Age: 27; February 20, 1988

Rihanna is a multi-Grammy Award winner with a singular voice, stunning Barbadian good looks and questionable taste in men. The Umbrella singer's on on-again-off-again relationship with the physically abusive R&B singer Chris Brown has many fans and friends wringing their hands over the Good Girl Gone Bad.

The ugly side of RiRi and Brown's romance became widely publicized in 2009 when the "Hate That I Love You" singer's then-boyfriend brutalized her in his car before the Grammy Awards.

The daughter of a cocaine-addicted father, Robyn Rihanna Fenty
picked herself up and continues to make incredible music: "Only Girl (In the World)," "What's My Name?" and "S&M," to name but a few.

With a natural pathos to her voice and a beauty that shines through her music, the Music of the Sun singer's success was all but destined. Discovered by record producer Evan Rodgers, while Rodgers was vacationing with his wife in Barbados, RiRi immediately blew away everyone who heard her, including Jay-Z, then CEO of Def Jam Records who signed her on the spot when she was just 16 years old.

Critics initially complained Rihanna's style and sound were too similar to Jay-Z's wife Beyoncé. But after her second album, the A Girl Like Me star chopped off her hair, dropped her teen pop image and proved she was her own woman.

One of the highest selling digital artists in history, RiRi has won critical acclaim and collected a dazzling number of awards and distinctions, including being the youngest solo artist ever to achieve 12 No. 1 singles on the Billboard Hot 100 chart.

The Unapologetic celeb has made the Maxim Hot 100 every year from 2007 to 2012, and with parts in Battleship and End of the World, the sexy singer has proven she can act, too.

Despite her success, Rihanna continues to make some questionable decisions–reconnecting with Brown (collaborating on two songs in 2012, "Birthday Cake" and "Turn Up the Music," and then rekindling their relationship) and reportedly begging a tattoo artist to ink her face. Lucky for lovers of beauty everywhere, the artist refused.

No matter what mad turn the Barbados Babe takes next, Rihanna knows she can always find shelter with ardent fans who will make room for her under their umbrella… ella… ella.

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