Anna in the Tropics at American Players Theater: Longing for the Perfect Relationship
Above: Sam Luis Massaro as Cheché (r) speaking with one of the cigar rollers about quality in a scene from Anna in the Tropics. Below: Sam Luis Massaro
by Jonathan Gramling
If ever a play had been written for an actor — not a part, but the play’s essence — Anna in the Tropics, now being performed at American Players Theater, was written for Sam Luis Massaro. Anna in the Tropics parallels and intersects with Massaro’s own family history.
“My great-grandparents on my mom’s side — I come from a long line of Cuban Italians – everyone emigrated to the U.S. at the turn-of-the-century in the 1900s,” Massaro said. “My Italian side settled in New York and New Jersey first and then came down to Florida. And the Cuban side of my family came directly to Tampa where the play takes place. And that’s where I was born. I was born about five minutes from Ybor City. And my grandfather and I would go to Ybor every few days and get lunch across the street from the apartment where he was born sixty years prior. There’s a lot of old architecture, a lot of old history. And another crazy tie to this play is my great-grandparents met rolling cigars in a cigar factory. This play is full of my blood in a really cool way.”
Massaro didn’t come to the theater until high school. But the stage was in his blood.
“My intro was through my grandmother,” Massaro said. “We’re talking about my dad’s side of the family. My maternal grandmother was born and raised in New York and was a dancer. She danced on Broadway in the original company of shows like West Side Story. It was golden age in the 1940s-1950s on Broadway. She retired early to Florida where she had my father and my father had me. When I was 10-12-years-old, I took a liking to musical theater. I don’t remember how. I feel like I heard it somewhere. My grandmother got really excited because I was the grandchild who liked what she liked. And so she taught me musical theater scores. We would drive around in her car and she would play the original cast of Rogers and Hammerstein shows and Rogers and Hart shows and Lerner and Loewe shows. I still retain all of that information.”
When Massaro graduated from high school, he was accepted in the acting school at Florida State University. Massaro had also prepared for a medical career and at the end of college, he was accepted to medical school and to acting school at UC-Irvine. His father gave him some advice.
“My dad looked at me and said, ‘You’ve got to go to acting school because if you don’t, you’re going to regret it for the rest of your life,’” Massaro said. “I said, ‘You are absolutely right.’ And so I did it and haven’t looked back. My dad was a financial planner for a very long time. And I think he always dreamed of becoming a professional golf player and he just never did. He got married at a young age. I think he is proud of whom he raised and the people he created. But I think I he saw in me an opportunity for me to chase a dream that he wasn’t able to at a young age.”
It was at UC-Irvine that Massaro first met people from the American Players Theater. But it would be some time before Massaro’s and APT’s paths would cross again.
“I bopped around after Irvine as most actors do,” Massaro said. “I spent some time in New York and worked there. The pandemic happened and I took a few years off and tried my hand at not being an artist for a little bit. I worked professionally in the tech world. And then acting called me back and it was actually APT that pulled me back. I’ve been working here for the past three seasons. In 2023, they made me an offer and I said absolutely.”
Little did Massaro know that the play Anna in the Tropics was being considered. When he found out that it would be performed this year, Massaro felt he had to be a part of it. But he still had to go through the process.
“The director, Robert Ramirez who is fantastic, I worked with him on Much Ado last season,” Massaro said. “And we were in the room early on and he kind of asked me if I had heard of the play. And I said, ‘Have I heard of the play?’ I told him my connection and he got really excited. And he urged me to speak to Brenda and Carey and the artistic team and tell them my history with the play and I did. And then we started talking about the possibility of coming back this year and being a part of it. And I had to. It was a no-brainer for me.”
The setting for the play is a cigar factory in Ybor City — a part of Tampa, Florida — in the 1920s. The workers hand roll cigars made with Cuban leafs all day and to help pass the time, they hire a lector who reads books to them while they roll. The book that the lector is reading is Anna Karenina by Leo Tolstoy, a romantic novel about forbidden love. When Massaro learned he got a part, he immediately threw himself into research about the play, almost literally.
“I immediately started researching the rolling of cigars,” Massaro said. “There is a factory in Tampa that still does it by hand. I went to this factory and learned that this was happening and organized a tour for myself and my family while I was visiting home for the holidays. And we got to roll cigars. They taught us how to roll cigars, the traditional way of doing it. We got to tour the entire factory and look at all of the machines and equipment that people used. And at the top of this factory in this small room were 7-8 desks and they were rolling cigars by hand. We got to sit down at the table and roll them too. It can be monotonous, but there is so much history in it and technique. I rolled five, terrible cigars. They were atrocious. But I’m watching a gentleman who has been doing it for 35 years. This is his craft. And he’s doing it in a eighth of the time and it is perfect every time. It’s artistry. It can be monotonous, but it really is artistry.”
Massaro plays Cheché, a kind of supervisor who does quality control with the rolled cigars.
“Cheché is a nickname,” Massaro said. “His name is Chester. He is the brother-in-law to the owner of the factory. And he is an outsider. He shows up one day and one of the characters in the play has this awesome speech where she is playing. He shows up with a birth certificate and says, ‘I’ve been living in New England for the past 10 years, but we have the same father. So I want to live and work here now.’ And this Cuban family — as most Cuban families are — is incredibly generous. They open their doors and say, ‘Okay. This guy who we do not know, come and work with us. And you are a part of our family now.’ He moves through the play as an outsider.”
Cheché doesn’t really fit in with anyone.
“He didn’t grow up in Tampa and no one really knew him for the first 30 years of his life,” Massaro said. “He doesn’t move through the world with as much grace and artistry as other people in the play. It’s a super poetic play. The language in the play is stunning. And my guy gets one paragraph where he talks in metaphor and imagery. He’s not that guy. He’s a numbers guy. He’s an analyst. He likes detective stories, not romance novels. Everyone calls him a clown. He’s the black sheep of the family. And I think he feels that way for most of the play.”
In some ways in Anna in the Tropics, art imitates life which imitates art.
“At the center of it is this woman who wants something different, who isn’t fulfilled by what she has,” Massaro said. “And there is some incredible passages in that book — and the play talks about them too — where Anna Karenina doesn’t necessarily want to leave her husband. But she just isn’t satisfied with her husband, so she wants more. She’s hungry for something that she has been missing. And that is a lot of this play. All of these people are missing something. My character is missing his wife. My wife ran off with the last lector. My wife ran off with the last guy who was reading a book to us. And so I have a lot of opinions about this guy who is reading to us now. I hate this guy. And so we’re all missing something and how do we grapple with that loss. How do we shift and continue to move forward just like Anna Karenina does in the book.”
Anna in the Tropics is a story about survival and love all rolled up into one excellent play that keeps the audience engaged.
“To my recollection, this is the only time that this play has been produced outside,” Massaro said. “This is a unique experience. It’s a play that won a Pulitzer in 2003. It’s a play that is incredibly poetic and brilliant and poetry audiences here have never heard. It’s outside in the heat and the mugginess that exists in the world of Tampa in the 1920s. You’re not ever going to be able to see a play like this ever again. And I think it makes it all the more earth shattering. It’s seismic. Come see it. We are one week into rehearsal and I’m really proud of all of the work that I’ve done here. But I’ve never been this proud. And it’s only been one weekend. I really think it is going to be singular. And I really want people to come see it.”
Tampa can be steamy in the summertime. Anna in the Tropics turns the temperature up a few degrees as it explores what is important in life. Not everyone finds the answers.
