Before she was a billionaire mogul, a beauty empire boss, and mom, Rihanna was a girl from Barbados with a dream — and a voice that would change the industry. She stepped onto the scene at just 17 years old with her debut single “Pon de Replay,” and since then, she’s given us chart-topping albums, endless iconic eras, and a legacy of fashion and energy that shifted the culture. After her mega-success as an artist, she expanded her empire (and family with A$AP Rocky) into Savage X Fenty, Fenty Beauty, Fenty Skin, and Fenty Hair. So, in honor of how far she has come, we’re throwing it back to a few classic Rihanna moments — from her childhood in Barbados to “TRL,” early awards show glams, and more.
1. A childhood moment in Barbados with family
This nostalgic photo captures a young Rihanna with her younger brother, Rorrey Fenty. He posted it with the caption, “La Família!” and the disclaimer that their other brother wasn’t born yet. It was a sweet moment, reflecting Rihanna's humble beginnings.
2. Sibling love at the People Music Lounge
Back in 2007, Rihanna stepped out in New York City with her younger brother to go to the People Music Lounge. The duo's close bond was evident as they enjoyed the event together, showcasing Rihanna's commitment to family amidst her rising fame.
3. Posing with her mother and grandfather at the TIME 100 Gala
At the 2012 TIME 100 Gala, Rihanna was accompanied by her mother, Monica Fenty, and grandfather, Lionel Brathwaite. Celebrating her recognition as one of the world's most influential people, this appearance highlighted the strong family support behind her success.
4. Joining the "SOS" BET Telethon Relief event
On Sept. 9, 2005, Rihanna participated in the BET Telethon Relief event at CBS Studios in New York City. The event aimed to support Hurricane Katrina victims, and Rihanna's involvement demonstrated her early commitment to humanitarian causes.
5. Backstage at the 2005 World Music Awards with industry icons
As just a teenager, Rih was already rubbing shoulders with icons. Backstage at the 2005 World Music Awards, she linked up with Babyface, Destiny’s Child, Usher, and Teairra Mari for a photo. That same night, she joined a tribute performance honoring Destiny’s Child. This gathering of music industry heavyweights highlighted the significant support and mentorship she received early in her career.
6. Pulling up to “TRL” in peak 2000s fashion
Rihanna made one of her first appearances at MTV’s “TRL” studios in Times Square on Sept. 6, 2005. It was a rite of passage for every pop star of the era — and she understood the assignment.
7. Being lifted like a queen in Copenhagen
During the 2006 MTV European Music Awards in Copenhagen, Denmark, Rihanna delivered an energetic performance, even being carried by dancers on stage. Her star power was already in full force by the time she stepped on the international stage.
8. Showing love as L.A. Reid receives his music visionary award in NYC
Rihanna attended and performed at the ceremony where L.A. Reid received the UJA-Federation of New York's Music Visionary Award. It was an important moment for both of their careers, showcasing new milestones they’ve reached as artists.
9. Gracing the red carpet at New York Fall Fashion Week
Rihanna attended the Conde Nast Media Group's 3rd Annual Fashion Rocks Concert at Radio City Music Hall in New York City. Her elegant appearance on the red carpet showcased her growing influence in both the music and fashion industries.
10. Rockstar energy at the 2009 American Music Awards
With a mohawk and metallics, Rihanna posed for portraits at the 2009 American Music Awards. This was the peak of her Rated R era, and she made sure we never forgot it.
11. Filming the “What's My Name" music video in NYC
Rihanna was spotted filming the music video for her hit single "What's My Name" featuring Drake in the Lower East Side of Manhattan in September 2010. Her red hair, big smile, and off-duty looks were giving carefree icon.
12. The “Loud Tour” energy in Oakland
Rihanna lit up the Oracle Arena in Oakland, CA, during her “Loud Tour” on June 30, 2011. The looks, the vocals, the energy — we can always count on her for an amazing show.
13. That first Grammy glow
She won her very first Grammy Award in 2008 for “Umbrella” featuring JAY-Z, and the photo says it all. Rihanna’s joy in this backstage pic at the Staples Center is forever iconic. This accolade marked a significant milestone in her musical journey.