did Rihanna’s career start?

Growing up listening to reggae music in her native Barbados, Rihanna dropped out of high-school when she was 16 to pursue a career in music.

In 2003, alongside two of her classmates, she formed a musical trio that landed an audition with American record producer Evan Rogers — known for working with Christina Aguilera, Boyzone, *NSYNC and many more international A-listers.

Of the audition, Rogers told Entertainment Weekly, “The minute Rihanna walked into the room, it was like the other two girls didn’t exist.”

After a private audition where she performed ‘Emotion’ by Destiny’s Child and ‘Hero’ by Mariah Carey, Rihanna’s mother Monica, an accountant, was invited to a second meeting and then Rihanna was invited to go to the United States to record demo tapes, with the intention of sending them to record labels.

Fitting recording sessions in between school holidays, Rihanna was eventually signed to Syndicated Rhythm Productions.

She auditioned for Jay-Z, the then-CEO of Def Jam Recordings, performing her future single ‘Pon de Replay’ — the first time Jay-Z heard Rihanna’s ‘Pon de Replay’ demo, he felt it was too much for her, but after she performed it for him in person, he became absolutely certain that Def Jam needed to sign her.

L.A. Reid even instructed Jay-Z to not let Rihanna leave the building until she had signed the contract, and Rihanna waited until 3am for the lawyers to draft up the deal, because the rapper wanted to prevent her from signing to another label — she signed, relocated to the United States, and in 2005, ‘Pon de Replay’ was released, peaking in the top five in fifteen countries.

Her debut album Music of the Sun was released later that year, followed by A Girl Like Me in 2006. Good Girl Gone Bad (2007) propelled her into worldwide stardom, and was closely followed by Rated R (2009), Loud (2010), Talk That Talk (2011), Unapologetic (2012) and Anti (2016).

In addition to various world tours, Rihanna’s CV is also padded with acting credits, with appearances in films Bring It On: All or Nothing (2006), Battleship (2012), This Is the End (2013), Ocean’s 8 (2018) and Guava Island (2019) — only a few of the titles where she flexes her Hollywood muscles.

Rihanna at the 2015 Met Gala. (Getty)

What is Rihanna doing now?

Despite teasing her fans with the possibility of new music, the mezzo-soprano has not released any new tracks since her 2016 Anti album.

Instead, she’s been focusing her attention on expanding her business portfolio. She has her own record label Westbury Road — the same name as her residence in Barbados — that was established in 2005. Rihanna is also a stakeholder in music streaming service Tidal.

In 2015, Rihanna and Benoit Demouy started Fr8me, a Los Angeles-based beauty and stylist agency. Rihanna also owns photo agency ‘A Dog Ate My Homework.’

Rihanna is a big player in the beauty game; alongside various fragrances, Rihanna launched cosmetics company Fenty Beauty in 2017, which sits under LVMH’s Kendo Brands. It’s been praised heavily for the diversity in products, particularly when it comes to its wide range of shade options, which are not an industry standard. Rihanna also launched Fenty Skin in July 2020.

No stone is left unturned by this mogul, who is also a heavy hitter when it comes to fashion. Rihanna’s inclusive lingerie line Savage X Fenty launched in 2018, and is critically acclaimed for its wide size and shade range, made for bodies of all tones and sizes.

Rihanna made history as the first woman of colour to launch a fashion house, Fenty, under luxury fashion group LVMH in May 2019, however due to COVID-19, the billionaire and LVMH decided to “put on hold” Fenty and focus their efforts on continuing to build Savage X Fenty.

Rihanna purposely uses her surname for her business ventures that are not related to her music career so fans and consumers don’t amalgamate the two. In 2019, she sued her estranged father for his commercial use of the Fenty surname, alleging that Fenty Beauty was damaged commercially by her father’s company through his misrepresentation of it being affiliated with her.

A$AP Rocky confirmed his and Rihanna’s relationship in May 2021. (Samir HusseinWireImage)

Is Rihanna in a relationship?

Yes! Rihanna is dating A$AP Rocky.

Over a year after sparking dating rumours, the 32-year-old rapper confirmed his romance with the ‘Where Have You Been’ singer in an interview with GQ.

“[It’s] so much better when you got The One. She amounts to probably, like, a million of the other ones,” he told the publication of Rihanna in May 2021.

“I think when you know, you know. She’s The One.”

Rocky — real name Rakim Mayers — also referred to Rihanna as “my lady” and “the love of my life” in the interview, and said he sees children in his future.

The duo have been friends for years, with Rocky featuring on Rihanna’s 2011 single ‘Cockiness.’ He also was the supporting act for her 2015 Diamonds World Tour, and they have accompanied one another to multiple industry events over the years.

They were first romantically linked in January 2020 when Rihanna split from her boyfriend of three years, billionaire businessman Hassan Jameel.

Flash forward to July 2020, they were seen flirting up a storm when the mogul asked Rocky to appear in her Vogue Fenty Skin campaign video.

They were also spotted holidaying together in Barbados around Christmas last year.

What is Rihanna’s net worth?

Forbes estimates that Rihanna’s net worth is US$1.7 billion (approx. $2.3 billion) — the bulk of which, around US$1.4 billion (approx. $1.9 billion), is thought to come from Fenty Beauty.

Founded in 2017 by Rihanna, the ANTI songstress is also the CEO of Fenty Beauty, and owns 50 per cent of the company.

A lot of her other earnings, in conjunction with her music and acting, also come from Savage x Fenty, her lingerie company understood to be worth US$270 million (approx. $364 million).

Does Rihanna have social media?

Yes — Rihanna has a Twitter account with over 102 million followers, an Instagram account with over 103 million followers, and an official Facebook page with over 101 million followers.

She also has a YouTube page with almost 38 million subscribers.