This reading group guide for Anne of Hollywood includes an introduction, discussion questions, ideas for enhancing your book club, and a Q&A with author Carol Wolper. The suggested questions are intended to help your reading group find new and interesting angles and topics for your discussion. We hope that these ideas will enrich your conversation and increase your enjoyment of the book.


Introduction

Not just any woman can be the Queen. Luckily, Anne Boleyn isn’t like the rest of the cookie-cutter Hollywood girls; sure she may be ambitious, but she’s a brunette in a town of bottle blondes, and she knows how to make the most of it. She’s witty, smart, fun, and sexy (but never slutty), a combination that attracts the eye and attention of Henry Tudor, reigning “king” of the Hollywood scene. But Anne soon finds that capturing Henry’s heart is the easy part. Surrounded by the schemers and social climbers of Henry’s Los Angeles “court,” struggling to figure out who she can trust and who is trying to topple her, the real question is, how long can she keep it? And what happens if she can’t?

What a king gives, the king can take away…as true today as it ever was.

Topics & Questions for Discussion

1.  From Anne’s perspective, what is it like to live in Hollywood? What is gratifying about living there, and what is frustrating?

2.  The characters may not be living in Tudor times, but gender and identity are as closely linked in the L.A. “court” of the novel. How would the story have been different if Anne and Henry’s roles had been reversed; if Anne were the queen, and Henry her consort? Do you think Henry, if he had been in Anne’s shoes, would’ve acted differently in the end? Discuss the role of gender and identity throughout the novel.

3.  Anne of Hollywood has a large cast of female characters who, directly or indirectly, have a heavy influence on Anne’s life. Discuss Anne’s relationship with each of these women; consider Mary, Theresa, Larissa, Anne’s mother, Lacy, Jane Seymour, and even Angela. What, if anything, does she learn from each of these women at various points throughout the novel? Do you think at times she learns the wrong lesson? Why or why not?

4. Throughout Anne of Hollywood, each character is motivated by personal ambitions, often to the point of betrayal. Do you feel these women (and men) would have been stronger had they attempted to form real friendships instead of turning on, or using each other?

5.  Power, and the balance of power, plays an important role in every relationship throughout the novel. Larissa’s power, for example, lies in her beauty, vivaciousness, and her abilities in the bedroom. What do you think Anne’s power is? Mary’s? Theresa’s? Discuss how each character, at one point or another, manipulates or abuses their power to achieve a particular end. In your opinion, do any of them succeed?

6.  Mary, though rather on the periphery of the story, is a very interesting character. How would you feel if your sister dated, and then married, a man you once had a relationship with? Conversely, how would you feel knowing your sister had slept with the man you married? What did you think of the relationship between the two sisters as compared to the relationship between Anne and George?

7. How do you view the various examples of marriage, romance, and sexual relationships in this novel? Discuss various examples. In your opinion, do any characters seem to find true love, or do most see love (and sex) as just another way to manipulate others in their Hollywood world?

8.  There is only one chapter written from Henry’s point of view (p. 54), and it is right after he and Anne have essentially ended their relationship. In this chapter, he reflects on a something his father once told him: “As you go through life, you’re going to find yourself in relationships that are no longer right for you, but you might still feel an attachment to the woman….I’m going to give you my best piece of advice, and it will always be the correct thing to do in these situations…leave before you’re ready.” (p. 348) Discuss this advice—do you agree or disagree? Were you surprised at all by Henry in this chapter?

9.  The Boleyn family has a motto: “To always do what will make you happy, not what will make you happy this minute.” (p. 222) Discuss this motto. Do you think it is a wise way to live? Do you think any of the Boleyn siblings actually follow this mantra?

10.  The novel is full of examples of blighted ambition and characters who feel trapped by circumstance. Even characters like Cliff, who realizes the emptiness of his existence, can’t seem to break free of the life to which they’ve grown accustomed. Do you think personal unhappiness excuses the scheming behavior or betrayals of some of the more antagonistic characters? Or did you find them entirely unsympathetic?

11.  What do you think Leo De Vince was trying to tell Anne in his studio, when he advises her to “Let go”? (p. 222) Do you think if Anne had taken this advice, things might have ended differently for her?

12.  If necessary, familiarize yourself with real story of Anne Boleyn. Then compare the characters in Anne of Hollywood to their real life counterparts. Does anyone’s story surprise you? Discuss any adaptations or changes the author has made.

13.  Despite her larger-than-life adventures, can you relate to Anne in anyway? What aspects of her character do you find universal? Have each member list the adjective they think best captures her character? Were you surprised by how others in your group perceived her? What are her strengths and her weaknesses? Was there any point where you found yourself thinking you would’ve reacted differently in her shoes? If so, discuss!

14.  Anne reflects, once her marriage has ended that “Anne Tudor was killed but Anne Boleyn is still hanging around.” (p. 353) Does your perception of Anne altered throughout the story, as she goes from Boleyn to Tudor to Boleyn? Do you feel Anne Boleyn at the beginning is very different from Anne Boleyn at the end? Do you see Anne Tudor as a victim of the web around her? Or do you think Anne herself played a part in her own “downfall”?


Enhance Your Book Club

1.  At the beginning of the book, Maren sends Anne tarot cards—and a message: the Queen of Cups stapled to the King of Cups, and a Queen of Pentacles (torn in half). Look into the history of tarot cards, and the meanings behind each card. For fun, consider bringing a tarot card reader to your book club meeting and have your fortunes told!

2.  Have a group history lesson. Have each member pick a character and do some research on their real life counterpart. Present your findings to the group.

3.  Read another novel featuring Anne Boleyn, one set during the actual Tudor time period (for example, The Other Boleyn Girl or To Die For) and discuss it at your next meeting. Which do you prefer, a modern retelling or a classic historical setting?

4.  Have each member create their dream cast for the Anne of Hollywood movie. Then, turn book club into movie night and watch a television or film adaptation of Henry and Anne’s real story, such as HBO’s The Tudors. Any casting overlaps?

5.  Leo de Vince’s cure for Anne’s woes is a slice of guava. Have each member bring their “comfort” food to the meeting, and enjoy a feast while discussing the book. Don’t forget to include guava!


A Conversation with Carol Wolper

The Boleyn family has a motto, and even Henry lives by the words his father told him, at least as far as his relationships go. Do you have a personal motto or maxim you live by?

There’s a line Anne says to Henry early on in their relationship that has served me well. She says, ”You can reject me but you can never, ever replace me.” That’s not exactly a motto but it’s a guiding principle. It’s a realization that competing with others is a waste of time. The trick is (personally and professionally) discovering what is singular and unique about oneself and maximizing and celebrating those gifts and talents.

Many books and films have been centered on the rise and fall of Anne Boleyn. What in particular drew you to this story and to these characters? What made you decide to set your tale in the modern day?

My girlfriends and I were obsessed with Showtime’s, The Tudors, especially the first two years that centered on Henry’s courtship and marriage to Anne. I started reading everything on Anne I could find and eventually realized that she is the ultimate cautionary tale about the upside and the peril that comes with dating a powerful man. I then realized that I’d been hearing variations of this story for the last fifteen years from friends of mine who have dated rock stars, CEOs, Wall Street guys, movie stars, super-star athletes etc.  What surprised me was that not all that much has changed since the sixteenth century. Alpha Males (and every community has their share of them) continue to be both alluring and challenging. They continue to be an ego booster as well as a great danger to a girl’s self-esteem. They continue to be potential saviors and potential destroyers. Once I saw that the template of sixteenth century sexual politics matched up so neatly with twenty-first century culture, I just had to write a book about it.

In the reality of the Tudor times, Henry was much more ruthless, and Anne was sentenced to death. In your story, Anne escapes with a new beginning, and even Henry is slightly more sympathetic. What made you decide to end your novel with a more uplifting tone?

Southern California has always been a place people come to for a new beginning and Hollywood has always been about fantasy and reinvention. Second acts are expected here, though far from guaranteed. It’s not an easy thing to pull off but if you’re smart, tough, and adaptable, it can be done. There’s no question Anne was smart (not just well-educated but also clever), tough (she navigated though some very rough court politics to get that crown on her head), and would (I believe) have been adaptable had she lived in a time when options were available. A twenty-first century Anne would take her punches and live to fight another day. She would tap into her inner Tina Turner and walk away from Henry with nothing but her pride and her determination to not only survive but eventually, somehow, once again…thrive. 

Showing some sympathy for Henry seemed the right thing to do because one thing the twenty-first century has that was lacking in the sixteenth is our knowledge of psychology. By making Henry more self-reflective he is forced to take responsibility for his actions and come to some understanding as to his own emotional prison. We can have sympathy for his plight even if we don’t agree with his choices. Sixteenth century Henry had no psychological framework for his narcissistic life so he dealt with his problems by blaming everyone else for everything, including his own mistakes. 

 
What kind of research did you do in preparation for writing this novel? Where you already familiar with Anne’s story? Do you have any favorite resources, either in the academic or entertainment arenas?

I read all the books about Anne I could find and saw all the movies. I’m not a big fan of the Hollywood films about Anne but, as I said, I did enjoy Showtime’s miniseries, The Tudors. An important source of information was Alison Weir’s books, not just the ones that focus on Anne but everything Weir’s written about the early history of British royals.  Her books are so well researched. There was also a novel, Mademoiselle Boleyn by Robin Maxwell that I really enjoyed and found inspiring. The book focuses on a young Anne Boleyn and her life in the French court. This is where Anne perfected her style and substance. It was the equivalent of going to the best finishing school and the best academic college all combined in one castle. 

This is your fourth book. Was the process or experience of writing Anne of Hollywood different in any way from your previous novels? Do you have a favorite and least favorite part of the writing process?

I love the writing process, even on those days when I’m not feeling particularly creative.  I know that if I keep thinking about the subject I’m working on and keep challenging myself to search for the heart of the matter, eventually I’ll get an idea or inspiration.  It can be quite an adventure.  For some reason I tend to get my best ideas while driving and since I live in California and everyone out here spends a lot of time in their car that works out quite well for me.

As for returning to Hollywood as a setting for this novel, it may seem like I’m exploring the same territory but this time it’s different.  This book is less about Hollywood as a place and more about Hollywood as a state of mind. Maybe the best way to explain it is to say it’s like the movie Chinatown. Though that movie has scenes set in Chinatown, the title really refers to an underbelly side of 1930’s Los Angeles that functioned outside the law and without accountability. In my novel, Hollywood is both a setting and a metaphor for the high stakes game this city is know for—gambling away a more stable future in the (long-shot) hope of fulfilling the big dream. It’s the gamble Anne Boleyn went for when Henry turned his attention her way.  

 
Your previous novels are also set in Los Angeles or Hollywood, and you don’t always paint it in the most flattering light. Is there a particular reason why you like returning to this setting? How much of the contemporary side of the story is based on your real-life experiences?

I actually love L.A. and have great respect for Hollywood but this is not an easy place to survive. Like any center of power and glamour, be it Washington D.C.,  the financial/ arts/social nexus of NYC or  sixteenth century London, …when there are only a small number of spots at the top and a lot of competition for those spots, the game can get rough. On the other hand, this town can be very forgiving. If you manage to have a second act here, no one holds your past mistakes against you the way they might in a snobbier society. 

I also write about this city because I’ve lived and worked here a long time.  I know how Hollywood works and have lots friends who also work in the industry. Since I’m curious and a good listener people like talking to me, sharing their stories and problems. I’m told I give good advice. So I guess being an amateur shrink has given me a lot of material to work with.

The characters in Anne of Hollywood are based on their historical counterparts; was there any one character in particular you enjoyed writing about (or researching)?

Of course I love Anne but turning Thomas Cromwell into Theresa Cromwell was a lot of fun and it made perfect sense. Thomas Cromwell had a coldness about him. He didn’t spend any time getting emotional over who was being sent to the Tower. Though there are plenty of cold-hearted, ambitious guys in L.A., there are also plenty of women with those qualities and I thought a woman was a more modern way to go. Of course these women do have an emotional side but it’s usually kept in check and when they designate another woman as the enemy they are without mercy.  I loved showing Theresa’s duplicitous side. In one of my other novels I make the point that men are born with compartmentalization skills and women are born with manipulation skills. It’s all in the DNA. That said, women who are really good at being duplicitous are usually very charming.  Recently someone in L.A, made a comment about one of these “Theresa Cromwell” type women. He said, “When she’s standing in front of you, you can’t see through her.” Love that line. Wish I’d come up with it. 

The other thing about turning Thomas into Theresa is it gave me a chance to show another dimension to that character. Of course Theresa is obsessed with Henry because he’s her boss and the most attractive, powerful man she’s ever been around, but she’s also obsessed because he factors into her romantic fantasies. She knows he’ll never be interested in her that way but that doesn’t stop her from being highly motivated to get his attention and approval. 
 

In your novel, Anne is a writer who struggles to find her drive and her voice, and only manages to do so after her relationship with Henry has ended. What made you decide to add this side of Anne to the story?  

One of the things that struck me about Anne Boleyn is that she was Henry’s intellectual equal. They shared books and an interest in the political and theological issues of the day. However the sixteenth century didn’t offer smart women a way to parley their intelligence into anything substantial. In a way being a freelance writer these days isn’t that different. It’s hard to make a decent living writing for magazines and blogs. I have so many girlfriends who are really smart, experienced professionals who are struggling to support themselves with this career choice. What’s happened is that having a liberal arts education has become a choice for rich girls looking for husbands and a niche in society.  Poor and middle-class girls may come to the conclusion that they can’t afford to specialize in an area where few decent paying jobs are available. In the sixteenth century, Anne’s arts education, at best, could get her a better husband. Astonishingly, twenty-first century Anne (who is not a royal and not living on a trust fund) discovers that her education can’t offer her that much more. The two Annes are in synch here despite the five hundred years that separate them. 

I also wanted to make that point that there’s now plenty of research that tells us that women who get divorced from powerful men often find their own voice and talent once they’re on their own. Being with an Alpha Male means you are always serving his needs, no matter how much staff and help you may have to assist you. It’s all about him. That’s the way it goes. Though Anne wanted to stay in that marriage once free of it, she can finally use her intelligence, her maturity, and her experience to go out into the world and figure out her next chapter. 
 

Before becoming a novelist, you worked as a screenwriter and wrote a column in Los Angeles Magazine. How have these previous professions influenced your novels? If you weren’t a writer, what would you be doing?

I always say that being a novelist has made be a better screenwriter and being a screenwriter has made me a better novelist. Novel writing teaches you the importance of going deep into a character and developing a point of view. Screenplays teach you how to move a plot along quickly. I guess what I’m shooting for is characters with depth in a fast-paced story. 

If I wasn’t a writer, I can’t imagine what I’d be doing. Maybe something in the field of psychology because I’m fascinated by what drives people to do what they do. I could never be a shrink, though. The kind of intense therapy as seen on shows like HBO’s In Treatment is not for me. I’m more analytical than confrontational and I’m probably not patient enough to be a therapist. I’m very problem/ solution and don’t like dwelling on what happened in the past. My attitude is okay I had a bad childhood, time to get over it, next. 

Who are your writing influences? What are you currently reading?

Like everyone else (it seems) I recently read and enjoyed Jennifer Egan’s A Visit From the Goon Squad. I also recently re-read Bret Easton Ellis’ Imperial Bedrooms. Bret is brilliant at capturing a dark side of L.A.’s culture. Also read New World Monkeys by Nancy Mauro, a smart, darkly comedic piece of work. Next up on my to-read stack of books is something that’s a bit of a departure for me—cowboy noir, The Sisters Brothers, a novel by Patrick DeWitt. Also looking forward to reading Allison Weir’s latest contribution to Tudor history…Mary Boleyn: The Mistress of Kings.

Do you plan to revisit Anne’s world in your next novel (perhaps the life of Elizabeth)? Or are you moving on to an entirely different cast of characters?

I’m still very attached to the characters in this world and I might come back to them at another time.  Exploring a modern day Elizabeth is definitely a real possibility. I’m also contemplating a couple of other ideas, continuing my exploration into relationships between men and women and the eternal challenge: How to make a relationship work with sovereignty over one’s own life and self-esteem intact.