Rihanna's top 20 career-defining moments

After Rihanna’s demo caught the attention of teams at Def Jam, label CEO Jay-Z and record executive L.A. Reid set up an audition for her. The two were so impressed with her audition that they drew up a contract that night, and she became the label’s newest signee. 

In 2005, Rihanna released her debut album, Music of the Sun. She brought her Caribbean roots to her first single, “Pon De Replay,” and the song peaked at No. 2 on the Billboard Hot 100.

Just a year after releasing her debut album, Rihanna followed up with her sophomore project, A Girl Like Me. The lead single, “S.O.S.,” became Rihanna’s first No. 1 song on the Billboard Hot 100.

In 2007, Rihanna and Jay-Z released their hit single “Umbrella.” Co-written by The-Dream, "Umbrella" became RiRi’s second No. 1 hit and earned the singer her first Grammy Award for Best Rap/Sung Collaboration. 

By the time Rihanna released her third album, Good Girl Gone Bad, she was ready to enter a new era. She departed from her Caribbean sound that was heard on her previous albums and played into more pop and R&B. Not to mention, she was going for a more mature and edgier look to her image. Some of the album's hit songs included "Umbrella," "Don't Stop The Music," and "Take a Bow." 

In 2010, Rihanna released her fifth album, Loud. The album garnered seven singles, including “Only Girl (In the World),” “What’s My Name?,” and “S&M.” The album helped Rihanna land her first Album of the Year nomination at the Grammy Awards.

By 2013, the American Music Awards had established Rihanna with a coveted title: its first-ever Icon Award. After she performed her song “Diamonds,” Rihanna’s mother, Monica Fenty, presented her with the award. In her acceptance speech, she stated, “I can’t believe that at 25 years old, I’m holding an Icon Award. If you know me, then you know that I love you. I am grateful.” 

Rihanna has always been known for making fashion statements, and different brands took notice. In 2014, Puma brought her on as Creative Director to oversee women’s apparel, focusing on fitness and training. Rihanna’s tenure with Puma ran from 2014 to 2018. 

Rihanna knows how to set trends for people to follow, and CFDA wanted to award her for pushing fashion forward. She adorned herself in a custom Adam Selman dress as the CFDA presented her with the Fashion Icon Award. In her acceptance speech, she said, “I grew up on a really small island, and I didn’t have a lot of access to fashion. But as far as I could remember, fashion has always been like a defense mechanism, even as a child, I remember thinking, ‘She can be beat me, but she can not beat my outfit.’”

In 2015, the theme for the Met Gala was "China: Through the Looking Glass." Rihanna’s look was designed by Guo Pei and included a yellow fur-trimmed gown with a show-stopping cape and gold headpiece. The look became a favorite of the night and helped Rihanna’s status as a Met Gala darling.  

In 2016, Rihanna released her eighth album — what most people deem her magnum opus — Anti. With production from the likes of Boi-1da, DJ Mustard, Hit-Boy, and more, the album included four singles, including “Kiss It Better," "Love on the Brain," and the Drake-assisted track “Work.” 

Rihanna was ten years into her career when MTV honored her with the Michael Jackson Video Vanguard Award. While recipients typically perform a 15-minute medley, Rihanna did something different. She performed four times throughout the award ceremony, including hit tracks “We Found Love” and “Better Have My Money.” 

Throughout her career, Rihanna has been a philanthropist working to highlight health and education in her home country of Barbados. She founded the BELIEVE Foundation and the Clara Lionel Foundation, which was named after her grandparents. Her charitable work hasn’t gone unnoticed, as the Harvard Foundation for Intercultural and Race Relations presented her with the 2017 Harvard Humanitarian of the Year award. 

In 2017, Rihanna stepped into the cosmetics world with the launch of Fenty Beauty. With her makeup line, the singer was adamant about creating products that were inclusive to all skin tones, which included 40 foundation shades. Rihanna knew that the lack of representation was all too common in the cosmetics industry, and her mission was to change that. With Fenty Beauty making products that appeal to everyone, the brand has given the beauty industry a run for its money. 

Rihanna is known for her show-stopping looks at the annual Met Gala. In 2018, the theme of the night was "Heavenly Bodies: Fashion and the Catholic Imagination." Naturally, Rihanna won the night since she dressed up as the pope with a high-fashion twist. The look was designed by Margiela, making it the first time Rihanna wore the designer to the Met Gala. 

As a woman who’s always pursuing her next business venture, just a year after launching her beauty line, Rihanna launched her lingerie line, Savage x Fenty. Not only did she hold the brand’s first fashion show during 2018 New York Fashion Week, but she also held fashion shows that were available to view on Amazon Prime. Like her beauty brand, her mission with Savage x Fenty was to bring more diversity and inclusivity of all shapes and sizes. 

In 2020, Rihanna added to her beauty brand with her first skincare line, properly named Fenty Skin. At the time of its release, the line included a cleanser, toner, and sunscreen. Since then, she’s expanded the line to include facial masks, body creams, and more. 

Fans were shocked and excited to hear that Rihanna was headlining the Super Bowl LVII halftime show. It had been five years since she performed live at the 2018 Grammys, so it gave fans hope that new music would finally be on the way. While fans still await new music, Rihanna also shocked everyone by revealing her second pregnancy while performing. 

Since the release of her 2016 album Anti, Rihanna has been pretty quiet on the music front, besides a handful of features. In 2022, she returned with “Lift Me Up,” the lead single from the superhero film Black Panther: Wakanda Forever. Produced by Ludwig Goransson, the song was nominated for an Academy Award and a Golden Globe. 

“B—h Better Have My Money” is a catchy song and a mantra to Rihanna's life. In 2021, Rihanna was welcomed into the billionaire club. Not only did her reported billionaire status make her the world’s wealthiest female musician, but she ranks second behind Oprah Winfrey as the wealthiest female entertainer. While Rihanna’s music career helped her status, it was the fortune from her business ventures, particularly Fenty Beauty and Savage x Fenty, that pushed her to the top.