Rihanna’s Life Story: From Island Tomboy to Platinum Pop Sensation

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From singing into a hairbrush to selling millions of albums worldwide, Rihanna’s story is a mixed bag of strength, luck, and perseverance.

Now thriving as a fashion icon and music idol, she often refers to her childhood struggles as the driving force behind her many ventures. Her life wasn’t always about making headlines and performing concerts. On the contrary, Rihanna’s story begins on a small island with a drug-addicted father and a producer who didn’t think she could sing.

 

Growing up in a troubled home

Robyn Rihanna Fenty was born on February 20th in 1988, in Saint Michael Parish on the island of Barbados. She was the eldest child born to humble parents. Her mother worked as an accountant and her father was a warehouse supervisor.

Rihanna grew up in a small bungalow along with her two younger brothers. Money was always low throughout her childhood. Yet her father would come home drunk having spent half his paycheck on alcohol and crack. His addictions put tremendous strain on the family and his drug-induced tempers would often turn physical. While her mother was the primary target, on one occasion he turned on Rihanna after she asked to stay 10 more minutes at the beach.

When her father lost his job, everything got worse. Food became scarce, the house was littered with drug paraphernalia, and Rihanna would walk in on her father smoking crack. She closed herself off and would barely speak to anyone. It became so stressful that she suffered from intense headaches, which led to countless exams and the belief that she had a tumor.

At school, things weren’t much better. Rihanna was a bright student, particularly in math and chemistry, but her grades began to decline. She was constantly bullied over her light complexion – due to her father’s Irish descendence. But Rihanna had been toughened by her father’s behavior and would settle the tauntings with her fists.

At seven years old, Rihanna found an escape from her life’s chaos. She’d turn on the radio and sing into a hairbrush along with her idols Madonna, Mariah Carey, and Janet Jackson. During these short-lived moments of happiness, Rihanna felt like she belonged. She knew in her heart that her future was in music – although it seemed unlikely to happen while on the small island.

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A teen with a dream

At 14, her parents divorced and she was finally free from her crippling headaches. But now her mother had to work full-time, meaning Rihanna had to grow up fast. She helped make ends meet by working a cash register and selling clothes in a stall on the street.

Rihanna was now the primary caretaker of her youngest brother, but she also nurtured her love of music. She drew inspiration from reggae legend Bob Marley, who she considered an example to follow for aspiring artists in the Caribbean.

As time passed, Rihanna couldn’t shake the feeling that she could become a star if only the right person heard her sing. So she raised her chances by singing at the beach, at social gatherings, and at her high school talent show – which she won after singing Mariah Carey’s “Hero”.

Although becoming a singing sensation wasn’t her only aspiration at the time. Growing up with brothers also gave her the need to prove she was tough. She embraced a tomboy dress sense and became a cadet, rising to the rank of corporal. After years of bullying and witnessing her father’s abusive behavior, Rihanna refused to appear vulnerable to anyone – an attitude she upholds to this day.

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Young Rihanna with friend, Ella. / Image credit: Rihanna Instagram

First big break 

At 15, Rihanna formed a musical trio with her classmates. They performed at every possible venue, mostly covering songs by Destiny’s Child. One day, Rihanna’s friend revealed that her mother was acquainted with the record producer Evan Rogers, who just happened to be on holiday in Barbados with his wife. Rihanna jumped at the opportunity and asked her friend to set up an audition. The trio had no band name or formal training, but she couldn’t miss the chance to be heard.


Soon after, the group arrived at Evan Rogers’ hotel suite and waited nervously in the lobby. Rihanna fidgeted while deeply regretting her fashion choice of pink capris with a pink shirt. She hoped her makeup looked passable, considering her mother had never allowed her to wear makeup before.

Finally, the three girls were called in. As soon as Rihanna stepped inside, Evan was instantly taken by her Bajan beauty. Her fierce, green eyes and carefully applied makeup graced her with a presence that made him forget the two other girls existed. However, from experience, Evan suspected “the pretty one” of the group couldn’t sing.

He was wrong. The group performed two songs, and it was clear to Evan that Rihanna was meant for music. The audition ended, he thanked the girls and sent them on their way. It was unclear whether he would follow up or not, but Rihanna clung to the hope that he would.

Soon enough, Evan called and requested that Rihanna and her mother fly over to the United States for a demo recording. Rihanna was over the moon, and after a few visits, she gained her mother’s permission to move to Connecticut and live with Evan and his wife while she recorded her very first album.

You may never be good enough for everybody, but you will always be the best for somebody.

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Still from Rihanna’s Pon de Replay music video / Image credit: YouTube

The debut that topped the charts

Over the next year, 16-year-old Rihanna recorded four tracks, including a bubbly dancehall jam called “Pon de Replay“. The demo was sent out to various labels, one being Def Jam Recordings, where rapper Jay Z was just appointed as CEO. The rapper was impressed but considered the songs were ‘too big’ for the girl singing them. Nevertheless, Jay Z asked her to audition for him so he could see for himself.

Rihanna was now 17 and already on her way to audition for her first record label. She had spent the entire night choosing an outfit and was shaking at the thought of singing in front of Jay Z. Although the moment she began to sing Whitney Housten’s “For the Love of You”, Jay Z was sold. He could tell by the resolute look in her eyes that she was going to be a star – with or without him. So he asked her to sign with his label. They ended up staying until 3 am sifting through all the details of the contract. But Rihanna didn’t mind, her life-long dream was officially afoot.

Over the following month, Rihanna happily worked with various producers to complete her debut album. She chose her favorite track “Pon de Replay” as the lead single and in May 2005, it came second on the US Billboard and was among the top five hits worldwide. Rihanna was now on the map and quickly became a recognized name in the music industry.

Only eight months later, Rihanna released her second album A Girl Like Me, which launched two more hits. The track “SOS” became her first number one single and went Platinum. But before the glitz and glam of fame swept Rihanna away, Jay Z gave her a few words of advice which she still follows today,

Don’t change who you are, never forget where you came from, and always stay humble.

 

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Rihanna and Chris Brown attending the 2013 Grammy Awards. / Image credit: Getty Images

Good girl gone bad

At only 19 years old, Rihanna was topping the charts and living the dream. She continued to work with Jay Z and released the smash hit “Umbrella”, which won Rihanna her very first Grammy Award.

For her next albums, Rihanna assumed creative control and reinvented her music. As someone who quickly grows bored of the same things, she decided it was time to transform her cutesy image into something risque and sexy. Her music videos became more suggestive and controversial, but her fanbase grew along with her worldwide acclaim.

At 21 years old, her fame gained a different kind of attention. Rihanna began dating Chris Brown, a rapper from an equally turbulent childhood. The relationship was rocky, and on the night before her performance at the 51st Grammy Awards, Rihanna found suspicious texts on his phone. She promptly confronted him while they drove home, only to discover he had cheated on her with a former employee. The argument became heated and Chris threw the first punch. Rihanna, a tough woman with military training, fought back. It became a full-on battle inside the car, where she emerged severely cut and bruised – with marks of strangulation around her neck.

The traumatic event ensued in a media firestorm. But just like she did back in her teens, Rihanna put up her guard and refused to show herself as a vulnerable victim. Instead, she chose to use this experience as another step in her success story. Rihanna became a spokesperson and collaborated with artists such as Eminem and Kanye West in songs about domestic violence.

However, her familiarity with abusive men made it hard for her to leave the relationship completely. After the restraining order was reduced to enable a professional relationship, Rihanna became involved with Chris once again. Although it didn’t take long before she finally decided enough was enough and left him for good.

Sure, you wish you did some things differently. But there is no sense in becoming burdened with regret over things you have no power to change.

 

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Rihanna hosts the 2017 Diamond Ball to raise money for health and education initiatives in Malawi and the Caribbean. / Image credit: Taylor Hill/FilmMagic

Business ventures and influencing generations

Despite her young age, Rihanna’s dream of getting her music out into the world falls short of her current reality. Within a decade, she has become a best-selling songwriter, singer, and actress. She has sold over 540 million albums worldwide, won countless awards, and is the youngest solo artist to score 14 Billboard music hits. She has appeared in Hollywood blockbusters, named a major cultural influencer, and even has a national holiday under her name in Barbados.

But Rihanna has never been one to settle. She has also established herself as an edgy entrepreneur in the realms of fashion and beauty. Her latest business venture being her new cosmetic company Fenty Beauty, the first makeup line to offer a largely diverse variety of skin shades.

For all the wealth and fame she has gathered since her debut, Rihanna is eager to put her influence to good use. At only 18, she created Believe Foundation to help terminally ill children. From then on, she has funded countless charity ventures for causes ranging from cancer research to medical supplies for disaster victims. Former President Barack Obama has personally praised her work, stating “You’ve become a powerful force in the fight to give people dignity.”

With a headstrong character and a heart of gold, Rihanna is in a league of her own. She maintains a tenacious resolve to live her life on her own terms while helping others and inspiring upcoming generations to do more. Regardless of the bumps along the way, Rihanna is proud to say she always follows her heart, and encourages you to do the same.

When you follow the things that feel great to you, you can never lose.


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