From Barbados to the Grammys: The Evolution of Rihanna


| LAST UPDATE 09/11/2023

By Benedict Swirsky

From an island girl to a Grammy winner to a successful businesswoman, Rihanna's evolution is inspiring. Let's go back to the beginning and look at how Rihanna became one of the world's biggest celebrities.

Barbados Girl

While the world simply knows her by her middle name, there is much more to Rihanna than meets the eye. She was born Robyn Rihanna Fenty on the island of Barbados in 1988 and was destined to become a star.

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@badgalriri via Instagram

She was born to Monica and Ronald Fenty and has two brothers, two half-sisters, and one half-brother. Her childhood wasn't exactly picture-perfect. She struggled with chronic migraines and problems at home. Her parents ended up divorcing when she was 14. In one more year, her life would change entirely.

The Big Audition

Rihanna formed a band with two of her classmates. They didn't even have a band name or an original song. Still, they landed a once-in-a-lifetime opportunity to audition for record producer Evan Rogers while he was visiting Barbados. Rogers worked with stars like Christina Aguilera and American Idol winner Kelly Clarkson.

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@badgalriri via Instagram

Rogers knew there was something different about her. According to Entertainment Weekly, he said, "The minute Rihanna walked into the room, it was like the other two girls didn't exist. She carried herself like a star even when she was 15. But the killer was when she opened her mouth to sing."

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"Come, Mr. DJ"

After her epic audition, Rogers invited Rihanna to the United States so she could record a demo tape. Rihanna and her mother traveled back and forth for a year until she eventually moved in with Rogers and his wife to make her dream happen. Rihanna said about leaving her home, "When I left Barbados, I didn't look back."

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Marion Curtis/Starpix via Shutterstock

Her completed tape was sent to Def Jam Recordings, and none other than Jay-Z listened to it. Intrigued by her sound, the rapper invited Rihanna to the office. She made her way to New York City and performed for the executives at Def Jam. Rihanna left New York City that day with a record deal.

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Meet Rihanna

A few months of recording and completing her album went by. Then, the world was finally introduced to Rihanna when her first single, Pon De Replay, was released in May 2005. The song was a smash hit around the world. The girl with a big dream from Barbados was being heard on radios everywhere.

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Matt Baron/BEI via Shutterstock

Her first album, Music of the Sun, was released in August 2005 and debuted on the Billboard 200 at Number 10. It looks like Jay-Z made the right decision. It was apparent that Rihanna had talent and something special, but would she be able to follow it up? Spoiler alert. She did.

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More Music

Rihanna kept coming out with winner after winner. Only a month after the release of Music of the Sun, she got right back into the recording studio to work on her second album. A Girl Like Me, Rihanna's sophomore studio album, went on the airwaves less than a year later. It featured songs like SOS, Unfaithful, and Break It Off. 

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Henry Lamb/BEI via Shutterstock

The hard work didn't stop there. Rihanna returned to the studio and began working on her third album. Good Girl Gone Bad made Rihanna a household name, and it won the artist her first Grammy award for her song, Umbrella. Other tracks off that album include Don't Stop the Music, Shut Up and Drive, and Hate That I Love You

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In Love

Rihanna had been friends with R&B singer Chris Brown since they were teenagers. Then, around February 2008, the pair started to get closer. They sang together at Z100's Jingle Ball, and Brown made a remix to her hit song, Umbrella. Brown also serenaded the Barbados singer with Happy Birthday at her 20th birthday party.

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Christopher Polk/Staff via Getty Images

While Rihanna and Brown initially denied romance rumors, insisting they were "just friends," they eventually emerged as a couple. Brown even visited her hometown with her! They were the hottest item in the music industry, both at the top of their game. However, things took a turn for the worse.

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A Canceled Performance

The couple was scheduled to perform together at the Grammys in February 2009. However, they were both no-shows, and their performance was canceled. Earlier that day, Rihanna called 911 and called Brown her attacker. Per People, Brown was booked on "felony criminal threats charges."

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Guignebourg-Nebinger-Orban-Taamallah/ABACA via Shutterstock

A source told People, "They've been fighting a lot lately. Lots of ups and downs. One second they're all lovey-dovey and then they're fighting like crazy." Brown pleaded guilty that June and served five years of probation. The couple briefly reunited in 2012, but it wasn't a long-lasting reunion. 

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Transforming Her Sound

Rihanna remained hard at work on her next album, and fans didn't have to wait long. She released her fourth studio album, Rated R, in November 2009. Rihanna worked with Timbaland and Ne-Yo on writing the lyrics for the album, which produced hit singles including Rude Boy and Te Amo

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Greg Allen via Shutterstock

Rolling Stone wrote about the album and Rihanna that she "transformed her sound and made one of the best pop records of the year." Critics from all over the world applauded her efforts. It was clear that Rihanna's success wasn't a fluke. The Barbados singer was here to stay.

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Dating Around

While her career was taking off, what was happening with Rihanna's love life? There was also a lot happening in that area. The Umbrella singer was seen out with Miami Marlins player Matt Kemp. However, a source told Us Weekly then, "It was never as serious as it looked."

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Kevork Djansezian/Staff via Getty Images

Titanic actor Leonardo DiCaprio and Shooter actor Ryan Phillippe were also reportedly flings of Rihanna. However, none of these rumored romances ever turned into something serious. Meanwhile, throughout this entire time, Rihanna was still working hard at producing more music.

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Let's Get "Loud"

In yet another quick turnaround, Rihanna released her fifth studio album, Loud, only a year after Rated R in November 2010. The album had international hits like Only Girl (In the World)What's My Name?, and S&M. She went on her third world tour at that point for the album and went on to smash records.

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Mark Sumner via Shutterstock

The tour included 98 shows across North America, Europe, and South America. It was one of the highest-grossing tours at that time. She also broke a record for the most sold-out shows for a female artist at the famous O2 Arena in London. Rihanna sold out ten nights!

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Everyone Wants To Work With RiRi

Being one of the most successful and talented artists has its perks. Everybody wants to work with you, and Rihanna had many major players in the industry who sought her out. Not only were her albums some of the biggest hits, but it seemed that every track she worked on was bound to be a success.

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Peter Brooker via Shutterstock

She collaborated with rapper Eminem on the song, Love the Way You Lie, which became an instant chart-topper. She also worked with Kanye West on All of the Lights. It doesn't stop there. She also worked with music legends like T.I., David Guetta, and Nicki Minaj.

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"Please Don't Stop the Music"

In November 2011, fans were treated to Rihanna's sixth album, Talk That Talk. Not only does bad gal RiRi talk the talk, but she also walks the walk. This album was another astounding success. Her single, We Found Love, was charting in the top ten for ten non-consecutive weeks. 

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David Fisher via Shutterstock

There is no stopping the music for Rihanna. A year after the release of Talk That Talk, she dropped her seventh studio album, Unapologetic. Her top-charting singles off that album include Diamonds and Stay. If only things could "stay" like this forever.

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A Shakeup

It seemed that a major shakeup was in order for the Disturbia singer. In May 2014, Rihanna announced that she left Def Jam Recordings, her longtime music label. She signed with Jay-Z in his new venture, Roc Nation. Now she was fully managed and represented by the company.

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Curtis Means via Shutterstock

She also began dipping her toes into the cinematic side of the entertainment industry. While this wasn't her first venture into acting because way back in the day, she had a minor role in Bring It On: All Or Nothing. Rihanna landed a role in Seth Rogen's This Is The End and voiced Tip in the movie Home. 

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Professing His Love

Rihanna captured the hearts of people around the world, including a certain Canadian rapper and singer. The pair first met on the set of her Pon De Replay music video. Rumors of their romance have sparked over the years, but it wasn't until 2016 that things seemed to be taking a more serious turn.

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Stephen Lovekin via Shutterstock

Drake presented Rihanna with the Michael Jackson Video Vanguard Award at the 2016 MTV Video Music Awards and professed his love. He said, "She's someone I've been in love with since I was 22 years old. She's one of my best friends in the world." They even got matching shark tattoos but ultimately broke things off.

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The Last Album

While fans didn't know it at the time, but the release of Rihanna's eighth studio album would be her last for the time being. Anti dropped in January 2016. It was an instant hit, peaking at Number 1 on the Billboard 200. She embarked on a world tour, performing around North America and Europe. 

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Ibl via Shutterstock

The top single off the album was Work with her on-and-off beau, Drake. More singles off the album included Needed Me and Love on the Brain. She appeared on several other artists' tracks, likeKendrick Lamar's Loyalty and DJ Khaled's Wild Thoughts, before her hiatus from music-making began.

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Fenty Beauty Launches

When she was only 29 years old, Rihanna launched her cosmetics brand, Fenty Beauty. Named after her own last name, the brand was a complete game changer. Fenty Beauty became available in September 2017 and offered foundations, highlighters, lip glosses, and more.

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Vogue via YouTube

The brand was applauded for its wide range of shades offered. Time Magazine named it one of "The 25 Best Inventions of 2017." That's high praise for the Barbados native. Since then, Fenty Beauty has influenced makeup everywhere. More and more brands are adding shades to their lines, which has been called the "Fenty effect."

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Acting It Out

In addition to starting a business, Rihanna kept working on her acting career. She had a recurring part on the fifth season of the A&E show, The Bates Motel. She also had a role in the sci-fi flick Valerian and the City of a Thousand Planets. What can't she do?!

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Warner Bros/Moviestore via Shutterstock

The answer is nothing. RiRi also sported dreadlocks for the film Ocean's 8. She portrayed Nine Ball, a computer hacker with some serious skills. She starred alongside Hollywood starlets Sandra Bullock, Cate Blanchett, and Sarah Paulson. Now that's a girl group for the history books.

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Trying To Find Love

Bad gal RiRi was looking to find love, and that's something everyone can relate to. It seemed like she had found it, too. She had been dating Saudi Arabian businessman and billionaire Hassan Jameel. When interviewed by actress Sarah Paulson for Interview magazine, Paulson asked her, "Are you in love?"

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David Fisher via Shutterstock

To which Rihanna responded with, "Of course I am." The couple began dating sometime in 2017 and were going strong. But love wasn't written in the stars for them. They ended things in 2020. A source told People, "Their lives were too different and it was hard to maintain a relationship."

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Keeping Busy

Nothing would be able to slow her down, though. Rihanna was busy with ten million other things. She had her lingerie brand, Savage X Fenty, which has become an iconic fashion name in the industry. She has collaborated with Amazon Prime Video on the Savage X Fenty fashion shows for years.

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Kevin Mazur/Contributor via Getty Images

She also released a skincare brand called Fenty Skin. RiRi did put a pause on her Fenty luxury clothing brand due to the COVID-19 pandemic. However, Fenty Beauty and Savage X Fenty have continued to expand. There were so many things that the singer was working on, but none of it was music, much to her fans' dismay.

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A New Boo

Rumors of romance began to swirl around Rihanna and longtime friend A$AP Rocky when they were photographed together on the red carpet for the 2019 British Fashion Awards. The two knew each other for years before, even performing together at the 2012 MTV Video Music Awards show.

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Matt Baron via Shutterstock

After the Fashion Awards, the pair were spotted together constantly. From vacationing in Barbados over Christmas to having dinner together in Los Angeles, they became the hottest couple in music. A$AP modeled for Rihanna's Fenty skincare line. That's a supportive boyfriend!

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She Found Love

If there were any doubts before, there shouldn't be any after this interview. A$AP Rocky told GQ that Rihanna is "the love of my life; my lady." He also said, "I think when you know, you know. She's the One." Finally, after all these years, Rihanna found love in a hopeless place.

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Matt Baron via Shutterstock

The couple continued to show their love for one another. They appeared at the 2021 Met Gala in coordinating outfits. RiRi was spotted supporting her man as he performed at the Rolling Loud Music Festival, and they went for a romantic dinner date afterward. Rihanna and Rocky were simply in love!

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Baby Bump

The old nursery rhyme goes, "First comes love. Then comes marriage. Then comes baby. In a baby carriage!" And that was exactly the next step for music's favorite couple. In a photoshoot with A$AP Rocky in New York City, Rihanna debuted her pregnancy.

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J M HAEDRICH/SIPA via Shutterstock

Rihanna wore a pink jacket, unbuttoned to show off her belly. Pregnancy didn't slow the Fenty owner down. She attended Paris Fashion Week and was out promoting her business. The couple welcomed their baby boy into the world in May 2022. According to records obtained by PEOPLE, his name is RZA Athelston. 

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Being a Mom

Being a mom is now another thing on Rihanna's extensive and impressive resume. She's already got singer, Grammy Award winner, business owner, and actress on there. But how was the star handling her new role? She opened up about motherhood to British Vogue, saying, "Oh, my God, it's legendary."

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@badgalriri via Instagram

She continued, "Essentially, from one person I became two. You walk into the hospital as a couple and leave as a family of three. It's nuts. And oh, my gosh, those first days are insane. You don't sleep. At all. Not even if you wanted to. We came home, cold turkey, had no one. It was just us as parents and our baby."

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Rihanna made an announcement that made fans everywhere freak out. In September 2022, Rihanna and the NFL announced that the Barbados native would perform at the Super Bowl Halftime Show. This would mark the first time in seven years that the We Found Love singer would perform.

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@badgalriri via Instagram

In a press conference, the singer said, "The Super Bowl is one of the biggest stages in the world. As scary as that was, because I haven’t been on stage in seven years, there’s something exhilarating about the challenge of it all." The savvy businesswoman also dropped merch to signify the special event.

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Making a Comeback

While it wasn’t a complete return to music, fans were excited to get a new track from the singer. Rihanna dropped the song Lift Me Up. This marked the first release since her 2016 album Anti. The track was featured in the movie Black Panther: Wakanda Forever, a sequel to the Marvel hit Black Panther.

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John Salangsang via Shutterstock

The song is a tribute to the late Chadwick Boseman, who played T'Challa, aka the Black Panther. Boseman passed away after a battle with cancer. Rihanna's moving tribute earned her her first Academy Award nomination. She performed the song during the 95th Academy Awards ceremony.

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A Big Debut

On Sunday, February 12, 2023, Rihanna made her much-anticipated return to the stage. It was halfway through the big match. The Philadelphia Eagles were up against the Kansas City Chiefs at the State Farm Stadium in Glendale, Arizona. The lights went dark, and Rihanna appeared on a floating stage dressed in all red.

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John Angelillo/UPI via Shutterstock

She was also sporting something else - a baby bump! Not only did Rihanna mark her first live performance in years, but she debuted the baby bump of her second child with A$AP Rocky. The internet went wild. Her halftime show became one of the most-watched shows in history, with over 121 million viewers.

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Bumping It Up

Since debuting her bump, Rihanna has excitedly been showing it off. She has been going about town as usual, attending the Oscars and the Met Gala. She flew to Paris to attend Paris Fashion Week and support her friend Pharrell in his new role as creative director for Louis Vuitton.

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Robert Gauthier/Contributor via Getty Images

Not only did she go to support his fashion show, but RiRi also modeled for Pharrell, showing off her baby bump in ads for Louis Vuitton. There is still no word on when her due date is meant to be, but the world will be waiting to meet Rihanna and Rocky's second bundle of joy.

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Where’s the Music?

There is still no word about Rihanna getting back into the studio. Although fans have tried asking and literally begging her to release a ninth album, they are still left waiting. Due to her Super Bowl performance, rumors were circling about a possible return to touring.

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Frank Micelotta/Picturegroup via Shutterstock

Yahoo wrote that Hits Daily Double reported that Rihanna is due to embark on a 2023 stadium tour. However, there has still been no word if this is actually happening or not from the Grammy winner herself. Being a mom and business owner is most likely keeping her busy enough.

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Rihanna Day

Although she left home years ago to pursue her dreams, Barbados still holds a special place in RiRi's heart. She once said, "This is still the place I call home. I love Barbados." The feeling is mutual. Her home country gave her the title of Ambassador for Culture and Youth in Barbados. They also declared her a national hero.

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@badgalriri via Instagram

Every year citizens celebrate Rihanna Day. Barbados also renamed a street to Rihanna Drive. During the renaming ceremony, the SOS singer said, "My whole life was shaped on this very road. I was just a little island girl riding bikes, running around barefoot and flying kites in the cemetery, but I had big dreams."

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What’s Next?

So what is next for Rihanna? She's a Grammy Award-winning singer, a business owner, an actress, a mother, and more. Her resume is never-ending and ever-impressive. Will she continue to expand her Fenty empire? Or will she opt for a quieter life now that she's a mother? Is a return to music happening? It might just be…

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@badgalriri via Instagram

Rihanna revealed to British Vogue that she's been recording all these years and said the following about releasing a new album, "I want it to be this year. Like, honestly, it’d be ridiculous if it’s not this year. But I just want to have fun. I just want to make music and make videos.” 

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Mom of Two

Fast forward to just a few months later, the stork has a happy announcement to make: Bad Gal RiRi is a mom of two! The Love on the Brain singer gave birth to her second son on August 1, 2023. According to his birth certificate, which was obtained by TMZ, the Fenty creator named her baby boy Riot Rose Mayers. 

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@badgalriri via Instagram

Although there's still no official word from Rihanna, sources told People that the Barbados native "feels her family is now complete." Every one of her family members' names begins with an "R" - even A$AP, whose legal is Rakim Athelaston Mayers. Talk about a special family tradition. Cheers to the happy parents! 

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