Book Club Questions for Leading Men by Christopher Castellani

This post contains links to products that I may receive compensation from at no additional cost to you. View my Affiliate Disclosure page here.

Leading Men by Christopher Castellani is about the turbulent fifteen-year romance between the famous playwright Tennessee Williams and Frank Merlo. The following book club questions will have spoilers so if you haven’t read the novel yet, check out my spoiler-free review first.

It’s July 1953 in Portofino, Italy. A young Truman Capote throws a party for the literary elite, drawing Tennessee Williams and Frank Merlo. This is where they meet the fictional Anja Blomgren, a young Swedish actress they decide to take under their wing, which sets a motion of events that will alter all three of their lives. Leading Men is a quiet look at the man behind Williams and what it means to stand in someone’s shadow and to sacrifice your own wants. It’s also about the consequences of words left unsaid.

Let’s get into the discussion questions

What was your initial impression of Tennessee and Frank’s relationship? How did it change as the story went on? Let’s discuss why the two were drawn to each other. Why wasn’t their love long-lasting?
While Frank loves Tennessee, he does struggle with living in his shadow. For instance, when people ask what he does, he decided to answer with, “I sleep with Tennessee Williams,” as a way to inspire a rise. But then he considers, “other than sleep with Mr. Williams, what had Frank Merlo done with his life?” Do you believe there was truth in that statement? Why or why not? How did that line foreshadow Frank’s motivation for something more?
Why do you think Frank was so insistent they take Anja under their wing? What was your thoughts on Anja at the beginning? We spend quite a bit of time with her as an older woman, why do you think the author placed such a focus on her? What did she represent compared to Frank and Tennessee? And what did they represent to her?
Chapter six shows the final interaction between Anja and Tennessee. Why do you think she decided to meet with him? Why did he give Anja his play?
The last play of Tennessee Williams is an imagined take on his regret with Frank. For not saying goodbye and in general, missing his great love. Was the play somewhat of an apology to Frank? What did you think about it?
Why do you think Frank decided to go help Jack and Sandro? Was it simply his inner desire to help people? Let’s discuss why everyone says Sandro killed Jack.
We go from Italy to Frank on his deathbed. Why wasn’t Tennessee there for him?
After Frank died, Tennessee never wrote another hit. Why do you think he wrote all his masterpieces with Frank? What about Frank inspired his work?
What do you think the title represents in the context of this book?
What’s your favorite Tennessee Williams play?

More fiction based on real people

Historical fiction centered around real people always makes for an interesting and insightful reads. Here are some more recommendations.

Love and Ruin by Paula McLain is about Martha Gellhorn, a fiercely independent, ambitious woman ahead of her time, who would become one of the greatest war correspondents of the twentieth century. In 1937, twenty-eight-year-old Martha Gellhorn finds herself unexpectedly—and unwillingly—falling in love with Ernest Hemingway, a man on his way to becoming a legend. On the eve of World War II, and set against the turbulent backdrops of Madrid and Cuba, Martha and Ernest’s relationship and careers ignite. But when Ernest publishes the biggest literary success of his career, For Whom the Bell Tolls, they are no longer equals, and Martha must forge a path as her own woman and writer.

You can order the book on Amazon here. Find the discussion questions here.

The Age of Light by Whitney Scharer follows Lee when she’s arrived in Paris from New York—she’s tired of being photographed and is ready to become a photographer. A chance encounter leads her to the famous Surrealist Man Ray where she convinces him to take her on as his assistant and teach her everything he knows. The two work closely together and eventually their personal and professional lives become intimately entwined, changing the course of Lee’s life forever. Lee’s journey takes us from the cabarets of bohemian Paris to the battlefields of war-torn Europe during WWII, from discovering radical new photography techniques to documenting the liberation of the concentration camps as one of the first female war correspondents.