The golden age of Hollywood and the magic of “The Wizard of Oz” continue to fascinate audiences decades later. For residents of Muskegon, Michigan, that enchantment held a special connection to their community through Danny Windsor. This beloved entertainer, who passed away at 86, is fondly remembered not only for his vibrant personality and drag performances but also for his small yet iconic role: one of the flying monkeys in the classic 1939 film, “The Wizard of Oz.”
Danny Windsor’s journey to the Emerald City began in his adolescence. While his time on screen as a winged monkey was brief, it became an enduring part of his legacy, a unique chapter in a life filled with showmanship and community spirit. His passing on Saturday marked the end of an era for Muskegon, leaving behind a legacy woven with laughter, performance, and a touch of Hollywood magic.
Those who knew Danny Windsor in Muskegon attest to his unforgettable presence. “You would be hard pressed to find anybody in Muskegon who didn’t know him,” shared Debra Brown Hendrickson, a close friend and the executor of his will. Their friendship blossomed in the mid-1990s at a local bookstore event celebrating the centennial of L. Frank Baum’s “The Wizard of Oz,” a serendipitous beginning sparked by the very film that would forever link Windsor to cinematic history.
The story of how Danny Windsor joined the cast of “The Wizard of Oz” is a classic Hollywood tale of chance and opportunity. Working on another production on the MGM lot in 1939, young Windsor found himself unexpectedly summoned to the set of “The Wizard of Oz.” As Hendrickson recounted, the production needed someone who could fit into the flying monkey costume after one of the actors was unable to perform. “They put him in the harness because he could fit in it, that’s what he always told me,” she explained.
Windsor’s stint as a flying monkey was short, just three days of filming. He appeared as one of the menacing winged creatures who capture Dorothy’s dog, Toto, in the forest – a memorable and slightly terrifying scene for generations of viewers. In a 2007 onstage interview with friend Ron Gossett, Windsor humorously clarified some embellished versions of his involvement. “Somehow it got reported that I was the monkey who flew away with Toto,” Windsor said, setting the record straight with a chuckle, “Really, there were several of us.” While he may not have been the monkey solely responsible for Toto’s capture, he was undoubtedly one of the actors who brought these iconic characters to life.
Born in Santa Barbara, California, during the vibrant Roaring Twenties, Danny Windsor was immersed in the world of entertainment from a young age. His parents were vaudeville performers, and he quickly followed in their footsteps. By the time he was a child, Windsor was a contract player and dancer for MGM, nurtured by his grandmother from the age of 10. He was just 13 years old when he donned the flying monkey costume, a testament to his early start in show business.
The Flying Monkeys themselves are an integral part of the “Wizard of Oz” narrative. These winged primates, servants of the Wicked Witch of the West, are among the film’s most visually striking and frightening creations. Their role is pivotal, carrying out the Witch’s bidding and creating obstacles for Dorothy and her companions on their journey to Oz. While Danny Windsor was one of the performers behind the mask, the collective portrayal of the Flying Monkeys contributed significantly to the film’s enduring impact.
When World War II broke out in the 1940s, Windsor traded the stage for service, joining the military and being stationed in Guam. Even in the armed forces, his entertainer spirit shone through as he performed comedy shows for fellow soldiers. After his military service, Windsor returned to his performing roots, creating a vaudeville act called “Doodles and Spider” with a friend. This show, featuring comedy, song, and dance, took him across North America, performing in major entertainment hubs like Atlantic City, New York, Las Vegas, Los Angeles, and Toronto, often opening for well-known headliners.
In the 1960s, Windsor’s career path led him to Muskegon to perform at Northway Lanes, a venue that once hosted nationally recognized entertainers. He found a connection with the area, and Muskegon became his adopted home. While he charmed audiences with various impersonations throughout his career, his Ethel Merman impersonation was particularly renowned and beloved. Starting in the 1970s and continuing into his early 80s, Windsor’s drag performances, featuring Merman and other iconic showbiz women like Dorothy Squires and Totie Fields, alongside his original character “Disco Dolly,” became a staple in the Muskegon entertainment scene. “He did that act quite frequently in Muskegon over the years,” Hendrickson recalled.
Beyond his stage persona, Danny Windsor was known for his warmth and generosity. For 13 years before a stroke in 2009 led to his move to a nursing home, he worked as a greeter at Meijer, showcasing his innate hospitality. He was also a gracious host and an excellent cook, famous for his legendary salsa. Windsor’s generosity extended beyond dinner parties; he regularly shared his homemade food with people throughout Muskegon, from postal workers to bank tellers and even the staff at The Muskegon Chronicle.
Despite a long and varied career in show business, including performances alongside Betsy Palmer in A.R. Gurney’s “Love Letters,” it was his fleeting role as a flying monkey that remained his most recognized credit. “The Wizard of Oz” fans from around the globe regularly sent him requests for autographs. “People mailed him requests weekly from all over the world asking him to sign something from ‘The Wizard of Oz,’” Hendrickson noted, marveling at the film’s enduring phenomenon.
Danny Windsor’s life was a rich tapestry of performance, kindness, and community involvement. While he may have been one of many actors who played the flying monkeys in “The Wizard of Oz,” for Muskegon, he was a singular figure who brought a touch of Hollywood sparkle to their town. “He was just a presence in this town and he brought a little bit of showbiz to Muskegon,” Hendrickson fondly remembered. His legacy extends beyond the silver screen to the countless lives he touched with his talent, generosity, and vibrant spirit.
