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Why Drew Barrymore's Playboy Past Comes Back to Haunt Her On a new episode of "The Drew Barrymore Show," Drew Barrymore reflects on regretting her Playboy shoot at 19, urging parents to monitor kids' tech use in a heartfelt Drew Barrymore 'never knew there would be an internet' when she posed for Playboy, and said she wishes there Drew Barrymore was just 19 when she posed for Playboy in 1995. That’s more than anyone else, including Drew Barrymore is looking back on her Playboy cover with a new perspective, nearly 30 years later. We will revisit Of course, posing for the photographs on these pages isn't all that Drew has been up to lately. 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