In this ShowbizU interview, Tim Kashani talks with his wife, Broadway actress Pamela Winslow Kashani, about her artistic origins, training, and career trajectory. Pamela recounts beginning in a church choir at age eight, being placed in an adult choir, and attending the French Woods Festival where she landed a role in Chicago. She describes eight years of intensive study, including Saturday acting workshops and a degree from Carnegie Mellon, culminating in her Broadway debut as Rapunzel in the original company of Into the Woods at age 21, working alongside Stephen Sondheim and Bernadette Peters. She reflects on the “10,000‑hour” rule, mentors such as Liz Orian and Mel Shapiro, and advises her younger self to have stayed longer in the show. Pamela discusses the evolution of her professional etiquette onstage and on set, the shift in perception when she moved into producing, and the importance of seeing actors as creators who can also produce. She explains her current work with the Theater Accelerator, mentoring emerging writers, storytellers, and actors, emphasizing gratitude for her own mentors and the value of giving back. The interview blends personal anecdotes, career advice, and insights into the collaborative nature of theatre production.
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What do you get when you have a Broadway professional and a camera crew? Long story short, you get a lot of cool info when you get Showbiz U Luminaries. Welcome to another session from Apples and Oranges Arts Videos. Today I'm going to be talking to Pamela Winslow Kashani, also known as my wife. Pamela, where did your artistic career begin?
My artistic career began in church choir. When I was 8 years old, my choir director noticed that there was something different about me, is that my voice was so incredibly loud that they decided that they would put me in the adult choir. And I thought, oh, this is fun because then I get to read music 3 times a week and I get to be in music all the time, all week long. And I developed my, honed my singing skills and my musical skills through that and through taking piano as well. And put it on the back burner and just went along with my life. And then I was invited to go to a performing arts summer camp, which some of you may know, French Woods Festival of the Performing Arts. A lot of really amazing people have come out of that program. And I had no idea. I went in completely blind. And I brought whatever music I had because I was I was told that I had to audition while I was there, which was bizarre. And so I ended up showing up to the big audition of the summer, and I put on my perfect Laura Ashley dress, and I sang Mendelssohn's "O Rest in the Lord," a beautiful aria, and I got cast as Cell Block Murderess Number 2 in the musical Chicago. And from that moment on, I knew that I wanted to be a performer and nothing was going to stop me.
Then as a performer, you're 13 at the time?
Mm-hmm.
What was the trajectory?
Bad perm, chubby, like just didn't know who I was, no idea, but I had this, this drive and somehow I was going to figure it out.
And there's a lot of 13-year-olds right now that go to a Broadway show and they say, "That is me. I want to be on that stage." Yes. How did you get from being 13 with a bad perm to getting a wig person who then dressed you every night to go on stage in your debut as Rapunzel in Into the Woods at age—
21.
8 years. What happened in those 8 years?
In those 8 years, I got serious and I studied. And I had wonderful parents who were incredibly supportive of me. I studied really hard and I found some wonderful teachers. And through French Woods, I found wonderful acting teachers. And joined an acting workshop on Saturdays. And I was lucky enough to live close to New York that I could come and see shows and I could study. And thankfully, it got me into a wonderful program at Carnegie Mellon, and that's when I got really serious about my acting skills and merging that with my performing skills.
It's not common that everybody graduates from college and gets right into a Broadway show.
That's true.
What was that like?
It was my, my own personal fairy tale. It was— I was shocked. I couldn't believe it. Two weeks after I graduated from college, I got sent a principal contract to be on Broadway in the original company of Into the Woods and play opposite Bernadette Peters. It was a small role, but it was definitely a role that I could sink my comic chops into and my, my voice and all the things that I had at that time to bring to a role. So it was an absolute dream, and I got to work with Stephen Sondheim and Paul Gemignani and just all these masters of the form. And it's really always been one of my most cherished times, was it was the time that I got to do Into the Woods and learn from those incredible artists.
What did you have in your bag of tools that prepared you for that moment, and what do you, in hindsight, wish you would have known back then? Start with what you had in your bag of tools.
What I had in my bag of tricks was I had enough stage time. I had done the 10,000 hours— what is that theory? You probably know it better than me— but you put 10,000 hours into something, and then ultimately you you find that you're able to make an impact in the world with it. And I had done all of that due diligence, and I felt really ready for this opportunity. So when it came up, I was nervous when I was in the auditions and the callbacks, but I also had this inner sense of confidence that I, I could bring to the table whatever. I was confident about what I had. I didn't know it was going to be what they wanted, but I felt pretty good about what I had. I had excellent mentors Liz Orian was my acting guru for 4 years at Carnegie Mellon. Mel Shapiro was a visionary director, producer, acting coach, and I, I had great training, and it helped me. It helped me develop what I had and also be confident with it.
And now, if you could go back in that time machine and talk to yourself at that point, what advice would you give yourself? That you didn't have in your bag of tools?
I probably would have stayed in the show till the end of the run because I felt— I left the show after 14 months, after my year contract. I was in the previews and then my contract kicked in and I did the show for 14 months and then I felt like the show wasn't teaching me anything anymore. It was a wonderful job but it wasn't pushing my career forward anymore. So I left the show, and all the other actors thought I was nuts, and they were right. I think I should have stayed in the show.
It worked out okay for you.
It actually worked out really well because I left the show, and then I was on vacation, and 2 weeks later they called and they said, Kim Crosby has got a movie, and will you come back and play Cinderella for 2 months? So I never would have had that opportunity.
So don't go back and talk to yourself. It worked out, worked out quite well.
And then, no, it worked out fine. I guess I shouldn't then.
Yeah. If you look at then, you've done TV, you've done film, there's still craft involved in that, but what are some of the subtleties, some of the nuances that take time to build relationships with people and also onstage etiquette or on-set etiquette?
Yes, yes, I think I was a lot more brash and brazen back then and I was all about my show and my performance and not as good of a team player as I am now, I would say. And I think I also appreciate a really strong work ethic and a positive attitude, whereas before I was able to tolerate people that are not nice, people that are just rude for the sake of getting it done. And I'm not like that. And I realize that, and you know, in our company, we always surround ourselves with people that are positive because I learn better, I do better, I think other people do better with a positive environment. So I'm always trying to create that.
And now putting on your producer hat, now you're seeing a whole different side of the table when you're looking at this business from a, from a producer. When you were acting, I'm sure you viewed producers as a certain, a certain way. What's the biggest difference that you've learned now that you're on the other side?
Producers are just people, and most producers are people that really like theater, and many producers are actors or former actors. We're all connected. There's not this great divide, and it's very true, when I was younger, producers had this this otherworldly separation between an actor and them. And it's, it's really just a perception because actors produce too. And the best actors know how to create. They write, which now I'm doing a lot more of in later in my life. They direct themselves because sometimes the direction that you get may not be the direction that you need to get you somewhere. And I remember this is something Liz Orien told me. She gave me some flak for a scene I was doing, and I said, "You're giving me direction notes." I said, "The director would give me these notes." And she says, "No, you need to know where you want to go with this character, and the director will help you get there." But you need to put a director hat on too, if you don't have a good director. So the, the, what I'm trying to say is actors are producers too, and that third eye that you develop, that sort of macro vision of your role and how it plays in the whole piece, is what producers do. They're looking at the big picture. They're looking at where this piece sits in today's audiences and where it's going to— is it going to be a Broadway show? Is it going to be an Off-Broadway show? Where does it fit in? All of that is something that an actor needs to develop when they're looking at a character within a play which has a message. And understanding that whole big picture is part of what all creative people do. I feel more vulnerable now than I did way back then. And I don't know why. There's a lot more stability in my life now. But I always feel dipping my toe into a new character or a new project, I get this tingly feeling. I still have it inside. And I never want to lose that because that's the magic. That's where you connect viscerally as an actor to what you're doing. That's what other people are going to see and relate to, too, and make that skin jump. That's something we talk about in the Theater Accelerator. Only when the actor so sincerely is feeling that, that openness and that rawness, that's the only time the magic can happen. But at the same time, you don't want to be a puddle of emotion and fall apart every time an audition doesn't go that great or you didn't— the outcome didn't work the way you tried or it's a horrible hair day and you had a final callback. You have to have a tough skin and a soft inside, and that I think is a life's work.
And now you're mentoring another generation of writers, storytellers, actors. How has that helped your own acting career?
So much, so much. So now I'm the old lady, and I actually like it. I enjoy it. I find it tickles me to death when people admire me, and it's, it's an honor to be looked at for advice and I'm more than happy to do it because I know that in my life, my mentors, without them, there's no way I would have been able to have the life that I've had. And I'm grateful and I want to give back.
