Printable Book Club Questions for Leading Men by Christopher Castellani

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?