Dr. Dre and Nicole Young – $2 Million

Hip Hop icon Dr. Dre and his band of brothers from the NWA had a reputation for telling hard-hitting stories through music. They were also pretty popular with the ladies, which is why Dre himself has fathered four children from four different women.

But when he met Nicole Young, that changed, marrying her in 1996. While his previous partners had reported that he was abusive towards them, Nicole reported any of this. She did eventually file for divorce, though, in 2020, due to irreconcilable differences. He still covered her immediate finances with a $2 million payment. He is currently recovering from a brain aneurism he suffered in 2021.