Alyssa Milano

Two primetime hits, eight seasons each, across back-to-back decades. That's Alyssa Milano's actual career record, and it tends to get buried under everything else. She was 10 when she got Who's the Boss?, having already beaten out 1,500 girls for the touring company of Annie at seven. When the teen-icon run ended in 1992, she didn't disappear. She joined Charmed as Phoebe Halliwell in 1998 and found another generation of fans. Not many actors get one sustained franchise. She got two.

Her 2017 tweet amplifying Tarana Burke's #MeToo hashtag generated 12 million Facebook posts in 24 hours and made her the public face of a movement she didn't actually found. That gap has followed her around ever since. The acting is now a footnote to the brand. She swapped her Tesla for a Volkswagen to protest Elon Musk in 2022, which would have been a cleaner move if critics hadn't immediately noted VW's origins under the Nazi regime. She left X entirely after Trump's 2024 win. Whether any of it moved the needle is a separate question.

The $10 million fraud lawsuit she filed against her former business managers in 2017 alleged they left her and her husband millions in debt with ruined credit, including a home renovation that cost $5 million on a house worth no more than $3 million. It settled out of court in 2019. Meanwhile, her time on Charmed has its own unfinished business. Co-star Holly Marie Combs alleged in 2023 that Milano threatened to sue for a hostile workplace and gave producers an ultimatum over Doherty, which Doherty backed up and Milano denied. The through line is that wherever she goes, things get messy.