America loves a good success story. That’s why celebrities are in fact celebrities. We love to see how the other half lives and we love to see people succeed. America also loves to see those celebrities fail and fail hard. There’s something really interesting about hearing about a female celebrity who has run into legal trouble. Some of the female celebrities on this list are habitual offenders and others are ladies you probably forget ever got themselves into trouble.

Paris Hilton

Paris Hilton kicks off this list and there is literally no one who is surprised by this appearance. It’s actually a bit of a surprise that she’s only ever served three days in jail for violating parole and driving without a license.

Lindsey Lohan

Lindsey Lohan has had a number of stints in jail for various offenses that include drug possession. Lohan has spent as many as 14 days and as little as 84 minutes.

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