Tony Danza Reveals Why Alyssa Milano Was the Perfect Choice for Who’s the Boss?

Tony Danza is looking back on a defining moment from his career — the day he knew Alyssa Milano was meant to play his daughter on Who’s the Boss?

In a new interview, Danza, now 74, recalled how Milano landed the role of Samantha Micelli when she was just 10 years old. At the time, producers were seeing many child actors who felt overly polished. Danza knew that wasn’t right for the part.

Then one audition stood out.

Milano arrived with a black eye — something that later became a key detail in the show’s pilot episode — and instantly won everyone over. Danza says she felt real, natural, and completely right for the tomboy role of Samantha.

Danza starred as Tony Micelli, a former baseball player and single father who becomes a live-in housekeeper. The sitcom, which aired from 1984 to 1992, also starred Judith Light as Angela, Tony’s successful and driven boss, Katherine Helmond as Angela’s outspoken mother Mona, and Danny Pintauro as Angela’s young son Jonathan.

From the start, Who’s the Boss? broke TV norms. It flipped traditional gender roles by placing a man in charge of the home while a woman built a high-powered career. Danza says that choice was intentional and central to the show’s identity.

The series also avoided turning Tony’s job into a joke. Instead, it treated his role with respect while still finding humor in unexpected moments. Danza remembers scenes that highlighted the show’s confidence and wit, including one where Angela casually introduces Tony as her housekeeper — to hilarious effect.

Even decades later, Danza says the show holds up. He recently watched an episode from season 5 — without sound due to a technical issue — and was impressed by how clearly the story and performances came through.

What makes him most proud, though, is the show’s heart.

Danza says he was always mindful that families were watching together. He wanted parents to feel comfortable and kids to walk away with positive messages. While Mona’s cheeky jokes sometimes pushed boundaries, he believes the show struck the right balance.

That reflection was sparked while promoting his new film, Re-Election, where Danza plays the father of a man obsessed with reliving his high school glory days. The movie’s themes of regret and unfinished business hit close to home.

Danza admits there was a moment after Who’s the Boss? ended when he may have taken a wrong turn professionally. Focused on staying in sitcoms, he turned down a dramatic role that, in hindsight, might have opened new doors.

Still, he doesn’t dwell on it.

As Danza puts it, being stuck fighting the past only holds you back. Looking forward — with gratitude instead of regret — is what truly matters.