9. Kelly Rutherford (Lily van der Woodsen)
Kelly played Serena’s mother on the hit series. Since Gossip Girl ended, Rutherford starred in a number of made-for-TV movies on Lifetime. Then her career was put on hold as she spent nearly three years in court divorcing her ex-husband, Daniel Giersch, and seeking custody of their children. Kelly spent over $1.5 million in legal fees and had to file for bankruptcy in 2013.
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