#5: Alyssa Milano as Samantha Micelli
As Samantha, Alyssa Milano was the heart of the show’s coming-of-age stories. Audiences watched her character transform from a streetwise kid into a young woman finding her place in the world. Her close bond with Tony and her spirited independence gave the series much of its warmth and relatability.
When Who’s the Boss? aired, Milano became one of television’s brightest teen stars. She quickly crossed into pop culture as a role model for young viewers, balancing school, acting, and a growing fan base. Her popularity expanded internationally, especially in Japan where she launched a successful music career.