The Real Life Rags-to-Riches Story of Rihanna Who Went From Selling Clothes on the Street to Winning 9 Grammy Awards

Pop icon Rihanna is a household name, and it would be difficult to find someone who hasn’t heard at least one of her hit songs. But not as many people know about the struggles she’s had to overcome in her life. While many celebrities were born into wealthy families, Rihanna had a less lavish upbringing. Despite the cards she was dealt at birth, the Barbadian singer triumphantly rose above all the challenges.

Rihanna was born in Barbados and had a difficult childhood.

Robyn Rihanna Fenty was born on February 20, 1988, in Saint Michael, Barbados to Monica and Ronald Fenty. Her mom was an accountant, while her dad worked as a warehouse supervisor. Rihanna grew up listening to Caribbean music genres, like reggae, as well as American R&B and hip-hop.

Despite her love for music, Rihanna had a difficult upbringing. Unlike some wealthy individuals who inherit their fortune, Rihanna’s success is a result of her own hard work and determination. She is a true self-made success story.

She’d often help her father sell clothes to make ends meet.

During Rihanna’s childhood, her father earned a living by selling clothes on the street or from his car. At times, Rihanna would join him, either by choice or necessity. Ronald Fenty, Rihanna’s dad, shared in a 2011 interview that she would set up a stand on the side of the street and sell hats, belts, and scarves.

She also had a sweet tooth for business, packaging candies to sell to her school friends for a profit. Her entrepreneurial spirit left a strong impression on her father, who predicted she would later pursue a career in business.

She had a tough relationship with her dad.

Rihanna’s relationship with her father has had its ups and downs. From a young age, there appeared to be a strong ambivalent undertone to their relationship. In 2009, Rihanna revealed that she had not been in contact with her father, Ronald, for 18 months.

However, in 2016, it seemed their relationship was improving when Rihanna purchased a mansion for him in Barbados. Despite their tumultuous relationship, it appears that Rihanna still cares for her father and wants to support him.

Rihanna’s musical talent was discovered when she was only 15 years old.

Back in 2003, Rihanna collaborated with 2 of her classmates to form a musical trio in her home country. Despite not having any name or material, the group auditioned for American record producer Evan Rogers. Rogers was immediately impressed with Rihanna’s talent. “The minute Rihanna walked into the room, it was like the other 2 girls didn’t exist.”

Subsequently, Rogers arranged a follow-up meeting with Rihanna and her mother, and then invited her to the United States to record some demo tapes that could be sent to record labels. In May 2005, Rihanna released her debut single, “Pon de Replay.” The single charted successfully worldwide, reaching the top 5 in 15 countries, including #2 on the US Billboard Hot 100 chart and the UK Singles Chart.

She quickly went on to become a successful singer, winning 9 Grammys.

Following the release of her first single and shortly after her debut album, Rihanna’s music career took off at a rapid pace. She received her first Grammy Award in 2007 for Best Rap/Sung Collaboration for “Umbrella,” which featured Jay-Z.

Rihanna then made her debut on the Grammy stage at the 50th Grammy Awards in 2008 with her performance of “Umbrella.” Throughout her career, she has been honored with a total of 9 Grammy Awards for her contributions to the music industry.

Currently, Rihanna is on a hiatus from music-making.

Throughout most of her career, the popular music icon consistently produced chart-topping hits. However, following what many consider to be her creative pinnacle with the release of her previous album, “Anti,” on January 28, 2016, Rihanna largely withdrew from the music scene, excluding the occasional appearance and performances of older hits.

She’s been focusing on building her business and being a mom.

However, while Rihanna was once focused on her music career, she has since shifted her focus toward the beauty and fashion industry. In 2017, she launched her Fenty Beauty line, followed by her Savage x Fenty lingerie brand in 2018. Through these successful ventures, the 35-year-old singer has become a billionaire.

Additionally, in January of last year, Rihanna announced that she was pregnant and eagerly anticipating her first child. On May 19, 2022, the renowned artist gave birth to her first baby with A$AP Rocky. As a result, motherhood became a top priority for her, and she expressed her enthusiasm, stating, “It’s legendary. It’s everything. You really don’t remember life before.”

She’s planning a big comeback and the release of a new album this year.

During the Super Bowl halftime show, Rihanna made a brief return to her music career. After being away from the stage for 7 years, the singer and entrepreneur performed a dozen hits, acknowledged her nonmusical ventures, and revealed that she was pregnant with her second child.

In February 2023, Rihanna revealed that she was in the process of working on a new album that she hopes to release this year, despite being pregnant with another child. “I want to play. And by play, I mean I have my ideas in my head, but I can’t say them out loud yet,” she said. “I just want to have fun. I just want to make music and make videos.”

Rihanna’s journey into motherhood took an adorable turn when her 10-month-old son humorously interrupted her workout session. The heartwarming video, which showcases the singer’s genuine moments with her baby boy, has garnered over 27 million views. Currently expecting her second child, Rihanna had previously announced her first pregnancy in January 2022 and gave birth in May. The star and her boyfriend, A$AP Rocky, are elated with their parenting roles, eagerly awaiting the arrival of their next bundle of joy.

Motherhood has brought both strength and challenges for Rihanna. While the joy of being a new mom has empowered her, balancing her illustrious career with parenting duties has been a struggle. The “Umbrella” singer candidly expressed the difficulty of juggling work and motherhood, emphasizing the importance of choosing projects that truly matter. Despite these challenges, Rihanna’s newfound confidence led her to perform at the Super Bowl halftime show, a testament to her resilience and adaptability.

Rihanna’s philanthropic endeavors have left an indelible mark on numerous global causes. From establishing the Believe Foundation at 18 to support children with terminal illnesses to her significant contributions through the Clara Lionel Foundation, Rihanna’s commitment to making a difference is evident. Her annual charity gala, The Diamond Ball, raises funds for her foundation, and her collaboration with various organizations and campaigns further amplifies her humanitarian efforts. Recognized for her continuous dedication, Rihanna has received accolades like the Peter J. Gomes Humanitarian Award, solidifying her legacy as a changemaker.