(Source: Pacific Coast News, Inset: Harper's Bazaar)
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20. Britney Spears

Harper's Bazaar, August 2006

When it came time to tell someone about her second pregnancy, Britney Spears chose none other than David Letterman. "Don't worry, Dave. It's not yours," Spears quipped when she visited The Late Show with David Letterman in May 2006. She appeared on the cover of Harper's Bazaar wearing nothing but a necklace before giving birth to son Jayden James Federline that September.