What’s Jewish about “The Princess Bride?” At first glance, the answer might seem “inconceivable”—but as you dig deeper, it’s a delightful rabbit hole of connections. Starting with Billy Crystal’s unforgettable portrayal of Miracle Max, the film has layers of Jewish humor and influence. Add to that the creative genius of author William Goldman and director Rob Reiner and the connections only multiply.
Now, you can revisit the magic at “The Princess Bride: An Inconceivable Evening with Cary Elwes” on March 7 at The Factory in Chesterfield. This special event includes a screening of the iconic film, followed by behind-the-scenes stories from Cary Elwes (Westley himself).
The “rabbit hole” of connections
William Goldman – Author and screenwriter
The original 1973 novel “The Princess Bride” was penned by William Goldman, a Jewish author raised in Highland Park, Ill., by observant Jewish parents. According to his 2018 obituary in the New York Times, the book’s title emerged from a charming family interaction: before a business trip, Goldman asked his two daughters what story they wanted. One requested a tale about a princess, the other about a bride, leading to the combined title.
Rob Reiner – Director
The film’s director, Rob Reiner, is also Jewish. His cultural background has influenced his storytelling approach, contributing to the film’s unique comedic and narrative style. Reiner has spoken extensively about how his Jewish upbringing shaped his sensibilities, particularly his commitment to values like honesty, integrity and education. In a 2017 interview with JTA, Reiner quipped that Jewish humor arises from a history of hardship, stating, “You have Cossacks. You have Hitler. You have to have a sense of humor or you can’t survive.” His comedic chops were honed in a home filled with Yiddish influences and a strong comedic tradition, thanks to his parents, Carl and Estelle Reiner. His Jewish roots even extended into his parenting; during the pandemic, he spoke about “home shuling” with his grandchildren, a humorous twist on homeschooling that reflected his lifelong connection to Jewish tradition.
Mandy Patinkin – Inigo Montoya
Mandy Patinkin, who portrayed Inigo Montoya, was born Mandel Bruce Patinkin in Chicago to a Jewish family. He was raised in a Conservative Jewish household, attending religious school daily and singing in synagogue choirs. For Patinkin, his role in “The Princess Bride” carried profound personal meaning. The iconic line, “I want my father back, you son of a b****,” was a tribute to his late father, Lester Patinkin, who passed away from cancer when Mandy was 18. Mandy later revealed that he channeled his grief into that moment, saying, “In my mind, if I get the six-fingered man, that means I get to kill the cancer that killed my dad.”
Patinkin’s connection to his heritage shines beyond the screen. In a lighter but equally heartwarming moment, he famously performed “Take Me Out to the Ballgame” in Yiddish, blending his love for music and Jewish culture.
Billy Crystal – Miracle Max
Billy Crystal’s portrayal of Miracle Max is unforgettable, even though his character is only onscreen for about five minutes. Crystal packed a half-hour of comedy into those fleeting moments, turning Max into one of the film’s most beloved characters. His performance is legendary and the story of how it came to be is pieced together from interviews, an oral history and Elwes’ own book about the making of the movie, “As You Wish.”
Director Reiner envisioned Miracle Max as a scene-stealing, kvetching character in the tradition of Catskills Jewish humor—much like Mel Brooks’ “2,000 Year Old Man,” co-created with Reiner’s father, Carl. Crystal embraced the role, later saying, “I had relatives like him.”
Over three chaotic days of filming in the cramped set of Max’s hovel, Crystal improvised endlessly, with Reiner giving him near-total creative freedom. According to Elwes, “For three days straight and ten hours a day, Billy improvised 13th-century period jokes, never saying the same thing or the same line twice.” The results were so riotously funny that the cast and crew couldn’t stop laughing, ruining take after take ,and bringing production to a standstill.
Carol Kane – Valerie
Carol Kane’s portrayal of Valerie, Miracle Max’s equally kvetchy and sharp-tongued wife, is a perfect comedic counterpart to Crystal’s performance. A Jewish actress with a knack for playing eccentric, offbeat characters, Kane leaned into the role with her signature blend of warmth and absurdity. Like Crystal, she had deep roots in Jewish humor and the banter between Valerie and Max—filled with bickering and exaggerated exasperation—felt like something straight out of a classic Borscht Belt comedy routine.
The Princess Bride: An Inconceivable Evening With Cary Elwes
Whether you love “The Princess Bride” for the swashbuckling romance or its deeply Jewish humor, it’s more than just a cult classic—it’s a cultural touchstone.
When: March 7 at 8 p.m.
Where: The Factory in Chesterfield, 17105 North Outer 40 Rd, 63005
More Info: You can purchase tickets online.
