Book Club Questions for Chasing Hollywood by Gerry Rich
Book club questions for Chasing Hollywood by Gerry Rich take a closer look at this dynamic memoir about one man’s journey in Hollywood. For more about the book, check out my review first. Chasing Hollywood releases on October 13th.
Wow, Chasing Hollywood is without a doubt one of the most vivid memoirs I’ve ever read. I don’t think I’ve read one that makes you feel like you’re right there with the individual. Chasing Hollywood is so honest, real, and full of humility. Gerry’s career is remarkable.
I love the start in St. Louis and his journey to Hollywood. And of course, all the behind-the-scenes looks at marketing these films were exciting and so interesting.
Five stars all around for this one. Be sure to check out my interview with Gerry for more insight into his memoir, his thoughts on book-to-film adaptations, plus he details what it was like to record his own audiobook.
Book Club Questions for Chasing Hollywood
- What are some of the most memorable movie marketing campaigns for you? Was it a trailer, poster, commercial? Let’s detail why these campaigns have stayed with us.
- Gerry starts off his memoir detailing the marketing work behind the Miramax film, The Crying Game, before going back to his childhood in St. Louis. Why do you think Gerry started his book with the breakthrough marketing strategy on that film? What lessons did he learn from it that he carried on to his other jobs?
- We go back to St. Louis where Gerry, as a child, dreams of something bigger. Movies were his escape, and he vowed to one day work in movies. Why was marketing movies the right career choice for Gerry? Have you ever felt similarly, that you aspired for something bigger in your life and career?
- Gerry describes his love for movies growing up, including many of the films that left a lasting mark. What are some of your favorite movies, and why are these ones so important to you?
- Gerry’s career arc is quite impressive, going from humble beginnings in St. Louis to being a marketing executive at Columbia Pictures, DeLaurentis Entertainment Group, Miramax, Miramax/Disney, MGM, Paramount, and MGM/United Artists. What are some of his stories about working in Hollywood that stuck with you?
- He detailed the marketing of so many popular films. Which marketing campaigns were you most engaged with learning more about?
- Each chapter covers a significant time in his career, and also personal life, with insights learned along the way. What were your key takeaways from these insights?
- It seems that while it was the most toxic workplace, Gerry did learn a lot during his time at Miramax. Have you ever had a tough work experience that, where looking back, you realized you learned valuable lessons?
- The acquisitions by tech companies have left Hollywood in uncharted waters. While audiences crave original content, studios are still pumping out sequels and more superhero stories. But Gerry describes how the summer of 2026 was an impactful one with breakout hits from indie films. Where do you see the future of movies?
- If they turn his memoir into a movie or series, who should play Gerry and the other key roles?
Additional Recommendations
Hope you enjoyed the book club questions for Chasing Hollywood! Here is a recommendation along with a link to book club questions.
Gerry mentions how the success of book-to-film adaptations like Project Hail Mary is a great thing for movies. So if you haven’t read the book yet, now is a good time! Even if you have already seen the movie, I still highly recommend the book.
Project Hail Mary is an enjoyable novel about a man’s journey to save the human race. It’s also about an unlikely friendship. Honestly, sometimes it’s too heavy on science details for me, but I still liked it quite a bit. Check out my review here. And my book club questions here.
Happy reading!
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