TV star Alyssa Milano is rocking Chicago as Broadway’s newest Roxie Hart. The Who’s the Boss? and Charmed alum is fulfilling a lifelong dream by stepping onto the stage in the long-running revival. Entertainment journalist for Spectrum News NY1 Frank DiLella recently caught up with Milano following her opening night to chat about the thrill of going back to her musical theater roots, dancing Bob Fosse’s iconic choreography, and much more.

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You made your Broadway debut on Monday night in Chicago. A Broadway debut is a big moment, and it only happens once. Take me back to that night.

It was special. It wasn’t special only because of the work — it was also special because it’s this show with these people. This show is such an institution. There’s an incredible history of talent who’ve played the role of Roxie. But beyond that, this cast is lightening in a bottle!

Was Chicago always on your radar?

I saw the show many eons ago. I knew about the show, but it was never on my radar to do it. I never really thought I would make it to Broadway.

Really? You started out in musical theater.

Yes. I started out on the national touring company of Annie, and so I think Broadway was the goal, but I don’t know if I ever thought that I would make it because “life,” as Roxie would say. Life is what happens when you’re busy making other plans. And I just thought my career had taken such a different direction, with television and film. And people in the industry love to sort of consider you in one category. So I don’t know if I ever thought that I would make it to Broadway.

You did a great job of documenting your Chicago journey on Instagram, from costume fittings to rehearsals to opening night.

The thought was — someone had asked me before I started — you should bring a diary and take lots of pictures. And I thought I can use Instagram as the diary and leave the time stamp for this part of my life. And also give people the insider’s perspective of what goes into creating a character and stepping into a show like Chicago that’s up and running and an institution.

What was your favorite part of this process?

Performing the show. Throughout the rehearsal process, it feels so foreign because you’re not working with the orchestra, you’re working with a piano. You’re not working with other actors, you’re working with the dance captain and stage manager. So it doesn’t feel real.

What do you remember from being out on the road with Annie as a kid?

I don’t remember a lot from that time because I was 8.  But I remember loving singing and dancing and performing and hearing the applause. It felt like I was doing the thing that I loved.

When were you first introduced to theater?

Annie. I saw it on Broadway for my 7^th birthday and thought I want to do that! And then I went out for an open-call Annie audition — 1,500 kids were there and four were picked, and I was one of the four for the second national touring company. I was really a theater kid, and then I got Who’s the Boss? out of New York when I was 10.

Going back to Chicago, what was it like diving into that great Bob Fosse choreography?

Fosse is the most miraculous choreography to perform because every moment is a dichotomy:  It’s the pull and the push and the give and the take and the tease and the control. To me, as an actor, trying to figure out how those moments support the story and Roxie’s journey. I’m playing Roxie a little different; to me, her journey is because she didn’t make it in vaudeville. And her newfound fame is giving her a taste of that thing she always wanted. And it’s become a drug to her. And although I’m staying true to the Fosse choreography, I’m not as polished in my portrayal of the dancing. And that leads so nicely to the “Nowadays”/“Hot Honey Rag” at the end where she has to form this alliance with Velma and has to create this vaudeville act. 

Some amazing women have played Roxie over the years. Is there a Roxie who you look up to the most?

I look up everyone — I’ve done the deep dive. Ann Reinking inspired me the most and inspired my Roxie a lot. The volatility. There are very few videos of Annie doing Roxie. The video that’s there, there’s a volatility that made it like the emotional Olympics, where she could turn on a dime. And there was a strength to her that I’ve tried to instill in my Roxie. There’s a broad factor to her Roxie.

You’re now a part of the Broadway community. What’s your favorite thing about this very special club?

That it is a community. There’s a part of doing TV and film where it’s very easy for people to go in and close their dressing-room doors in between takes and be as isolated as you choose to be. You can eat alone, run lines by yourself in your trailer. But being a part of something like this, where everyone’s dressing room doors are open, where you’re stretching together and sweating together, you’re lifting each other up in moments. It feels how it’s supposed to feel because it’s a vulnerable position to be in, acting and performing. And so we all need that community.

Chicago may be set decades ago, but it’s so timely, especially with how as a society we’re obsessed with fame and celebrity.

I think that’s why Chicgao still works and is still on Broadway: It’s timely and timeless. The main theme that’s most relevant is how our media creates a celebrity and how that machine does not stop, and sometimes people don’t warrant being celebrities. When you look at Roxie’s storyline, every time she’s down, she creates another part of her story and then she ends up back on top.

What’s your next Broadway dream job? Are you here to stay?

I’m just trying to be really present and in-the-moment. Reflecting back on my four-decade-long career. I think the reason why I’m still working is because I take advantage of the opportunities that are given to me. And I feel like they’re presented to me when I need them. Meaning, I feel like this opportunity found me when I needed to be reminded of the pure joy of creating a character and being that character for two and a half hours.