The Journey of Rihanna: 6 Key Moments in Her Music Career

Even before the advent of internet popularity, Robyn Fenty was already a household name in different corners of the world. However, many knew and only still know her by her middle appellation— Rihanna. With a voice that has commanded airwaves and a fashion sense that has graced runways, she has seamlessly woven her presence into the hallways of history.

The Barbados-born singer was discovered at age 15, with a unique voice type known as a mezzo-soprano, with a range of B2 to C6 at three octaves (Huffpost). Her crossover into the US music scene saw her being signed to a Jay-Z-led Def Jam Recordings. Although Rihanna’s rise to stardom was not a slow-paced one, her growth in the music scene was one for the records.

From being a high school dropout, she became a multiple Grammy Award-winning artist. She rose to be one of the best-selling female music artists of all time and became one of the female billionaires of the 21st century.

While it might appear that Rihanna was made for stardom, her journey is one of artistic innovation, fearless expression, and mastery of reinvention, highlighted by some key moments that marked the traction of her music career.

Some of these moments are:

1. The Release of “Pon de Replay”

Rihanna burst onto the music scene with her debut single, “Pon de Replay.” The story behind the song began in a hotel room in Barbados, when American Record producer, Evan Rogers, picked her out of her girl group trio after they had gone to audition for him. He got her signed to his production company—Syndicated Rhythm Productions, where she made the demo tape for “Pon de Replay”. 

Rogers then sent the tape to Def Jam Recordings, where it was played for Jay-Z, who initially felt the song was too big for the young girl. Rihanna ended up changing Jay-Z’s mind after she performed it for him live, and he instantly signed her to the label. Def Jam released the single in May 2005 as a summer bop, and it was an instant hit. “Pon de replay” charted successfully worldwide peaking at No. 2 on the US Billboard Hot 100 chart and the UK Singles Chart. The song which marked the beginning of her music career also became the hottest club song in the US, peaking at No. 1 on the Billboard Dance Club Songs.

2. Evolution with “Good Girl Gone Bad” (2007)

Rihanna’s third album, Good Girl Gone Bad, was a pivotal moment in her career. The album’s lead single, “Umbrella,” featuring Jay-Z, not only topped charts but also signaled a bold departure from her earlier image. Good Girl Gone Bad had songs with a more upbeat tempo that were different from her usual tune. The album had the most positive reviews from music critics out of her three albums at the time (Metacritic), with “Umbrella” topping the charts in 13 countries, and remaining in the No. 1 spot in the UK for 10 consecutive weeks.

The icing on the cake was the several awards and nominations it earned Rihanna, just two years into her music career. She and Jay-Z won a Grammy Award for Best Rap/Sung Collaboration at the 2008 Grammy Awards.

3. “Rated R” and “Rude Boy” (2009)

“Rated R” marked the incorporation of a darker and more foreboding tone into Rihanna’s music. This was her fourth studio album, released in November 2009, and it was a critical success. While the album had six commercially successful singles, “Rude Boy” became the biggest song on the album, by topping the US Billboard Hot 100 chart for five weeks and remaining in the top 10 position in over 20 countries in the world.

4. Collaborations and “Love The Way You Lie” (2010)

In 2010, for his seventh album, Recovery, rapper Eminem featured Rihanna on his single “Love The Way You Lie.” The song reflected a turning point in the usual Rihanna vocals, causing vocal critics to praise her versatility. The single achieved worldwide success when it topped the charts in over 20 countries and became the biggest-selling song of 2010 in the UK.  It was the first of her singles to sell over a million copies in the UK. 

Following her domestic violence episode with singer Chris Brown, the song garnered even more attention. The accompanying music video featured Dominic Monaghan and Megan Fox in an abusive relationship, while Eminem and Rihanna sang in front of a burning building.

5. “Anti” and Artistic Maturity (2016)

Anti, Rihanna’s eighth studio album, signified a departure from Rihanna’s previous works, embracing a more experimental and mature sound. It was released exclusively on Tidal, a music streaming service previously owned by Jay-Z. The whole album was a commercial success, and it peaked at No. 1 on the US Billboard Hot 200. 

The lead single, “Work” featured American rapper Drake. Critics praised the style of the song, as it indicated a return to her dancehall music style, while the accompanying video featured a sultry dance style that went viral. “Work” reached No. 1 on the US Billboard Hot 100 Chart, staying there for nine weeks.

6. Super Bowl LVII Performance (2023)

Rihanna was the headline performer at the 2023 Super Bowl halftime show, after several years of hiatus from the music scene. Her performance at halftime brought back fans and new Rihanna lovers as the performance reached over 121 million concurrent viewers and became the most-watched Super Bowl halftime show of all time. Following her performance and the announcement of her second pregnancy, social media went agog with videos of people in red overalls (Rihanna wore this for her performance), reenacting the iconic dance to her live performance of her chart-topping single, “Rude Boy”.

Rihanna’s journey and the climax of her music career have been interesting, given her background. These pivotal moments in her career have helped shape her success.

Photo by Kevin Winter/Getty Images