Sashaying Through Time: The History of Drag

Juno Bennett
Exploring Echoes
Published in
10 min readOct 30, 2023

The rich history and cultural significance of drag unfolds from its roots in Ancient Greece to its modern mainstream influence. Through key moments and figures, drag’s transformative power as a medium for self-expression, activism, and change is vividly showcased.

Photo by Quino Al on Unsplash

A quote often attributed to Oscar Wilde rings especially true in the fabulous world of drag: “Give a man a mask, and he will show you his true face.” Bold, daring, and unapologetic, drag has served as a transformative art form and a powerful means of self-expression throughout the ages. Let’s sashay our way through the annals of history to explore the origins and evolution of drag.

But first, what is drag? Put, drag is the art of dressing and performing in the clothing and mannerisms typically associated with the opposite gender. Drag queens, usually male performers dressing as women, and drag kings, female performers dressing as men, have long captivated audiences with their over-the-top costumes, makeup, and personas. While drag is often associated with the LGBTQ+ community, it has a long, complex history transcending any single group or culture.

Picture it: Ancient Greece, 5th century BC. A playwright named Aristophanes is putting the finishing touches on his latest comedy, “Lysistrata.” In this play, women of Athens, tired of the ongoing war, decide to withhold sex from their husbands until peace is achieved. There’s just one problem — female actors are nowhere to be found. In a stroke of ingenious, gender-bending creativity, Aristophanes dresses male actors in female attire, and the theatre world is forever changed.

This historical anecdote reminds us that the roots of drag run deep, extending far beyond what we might typically associate with the term today. With that in mind, join us as we delve into the fascinating and diverse history of drag, celebrating the trailblazers who pushed boundaries, challenged societal norms, and paved the way for future generations to live their most fabulous lives.

Sashaying Through the Sands of Time: Drag’s Ancient Roots (Pre-17th Century)

Our glamorous journey begins in the land of philosophers, gods, and togas — Ancient Greece. As previously mentioned, male actors often portrayed female characters in Greek theatre. This cross-dressing practice, known as “πρωτον τραγωδία” or “proton tragodia,” involved donning wigs, masks, and padded costumes to emulate feminine features. Talk about the OG contouring!

One remarkable anecdote from this period involves Phrynichus, a 5th-century BC Greek tragedian. In his play “The Fall of Miletus,” Phrynichus broke the hearts of Athenians with his depiction of the city’s capture. The female characters’ emotional performances, brought to life by male actors in drag, were so moving that the Athenian audience wept openly. Clearly, the power of drag to evoke deep emotions is nothing new.

As we venture eastward, we find the rise of Japan’s vibrant Kabuki theatre in the 17th century. At its inception, both male and female performers graced the stage. However, due to concerns over the moral character of actresses, women were eventually banned from performing. Enter the onnagata — male actors who specialized in female roles. They mastered the art of transforming themselves into women through elaborate makeup, wigs, and costumes, creating an ethereal, almost divine illusion.

One legendary onnagata, Yoshizawa Ayame, was so convincing in his female portrayal that a nobleman, smitten by his performance, even offered to buy out his contract. Despite the generous proposal, Ayame remained on stage, proving that a true queen knows her worth.

In 16th-century England, we find another example of drag’s ancient roots. With women prohibited from performing in public theatres, all-male troupes took the stage, portraying both male and female characters. Notably, William Shakespeare’s famous works featured numerous cross-dressing roles, such as Viola in “Twelfth Night” and Rosalind in “As You Like It.” With a flair for the dramatic, Shakespeare introduced his audiences to the first taste of drag’s transformative powers.

Thanks to these trailblazing moments, drag has continued evolving, shape-shifting, and dazzling audiences across time and cultures. So, hold on to your wigs because our journey is only just beginning!

Can I Get an Encore? Drag in the 19th and Early 20th Century.

Fast-forward to the 19th and early 20th centuries, when the limelight shone on vaudeville and burlesque shows in the United States and Europe. These theatrical spectacles showcased a variety of acts, from jugglers to comedians, but none captured the audience’s imagination quite like the female impersonators and gender-bending performers.

One such star, Julian Eltinge, dazzled the world with his glamorous portrayals of women. Known as the “greatest female impersonator of all time,” Eltinge’s performances were so mesmerizing that he starred in his Broadway show, “The Fascinating Widow.” Legend has it that after a stunning performance, an audience member remarked, “My, ain’t she the handsome woman!” Little did they know, “she” was indeed a he!

As the Roaring Twenties gave way to the Great Depression, underground drag clubs flourished in cities like New York, Berlin, and Paris. Amidst economic turmoil, these clubs provided a safe space for LGBTQ+ individuals to express themselves, connect with like-minded people, and enjoy a night of fabulous entertainment.

The Pansy Craze, as it was called, saw the rise of legendary drag performers like Jean Malin, who pioneered the art of “insult comedy.” Malin’s sharp wit and biting humor earned him a devoted following, and he soon became a fixture on the Hollywood party circuit. Malin’s antics were so outrageous that, during one soiree, he famously tossed Hollywood starlet Tallulah Bankhead into a swimming pool after she dared to upstage him. What is the moral of the story? Never try to out-diva a drag queen!

This vibrant period of drag history ultimately left a lasting impact on mainstream entertainment as drag performers began crossing over into film, music, and theatre. But as we’ll soon see, drag’s journey through the annals of time was far from over. Honey, we’re just getting started!

When Sequins Meet the Struggle: Drag in the Mid-20th Century (1940s-1960s)

Post-World War II, America saw a flourishing gay subculture; with it, drag families and houses rose. These tight-knit groups of performers provided support, camaraderie, and mentorship to one another while also fiercely competing in drag balls and pageants. As the legendary drag queen Dorian Corey once said, “If you can’t love yourself, how in the hell are you gonna love somebody else?”

One memorable anecdote involves the legendary drag queen and activist Flawless Sabrina. In 1959, she organized a national drag pageant, later documented in the groundbreaking 1968 film “The Queen.” The pageant, held at New York City’s Town Hall, was a pioneering event showcasing the immense talent and charisma of drag performers across the country.

As the Civil Rights Movement gained momentum, drag queens played a crucial role in advocating for LGBTQ+ rights. In a time when being openly gay was still a risky endeavor, drag queens were unapologetically visible and proudly defiant.

One pivotal moment occurred during the Compton’s Cafeteria Riot in San Francisco in 1966. When a police officer attempted to arrest a drag queen, she threw her coffee in his face, sparking a riot that would later be seen as a precursor to the more well-known Stonewall Riots in 1969.

Speaking of Stonewall, drag queens were front and center during that historic event. Famously, Marsha P. Johnson, a transgender woman and drag queen, is said to have thrown the first brick or shot glass (accounts vary) that ignited the riot. The bravery and resilience of these queens in the face of adversity remind us of the importance of drag as an art form and a vehicle for change.

As we’ll see in the next chapter of our fabulous journey, drag’s impact would only grow as it entered the mainstream and helped shape the cultural landscape in the decades to come. So, buckle up, darling, and prepare to be dazzled!

Disco, Drag Balls, and Defying the Odds: Drag in the Late 20th Century (1970s-1990s)

As disco fever swept the nation in the 1970s, drag balls took center stage in New York City’s underground LGBTQ+ scene. Performers competed in categories like “Realness,” “Face,” and “Voguing,” vying for trophies, glory, and the title of “Legendary.” These balls were immortalized in the iconic 1990 documentary “Paris Is Burning,” which introduced the world to the ballroom scene’s glitz, glamour, and fierce competition.

One unforgettable ballroom anecdote involves the legendary drag queen Pepper LaBeija, who, during a heated face-off with her rival, Crystal LaBeija, famously declared, “I don’t say she’s not beautiful, but she wasn’t looking beautiful tonight!” Pepper cemented her place in drag ball history with a single, sassy quip.

The 1980s and 1990s saw the devastating impact of the AIDS crisis on the LGBTQ+ community. Amidst fear and uncertainty, drag queens became powerful forces for change, raising funds and awareness for HIV/AIDS research and support services.

One such queen was the incomparable Lady Bunny, who, in 1987, organized the first-ever Wigstock festival in New York City. This annual drag extravaganza drew thousands of attendees and raised vital funds for AIDS-related causes. Lady Bunny’s tenacity and commitment to her community serve as a testament to the power of drag as a vehicle for activism and change.

As the 20th century drew to a close, drag’s influence on mainstream culture continued to grow, with performers like RuPaul and Divine captivating audiences worldwide. And, as we’ll see in the next chapter of our journey, the new millennium will only bring more opportunities for drag to dazzle, delight, and challenge the status quo. So, hold on to your lashes because things will get even more fabulous!

Slaying the Mainstream: Drag in the 21st Century

The 21st century has seen drag catapulted into the mainstream like never before, with TV shows like “RuPaul’s Drag Race” becoming cultural phenomenons. RuPaul once said, “We’re all born naked, and the rest is drag.” This sentiment perfectly captures the universal appeal of drag as an art form that transcends boundaries and speaks to the human experience.

One heartwarming anecdote comes from the show itself. In season 5, contestant Roxxxy Andrews famously broke down in tears while discussing her abandonment at a bus stop as a child. Her fellow competitors rallied around her with the now-iconic quote, “We’re all a family here,” a powerful reminder of the resilience, love, and unity that drag can foster.

Today’s fashion and beauty industries are undeniably influenced by drag. From bold makeup trends like contouring and overlined lips to avant-garde clothing designs, drag’s impact on the world of style is unmistakable. Designers like Alexander McQueen and Marc Jacobs have drawn inspiration from drag culture, showcasing the art form’s far-reaching influence.

As drag becomes more mainstream, it also serves as a platform for discussing and addressing critical LGBTQ+ issues in the United States. Performers use their visibility and influence to advocate for equal rights, raise awareness about hate crimes, and promote acceptance and understanding.

However, the drag community also faces challenges, including concerns about inclusivity and representation. As more diverse performers, such as transgender and non-binary queens, enter the spotlight, it’s essential to recognize and address the unique experiences and needs of all members of the drag community.

Drag has come a long way since its ancient roots, evolving into a powerful cultural force that continues to inspire, entertain, and challenge societal norms. As we look to the future, one thing is certain: drag’s fabulous journey is far from over. So, as we sashay into the unknown, let’s celebrate the beauty, the bravery, and the unapologetic fierceness of drag. Can I get an amen?

The Future of Fierceness: Drag’s Next Act

As we strut into the future, drag is adapting and evolving like never before, embracing the power of technology to reach new heights of fabulousness. From virtual drag shows to social media sensations, the digital age has given rise to a new generation of drag superstars.

Consider the curious case of Miss Fame, a queen who rose to prominence through her mesmerizing YouTube makeup tutorials. By demonstrating her skills and artistry online, Miss Fame caught the eye of the drag world and went on to compete in season 7 of “RuPaul’s Drag Race.” Today, she’s a bona fide drag icon, gracing red carpets and collaborating with major beauty brands. It just goes to show that in today’s world, there’s more than one way to snatch a crown!

As drag continues to push the boundaries of gender, art, and performance, we can expect to see even more groundbreaking moments in the years to come. From bio queens and drag kings to genderqueer and non-binary performers, the drag landscape is becoming more diverse and inclusive.

One trailblazing example is the rise of Laganja Estranja, a fierce queen who made history as the first drag queen to perform on a major TV dance competition show. As she danced her heart out on “So You Think You Can Dance,” Laganja proved that drag’s potential is limitless. Moments like these remind us that the future of drag is brighter, bolder, and more beautiful than we could ever imagine.

So, my darlings, as we leave our fabulous journey through the history of drag, remember to keep your heels high, your wigs snatched, and your spirits even higher. Because, after all, the future of fierceness is in our (perfectly manicured) hands!

Have you ever watched the movie “To Wong Foo, Thanks for Everything! Julie Newmar”? How do you think it contributed to the mainstream understanding and appreciation of drag? Share your thoughts, and let’s dive into a discussion about its impact!

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Juno Bennett
Exploring Echoes

Exploring festivals & global food tales, spotlighting eras that reshaped us. Served with a modern twist for the curious.