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2. Lindsay Lohan

Lindsay Lohan’s penchant for bad boys (and occasional girls), booze, drugs and shoplifting lands her squarely on this list. The once-sweet and pretty teen star of destroyed her wholesome good-girl image for all time. Will she ever get it together? Jail, rehab and a reality show didn’t seem to do the trick. She’s recently hinted about running for president in 2020, but we just can’t take her seriously. It’s going to take a miracle to turn her reputation around.

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Lindsay Lohan Winking
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