The fun and frivolous turn-of-the-century Billboard Hot 100 hit song found its roots in gender-bending and drag.

On the surface, Shania Twain’s 1999 hit “Man! I Feel Like a Woman!” is the ultimate girl power anthem. With lyrics like “No inhibitions, make no conditions / Get a little outta line / I ain’t gonna act politically correct / I only want to have a good time / The best thing about being a woman is the prerogative to have a little fun,” it’s all about letting loose for a no hold’s bar night on the town.

But the actual inspiration behind the song? Crossdressers.

Twain has said the hit, which she co-wrote with producer-turned-ex-husband Robert John “Mutt” Lange, from her 1997 album Come On Over, was likely inspired by nights out at gay clubs with her friends during her teen years. And it’s no wonder that today, it’s become as popular with drag queens as it has with audiences of every kind.

Twain had a 'fascination' with 'men transforming themselves into beautiful women'

Although she had been writing songs since she was 10, when Twain was 18, she moved to Toronto to focus on a music career. “If I was to achieve my long-term goal of making music for a living, this is where I needed to be,” she wrote in her 2011 autobiography From This Moment On.

She shared a one-bedroom apartment with two girlfriends who were both going to college in the Ontario capital. “Had I lived by myself at 18, I might have become a hermit,” she wrote in the book. “Fortunately, my roomies, while hardly party girls, were sociable and introduced me to new, interesting friends from school.”

One such friend was Sheriff, a “flamboyant guy from Trinidad.” On Friday nights, the girls often went out to gay bars with him and his friends. “They’d come over to our place first, and we’d all dress up and put on dark eyeliner — the guys included,” she continued in the book. “Madonna had just hit it big, and everyone was copying her look. We’d dress like her, back-comb our hair until it was too big and all spiky, then head out on the town.”

For a small-town girl from Timmins, the experience was eye-opening. “This was an adventure for me, as it was all new,” she wrote. “Gay bars had the best dance music and the most impressive dancers....Being inexperienced at applying makeup, I marveled at how artistic and glamorous some of the men were. They looked so gorgeous, with features that had been defined and exaggerated with blushes, liners, shadows and accessories.”

And apparently that impressed her much. “My fascination with this initial introduction to men transforming themselves into beautiful women likely sowed the seed of inspiration for a song I would write years later: ‘Man! I Feel Like a Woman!’” she revealed in her book.

Shania Twain's Man, I Feel Like a Woman music video

Shania Twain's "Man, I Feel Like a Woman" music video

A local gig opened her eyes to the world of performance and drag

While she was discovering new worlds and honing her craft, an unthinkable tragedy happened when she was 21: Her mother, Sharon, and stepfather, Jerry, were killed in a car accident.

“I was just going to give up music,” Twain told Country Weekly in 1995. “I thought, my family comes first. I have to take care of them. I didn’t even think of the future.”

As fate would have it, taking care of her younger siblings Carrie-Ann, Darryl and Mark, came in the form of a performing job at Deerhurst Resort in Huntsville, Ontario. “I’m lucky I got the job at Deerhurst because it was music,” she continued.

Not only did the job keep her on track, but it also introduced her to the world of showmanship. “Deerhurst was the first time I was directed on stage and it was the first time I had dancers. It educated me,” she told the Canadian publication Macleans in 2015.

“When it was time to put together my show in Vegas, all that dazzle wasn’t foreign to me. I was familiar with the whole feel of a big stage show because of my being there,” she said of the resort. “It was like a mini-Vegas! Or like attending a Vegas performing arts school.”

Some sources report that her exposure to drag performers during her time there also contributed to the influences of “Man! I Feel Like a Woman!”

Twain believes the song brings people together

Twain’s early influences from her Toronto club days and her Vegas-like training likely all combined to bring the frivolous fun to “Man! I Feel Like a Woman!” which extends its wide appeal to every genre. Rolling Stone even called the music video, in which Twain dresses up in a menswear-inspired look, complete with a top hat, “stereotypically male and indulgently female.” And, like in her early gay club days, the men in the video don perfect eyeliner.

“A lot of straight men sing ‘Man! I Feel Like a Woman!’ just for the sheer entertainment of it,” she said in a 2017 interview with PrideSource. “I think songs like that have been great, maybe, contributors to bringing us together, if not for anything than just for the common denominator of music and owning that for whatever it means to them — and that breaks down barriers.”

In fact, that’s what Twain relies on when she’s performing songs that she’s written like this — appealing to the love of music over anything that could spark controversy. “I like to have a sense of humor about everything, especially things that can have a lot of tension,” she continued. “A song like ‘Man! I Feel Like a Woman!’ just smacks it dead for me. The audience issue is not something I worry about. I’m respectful to my audience and I appreciate them for relating to my music regardless of their point of view on whatever it is, whether it’s politics or social issues. I’m not here to judge.”

Shania Twain's "Man, I Feel Like a Woman" music video

Shania Twain's "Man, I Feel Like a Woman" music video

Twain believes 'entertainment doesn't have a gender'

No matter her original intention, Twain has become an idol, especially in the drag queen community.

The first time she came across a drag performer dressed as herself was at a Las Vegas imposter show. “It was incredible,” she said. “The country world...might be more conservative, but it’s funny, three of the artists that were in the show were myself, Reba McEntire and Dolly Parton. I thought that was so wonderful… Any artist that is, on a visual level, very expressive would make a great imposter night subject.”

And it’s that gender-bending which she appreciates. “Entertainment doesn’t have a gender. The fashions that ended up stringing together my career — especially the epic, iconic looks — [go] both ways,” she told Macleans. “It can be drag queen-y as easily as it can be a sophisticated woman. We created a seamless, natural place for all of us.”

In fact, she even proudly doles out advice for drag performers who want to mimic her style. As she told PrideSource, the essential ingredients are: “Something leopard print, and I would say a top hat. The boots, for sure!”