1988
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February 20
Welcome, Robyn Rihanna
Monica, an accountant, and Ronald, a warehouse supervisor, welcome daughter Robyn Rihanna Fenton. Her childhood on the Caribbean island of Barbados is deeply affected by her father's addiction to crack cocaine and parent's rocky marriage, which ends when she's 14. The shy kid finds an outlet through singing.
- 2003
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December
A Barbados Discovery
After forming a girl group with two classmates, Rihanna, 15, auditions for veteran producer Evan Rogers, who tells Entertainment Weekly, "The minute Rihanna walked into the room, it was like the other two girls didn't exist." She eventually moves to Connecticut to live with Rogers and his wife, while cutting a four-song demo. "When I left Barbados, I didn't look back," Rihanna adds. "I wanted to do what I had to do, even it meant moving to America."
- 2004
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Auditioning for Jay-Z
Rihanna's demo makes its way to Def Jam and the budding star is invited to audition for rapper turned Def Jam president Shawn "Jay-Z" Carter. "I was in the lobby just shaking," Rihanna, who sings Whitney Houston's "For the Love of You," tells Rolling Stone. "I signed her in one day," Jay-Z adds. "It took me two minutes to see she was a star."
- 2005
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August 30
Rihanna's Debut
Rihanna releases her first single, "Pon de Replay," kicking off her debut album, Music of the Sun, and it peaks at No. 2 on Billboard's Hot 100. The Barbados beauty tours with Gwen Stefani to promote her album, which sells more than 2 million copies worldwide. Rolling Stone calls the album "a seductive mix of big-voiced R&B and souped-up island riddims – what Beyoncé might have sounded like if she had grown up in the West Indies and skipped the whole Destiny's Child thing."
- 2006
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April 25
A New Disc Among Rumors
Eight months after the release of her debut album, Rihanna releases her sophomore album, A Girl Like Me. The album boasts Billboard Hot 100 chart-toppers "S.O.S." and "Unfaithful," and earns her four Billboard Music Awards, including Female Artist of the Year. But the success is paired with gossip that Rihanna is romantically involved with her mentor Jay-Z, who is dating pop star Beyoncé. "At first I was like, 'Ha ha, it's funny,'" Rihanna tells the AP. "Now I just ignore it and I'm numb to it...You cannot stop people from saying what they want to say."
- 2007
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March 29
An Edgier Look & Sound
Rihanna follows the likes of Janet Jackson and Christina Aguilera when she sheds her innocent image for an edgier look and sound. She releases the single, "Umbrella," which reaches the top spot on Billboard's Hot 100 in June and kicks off her upcoming third album, Good Girl Gone Bad. "It shows such growth for her as an artist," Jay-Z tells the AP." "If you listen to the lyrics to that song, you know the depth and how far she's come."
May 07
A Natural Beauty
After becoming the face of Cover Girl cosmetics, Rihanna appears in PEOPLE's Most Beautiful issue sans makeup. "The best thing about going without makeup is that it takes a lot less time to get ready," Rihanna tells PEOPLE. "You feel comfortable and free." The glowing singer is also listed at No. 8 on Maxim's Hot 100 and No. 59 on EW's 100 Stars We Love, among such up-and-comers as Hayden Panettiere and Shia LaBeouf.
June 05
Good Girl Gone Bad
Rihanna's latest disc, Good Girl Gone Bad, debuts at No. 2 on Billboard's Top 200 album chart. It features songs produced by Timbaland, cameos by Jay-Z and has a track, "Rehab," written for her by Justin Timberlake. "'Good Girl Gone Bad' was an expression of where I am at this point in my life, where I am in my career. It just represents my rebelliousness," she tells EW.
- 2008
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February 10
Rihanna's First Grammy!
After making a splash with an even shorter do, Rihanna performs "Umbrella" and "Don’t Stop the Music" at the 2008 Grammy Awards. The 19-year-old singer also goes home with her first Grammy for Best Rap/Sung Collaboration with Jay-Z for her hit "Umbrella." During her acceptance speech, Rihanna says, "Dad, I know I promised you I'd give you my first Grammy, but we're going to have to fight for this one!"
2008
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R&B Duo: Rihanna & Chris Brown?
After adamantly denying being involved with actor Josh Hartnett, Rihanna is romantically linked to 18-year-old R&B star Chris Brown (pictured at Clive Davis' Pre-Grammy Party). "He's one of my closest friends in the industry," Rihanna tells Allure in January. "He makes me feel like a teenager. I have to act and think like an adult so much. He makes me feel young again." In February, the pair is spotted awfully close in a pool in Jamaica.
March
Rihanna Covers Cosmo
Now a household name, Rihanna appears on the cover of Cosmopolitan, with newfound self-confidence. "A year ago, I would have sat here in my shell with my hands in my lap and been very shy," she explains to the magazine. "But now, I can be goofy and outgoing." The Grammy winner also gets to celebrate another single, "Don't Stop The Music," heating up the Billboard charts, reaching No. 3 – right behind Chris Brown's "With You."
June
Rihanna's "Very Close" With Chris
Continuing her magazine cover domination, Rihanna appears on the cover of Elle, where she briefly unseals her glossy lips regarding her "friendship" with Brown. "We've always been friends," the singer, who is currently on tour with Kanye West, tells the magazine, "but we're very close now."
- 2009
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February 08
Domestic Violence Drama
Rihanna and Brown are embroiled in a domestic violence drama that results in Brown, 19, being charged with two felonies in the alleged beating of Rihanna. "Words cannot begin to express how sorry and saddened I am over what transpired," Brown says in a statement. In June, Brown is sentenced to five years probation and 180 days of community labor.
November
Rihanna's Release
Having not uttered a word about her assault, Rihanna steps forward in fashion, before breaking her silence about the incident. "This happened to me...It can happen to anyone," the singer, 21, tells ABC's Diane Sawyer. Rihanna – whose latest album, Rated R, sells 181,000 in its first week – adds of Brown, "He was definitely my first big love."
- 2010
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January 31
Grammy Repeat
Rihanna wins her second Grammy award for "Run This Town," a collaboration with Kanye West and Jay-Z. "I just want to thank Kanye and Jay-Z for giving me the opportunity to be apart of such a wonderful song," she says in her acceptance speech. In 2008, she won her first Grammy in the same category with Jay-Z for the hit, "Umbrella."
Rihanna Plays the Field
After her traumatic relationship with Brown, Rihanna finds love again with Los Angeles Dodgers outfielder Matt Kemp. "I have such a chaotic life, but at the end of the day, that is just my peace," she says of her "easy" relationship with Kemp. "It keeps me sane, really, talking to him and talking to my family." By the end of the year, the couple calls it quits.
November 16
Getting Loud
Almost a year after the release of her last effort, Rihanna tops the charts with Loud, which boasts hit singles, "What's My Name?" and the Grammy-winning dance recording "Only Girl (In the World)". "What Loud showcases best…is a star undefeated by her worst circumstances – and finding redemption in exactly the kind of pop nirvana that made her famous in the first place," raves EW of her fifth album.
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