Rihanna's debut album, Music of the Sun, was released on August 30, 2005 in the United States, yielding two singles, the first being "Pon de Replay" which was released on August 22, 2005. This single became a huge success upon its release peaking at number 2 in the US on Billboard Hot 100 charts. It also became a global hit where it peaked within the top 10 across 15 countries as well as achieving top 20 chartings on 20 charts around the world. The single written by Carl Sturken and Evan Rogers was described by Rolling Stone magazine as a "poppy piece of dancehall reggae with slapping, syncopated beats recalling big-band jazz." However, despite "Pon de Replay"'s commercial chart success, the album itself was rated 2.5 out of 5 stars by Rolling Stone Magazine and described as lacking the replay value, ingenuity and rhythm of the single with "generic vocal hiccups and frills" of US R&B inflecting upon her "caribbean charm". Since its release, the album reached the top 10 in both US and Canadian charts, gaining gold certification from the RIAA from selling 500,000 units and subsequent platinum certifications for selling 2 million units in various other countries.

The second single "If It's Lovin' That You Want" was less successful than "Pon de Replay", but it became a hit nonetheless by managing to achieve a top 40 charting in the USA reaching a high of number 36. In Australia, Ireland and New Zealand the single proved to be well-received reaching the top 10 in those countries. Overall the single became a top 40 hit on 11 charts around the globe. Despite the album not having huge promotion and only releasing two singles Music of the Sun managed to sell over 500,000 copies in the United States and 2 million worldwide.

Rihanna second album, A Girl Like Me, was released in April 2006; less than eight months after the release of her first album. The lead single, "SOS", was used in an endorsement deal with Nike. The song became Rihanna's first number-one on the Billboard Hot 100 chart; it also debuted at number one on the Hot Digital Songs chart. "SOS" peaked at number one in Australia and number two in the UK. The second single, entitled "Unfaithful", was written by R&B singer Ne-Yo. The song became her third top ten hit in the U.S. and in the UK. The third single, "We Ride", was not as successful as her previous releases, failing to chart on the U.S. Billboard Hot 100, however, it became her fifth UK top 20 single, where it peaked at number 17 on that chart and peaked at number one on the U.S. Hot Dance Club Play chart. Rihanna's fourth single from the album, "Break It Off" featuring Sean Paul, had already climbed to number 45 on the Billboard Hot 100 based solely on airplay. It was released as a digital download on February 19, 2007, which made the song jump from number fifty-two to number ten and then eventually peak at number nine. A Girl like Me's sales were significantly stronger, selling over 1 million in the U.S.

In total, Rihanna has had eleven number-ones on the Billboard charts and has had major success on the Hot Dance Club Play chart with eight number-ones. When Rihanna received an endorsement deal from Clinique, she recorded a song written by Ne-Yo entitled "Just Be Happy" as part of the deal to promote their Happy fragrance. Rihanna also recorded a song called "Winning Women" with Pussycat Doll Nicole Scherzinger for P&G’s female deodorant Secret.

During this time Rihanna also made her acting debut in a cameo role in Bring It On: All or Nothing, which was released on August 8, 2006.

Rihanna went into the studio in early 2007 with Ne-Yo, Stargate, and Timbaland among others to record her third album, Good Girl Gone Bad. The album was released on June 5, 2007, features Jay-Z and Ne-Yo. Rihanna worked with Timbaland on three songs in the album---"Lemme Get That", "Rehab" and the Japanese bonus track "Haunted". Justin Timberlake co-wrote and provides background vocals on "Rehab".

The album so far has yielded eight hit singles, including the world-wide number one hit "Umbrella", featuring Jay-Z. In addition to reaching number one in various countries, "Umbrella" was the number one single in the UK for 10 consecutive weeks, making it the longest running UK number one single since Wet Wet Wet's single "Love Is All Around", back in 1994, and the longest running number one by a female artist since Whitney Houston's "I Will Always Love You", which also topped the chart for 10 weeks in 1992. By the end of the year, "Umbrella" was ranked second on the Billboard Hot 100 year-end chart in the United States.

Her other singles, "Shut Up and Drive" and "Don't Stop The Music" were able to mirror the success of "Umbrella", with "Don't Stop the Music" reaching number three on the Billboard Hot 100, becoming Rihanna's seventh top ten single and her fourth top five hit, while peaking at number one in various countries. The fourth single (third single in the US and UK) "Hate That I Love You", featuring Ne-Yo, was able to peak at number seven in the U.S.

Starting September 12, 2007, Rihanna toured Canada and the United States in support of the album with several shows and then crossed to Europe. The tour was called called the Good Girl Gone Bad Tour, and was released on DVD on June 17, 2008, featuring the show performed at the Manchester Evening News Arena on December 6, 2007.

With the re-issue of her third album, titled Good Girl Gone Bad: Reloaded, which was released on June 17, 2008, Rihanna released the singles "Take a Bow" — which became a worldwide number-one hit —, the duet with Maroon 5, "If I Never See Your Face Again," and "Disturbia", the latter of which also peaked at the number-one spot on the Hot 100 chart, giving the artist her fourth number-one singles and her ninth top ten hit in the U.S. The song "Rehab," which features Justin Timberlake, was later sent radio stations on October 7, 2008 and has so far peaked at 34 on the Billboard Hot 100.

Good Girl Gone Bad has so far sold 6.2 million copies worldwide and has gone 2x Platinum in the US, 4x Platinum in the UK and Canada, 5x Platinum in Russia, and 6x Platinum in Ireland; including Good Girl Gone Bad: Reloaded.

Rihanna is confirmed to appear as a guest act for the Royal Variety Performance 2008, which will be staged at the London Palladium on Thursday 11th December.

On November 23, 2008 Rihanna was nominated for two American Music Award (Favorite Pop/Rock Female Artist and Favorite Soul/R&B Female Artist). Rihanna won in in both categories making it her third AMA. Rihanna alaso performed "Rehab" on stage at the AMA.

Rihanna was also selected as the spokesmodel for Gucci’s first UNICEF ad campaign. She will appear in the fashion house’s Tattoo Heart campaign, premiering in December. Rihanna will be photographed in series of special edition print ads with UNICEF items, twenty-five percent of sales will benefit the children’s charity.

In New York, Rihanna was then enlisted by Gucci's Frida Giannini along with Madonna to light the UNICEF Christmas snowflake. Rihanna, dressed head to toe in Gucci, is now the face of the fourth annual Gucci Campaign to Benefit UNICEF, which aims to raise funds for children in Africa through the sale of it's Tattoo Heart collection of bags.