9. Britney Spears
Britney Spears was making photographers hundreds of thousands of dollars thanks to her reckless behavior back in the day. Britney would head on out to the nearest club, and it almost seemed as if she would make sure she wore no panties because every time she stepped out of a car, her private part was on full display. Photographers have probably caught Britney without underwear more than three times in one year. You would think Britney would learn from the first time it happens. Oops! She did it again.
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