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Katy Perry's road to fame was bumpy. Before becoming a chart topper with infectious hits like " Firework," "Hot N Cold" and "The One That Got Away," the daughter of devout ministers tried to make it on the gospel circuit, released a failed Christian pop album at 16, was dropped from several labels despite working with respected production team The Matrix and was broke by 22. But what didn't kill her apparently made her stronger. With the 2008 release of One Of The Boys and the decidedly anti-spiritual single "I Kissed a Girl," she, her pin-up and looks and retro girlie aesthetic became a global phenomenon complete with Grammy nominations, wacky world tours, even wackier outfits (Remember the sparkler bra?) and too many awards show performances to count. Her sophomore album, Teenage Dream, was an even bigger success, containing collaborations with Kanye West ("E.T.") and Snoop Dogg ("California Gurls") and spawning enough No. 1 singles to tie Michael Jackson's record. Unfortunately, her love life has not been as golden. After exchanging promise rings in 2008, things fizzled with Gym Class Hero Travis McCoy. Comedian Russell Brand proposed while vacationing in India in 2009 after only four months of dating. The twosome held a days-long ceremony there less than a year later. But as documented in her concert film Katy Perry: Part Of Me, the union disintegrated quickly and he filed for divorce a mere 16 months later. She has since moved on with Florence + the Machine guitarist Robert Ackroyd and John Mayer, who she dated sporadically from 2012-13. At least she has cat Kitty Purry to keep her company!