Mary-Louise Parker – 56

Mary-Louise Parker first gained prominence in the late-90s for her craft, and then for her relationship with actor Billy Crudup. Their chemistry was electrifying, and they were soon to become parents, but sadly, this lovely duo split up even before the birth of their child.

To date, the reason for Mary and Billy’s separation remains a mystery, just as her second mysterious breakup with Jeffrey Dean Morgan. Both met while shooting for Weeds, started dating, got engaged, and then, suddenly came the unfortunate news. Still single, Mary enjoys her life with her children – a son William Atticus Parker and an adopted daughter Caroline Aberash Parker.