8. Roseanne Barr and Tom Arnold
Back in 1990, Barr very famously got upset with her lawyer for simply suggesting she have Arnold sign a prenuptial agreement. She ultimately chose love and trust over signing a piece of paper and fired her lawyer shortly afterward. However, four years after they became husband and wife, Arnold and Barr’s martial bliss came to a screeching halt. Their divorce became one of Hollywood’s ugliest at the time, plenty of unpleasant accusations flew between the two and there was even a restraining order issued. When the dust finally settled, Barr lost $50 million which Arnold used to get himself back on the right track. He didn’t walk away from the marriage completely untouched though. Barr may have regretted not signing a prenup but Arnold must have regretted getting a large tattoo of Barr’s face on his chest.
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