Sissy Goodwin Walked Tall

PHOTOGRAPHY by Mel Melcon

The bravest man I ever met lived in Casper, Wyoming. He served in Vietnam, drank beer and played golf on weekends, and rode rodeo as a young buck.

He also wore red dresses and preferred pretty pink bows.

To merely call Sissy Goodwin a cross-dresser, to dismiss him as a troubled soul compelled to wear woman’s clothing, does a disservice to both my dear friend and the English language.

It’s like defining Melville by his whales and Picasso by his paint.

Sure, there was that, there was also more.

Sissy was a rebel.

Today, cross-dressing is still viewed as aberrant behavior even in big cities, but the practice remains almost unthinkable in a sparsely-populated state that in my mind will always be associated with the death of college student Matthew Shepard, who was tortured and killed in 1998 because he was gay.

Still, Sissy persisted. 

In the end, he was stronger than all the cowboys roped together across the entire Cowboy State. He endured a profoundly hostile environment, beaten and belittled by those big strong manly types, those Bubbas in pickup trucks.

One drove up to his house and kicked out his front teeth. They called him a queer and a pervert. He was ordered out of countless stores, hotels and restaurants, all because of the way he dressed.

But Sissy looked the other way, and went on just being him.

He even called himself Sissy, embracing who he was.

What set him apart, he explained, was what he called gender independence.

He just liked to do most things in a dress.

Eventually, even in rural Wyoming, he began to make a difference.

And now he’s gone.

Larry “Sissy” Goodwin died of Stage IV brain cancer earlier this month at age 73. 

I hadn’t spoken with him in years, but he knew how I felt. He knew that meeting him had changed my personal definition of bravery.

Because my man Sis rose above all the macho noise. 

As his wife Vickie recalled, “He was just who the hell he was.”

I met Sissy in 2013 while reporting a story about declining oil fortunes. 

I flew to Casper, looking for young men who laid off from their derrick jobs, had returned to school. On a college campus, I asked you guys if they were former oil workers.

“Not us,” one said, “But go up to the industrial arts building and talk to Sissy.”

So that’s what I did.

At the shop table, he turned around, dressed in pink, engine oil on his hands.

We talked about the story at hand, then addressed what I really wanted to know.

Could I profile him?

Of course I could, he said.

And so I dove into the reporting about this cross-dresser in the Cowboy State, a place known for its big-buckled outdoor ethic and intolerance of alternative lifestyles. 

For most of his life Sissy coped with a compulsion that at times made him cry and embarrassed his family. He’d discovered long ago that he couldn’t stop himself.

Sissy wasn’t gay; he was married for half a century and had two adult children. Born in tiny Douglas, Wyo., he was raised by an alcoholic mother and abusive stepfather.

Secretly dressing up in girls’ clothing offered what he called “a safety valve; an escape from a hostile environment.”

As a young cowboy, he rode bulls bareback, a free spirit who never shied away from a fistfight. 

Yet danger lurked.

When he competed in rodeos, he feared any mishap might land him in a hospital where doctors would discover the women’s panties under his cowboy chaps.

Eventually, he divulged his secret to his soon-to-be wife, Vickie, who already suspected — she’d caught a glimpse of lace beneath his blue jeans.

At first, she took his oddity in stride, but years later would ask herself, “My God, what have I gotten myself into?”

In 1972, Goodwin started to wear blouses and skirts in public. Severely depressed, he concluded that if he wasn’t true to himself, he would eventually end his life.

A defining moment came when doctors helped him understand his cross-dressing. With Vickie’s help, he worked to accept himself. Each morning, standing at a mirror, often weeping, he repeated a mantra: “I am a good person.”

Later, when a woman called him a sissy, he took possession of the insult and assumed the name. “First I was offended. Then I saw it: ‘That’s who and what I am. I wear women’s clothes.’”

But it would not be easy, this life as a rebel in a red dress.

After Sissy was arrested in a department store in 1979 for wearing a dress, Casper police offered to drop the charges if he’d quit cross-dressing in public. Goodwin refused, saying no laws forbid the practice.

He realized a truth about Wyoming. “When someone doesn’t meet their expectations of what a man should be like, they run him out of town,” he said. “I wasn’t going to go.”

Still, it hurt. 

“The physical wounds from a beating eventually heal. But the pain of being shunned by people you know lasts a lifetime. It’s worse than getting kicked in the kidney.”

He knew his decision to live his life hurt his family, his wife and his children.

Son Travis was taunted as the son of “fairy Larry.” Sissy taught him to fight back. “I blame myself now,” Goodwin told me. “He was defending his dad when he didn’t really know what he was defending him for.”

Travis had twice seen his father dressed in men’s clothing, once at his sister’s wedding. “You could see him squirming to get out of that dress shirt and get back into his dress.”

Yet the son came to respect the father.

“He’s the most brilliant man I know,” Travis said. “He’s not just strong physically, but mentally as well. He really is my hero.”

Vickie watched her husband suffer but never quit.

“He felt so alone, as you know, out there in the world, he felt so alone,” she said in Sissy’s obit. “He wanted other people to know so they wouldn’t feel alone, because he learned there were a lot of people that felt like he did.”

At the state fair one year, he was kicked in the butt and turned to face five men in cowboy hats. He eyed his attacker and pointed at his blouse: 

“See that buddy? Don’t let it fool you and don’t let it happen again.”

Finally, progress came.

A stranger once saluted him in public for “having the guts not to be a cookie-cutter cowboy.” Another apologized for driving by his home years ago and shouting a slur.

Friends wrote a song about him and he’d shout the refrain proudly: “A cowboy in a party dress just ain’t right.”

One day, I accompanied Sissy to a local mall, where he was on the hunt for an industrial-sized wrench and two special somethings: colored hair bows and a pretty new dress — preferably red, size 12.

He was a linebacker-sized figure in a pink skirt, lacy yellow blouse and five-o’clock shadow; a gold lamé purse slung over his shoulder and a white bow affixed to his receding gray hair.

“Boy, you’re cute,” says a middle-aged woman, who then laughed derisively.

In a hardware store, a man shook his head in disgust. 

Another asked, “Is it a prank? A joke?”

But Sissy looked straight ahead, ignoring the stares and the catcalls.

Back in the car, the object of such scorn put on pink sunglasses adorned with a tiny red plastic bow. “I got them in Reno,” he said. “Aren’t they cool?”

Later, rummaging through dresses at a Goodwill store, he admitted that his fashion sense was stuck in the 1950s. “You know you’re out of date when you buy your clothes from the Halloween rack,” he joked.

Until he retired, he went to work in the male-dominated world of Casper College’s power technology lab, where he taught young men in farm hats the science behind heavy machinery.

He packed his lunch in a pink Playmate cooler and carried his coffee in a green thermos with Wyoming’s logo of a bronco-riding cowboy.

After his family, the people who the most to Sissy were his students.

He asked classes not to judge him by his dress, and they responded.

And they did it in a big, heart-breaking way.

One day, in a synchronized show of respect and acceptance, they removed their hoodies to reveal pink hair ribbons and matching pink shirts. 

Sissy nearly wept at the gesture.

Like I’m weeping now, just at the thought of it.

See ya, Sis. Go ride that bucking bronco. 

Because you were the truest, tallest-standing cowboy of them all.


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