Oakland’s Own Cowboy on Black Musicians and Settlers in the Wild West

The Cowboy knows how to perform. When I first saw Wilbert Freeman McAlister at Eli’s Mile High Club in Oakland, he sang the blues. He swayed from side to side, moved his hips, and kicked his feet to his band’s beat. Microphone in hand, he danced back and forth along the edge of the small stage, freestyling the lyrics. His voice was deep and old and mesmerizing. The whole bar leaned in toward him, matching his energy, his rhythm. It was impossible not to. 

He performed in a baby blue Old West shirt, fringe across the breast. High-waisted blue jeans cinched with a big gold belt buckle and white cowboy boots. A tall shiny hat crowned his head.

A week later, climbing the wide stairs of the Defemfry Street Recreation Center in West Oakland, he moved as if still dancing to a song. The cowboy hat still sat high on his curly silver hair. 

 He greeted me with a smile and a polite handshake and before I could even begin to ask questions he took me through the front door and into the Recreation Center, a converted Victorian house. 

A woman greeted us. “Hello Mr. President!” 

He leaned against the wall. “You know who I am?”

“Of course I do, You’re the Cowboy.”

McAlister, better known as The Cowboy, is a singer, dancer, landlord and President of the Oakland Black Cowboys Association. He is 81 years old, from Modesto, California, ​​an agricultural stronghold deep in the Central Valley. He has lived in Oakland since leaving the Military in 1965.  “I am a California boy, born and raised. No one ever guesses with me talking. They all think I’m from the South,” he drawls.

”I found out my roots were from down there, it’s in my blood.” 

He says that his mom is from Texas. “Same thing with my attire. I never thought about wearing cowboy boots. I never thought about wearing a buckle.

When I grew up we called that ‘White boy shit,’ That was what we were taught.” 

“’I started wearing a cowboy hat when I was about thirty. A friend of mine had one, we used to chop cotton together, pick grapes together, and we talked that same talk, but then he started wearing a cowboy hat. I said ‘Boy lemme put it on,’ and I saw how good I looked.”

 “I didn’t want to give that hat back.” 

“When I started wearing it, one of my older uncles stoppe

d me, and said ’you look just like your grandpa,’ and I thought, ‘What you mean I look just like my grandpa? But later I found out he was a rancher. That’s what we called them, not cowboys,but ranchies and ranchers.” 

White history erased Black People from the lore and image of the American West and Country music. When we think of Black migration after the Civil War, we think of moving from the South to Chicago, not to the West. But during the Mexican-American War, many Texan slaveholders used their slaves to move cattle farther westward. After the Civil War, being a cowhand was one of the first paying jobs open to Black men. In big box Western movies, books, and music, Black people are rarely represented. And a substantial percent of working Cowboys were black. There is an Old West story that needs to be told, and the Cowboy makes sure I know it. 

He explains to me that the word ‘cowboy’ orginated from slavery. It was originally a demeaning term for slaves tasked with taking care of livestock. “Most people never know it’s a slave term, but we wear it with pride. There are many of us in California, but here I work with the Oakland Black Cowboys.” 

According to their website, the local nonprofit has,“spent four and half decades enlightening children and adults with the contributions of people of color in the settling of the West.” They have an annual parade, educate children through school visits, and work with local businesses and organizations. The Cowboy is the president and got the organization their official 501 c-3 certification a few years ago. 

But when I first saw Wilbert, I did not see him riding a horse or at a school, I saw him playing music at a bar. He was singing old country and blues. As soon as I asked him about music, he started singing. With his deep, mesmerizing voice he sang Hank Williams, switched to Ray Charles, and then started belting “All My Exes Live in Texas.”

“I always did like country music,” Mcalister explains. “I used to sing one [a song] way back in Elementary, “She’ll be Coming Around the Mountain”.” Mcalister’s face brightens when he talks about performing; it’s what he loves to do. His love for country music goes way back.  

“Have you heard of the Grand Ole Opry Down South?” He asked me.“The Grand Opry theater is a theater where all the white country singers go to perform, the big brand country singers. For a long time they didn’t allow Black singers, but now it’s open.’

‘I went there when I was kid, and this girl took me. I sat in about the fifth row, and sitting there I said, ‘look at my black-ass,’ I was the only black guy there. Charley Pride was performing that night.” 

Stemming from racism against black cowboys in the American west, and a lack of representation now, Black people are far from well represented in country music. It is not because Black country singers did not exist or were not as numerous.Why did Billboard take Lil Nas X’s song Old Town Road off the country music charts? It has banjo, mandolin, twang, all the elements associated with the country genre. Racism in the entire music industry has dampened the voices of Black country singers in mass media. Early on, Black country was separated from country by record labels as ‘Race Music.’The banjo evolved from a three-stringed West African instrument known as the akonting, yet many people associate banjo and bluegrass with white Appalachians. Country music is embedded in Black history. 

The Cowboy is all about history, knowing who did what and when and why. When I first arrived at the Defremery street recreation center the first thing he did was take me inside to see  the history of the house.  

Leaning elegantly against the wall of the house he tells me, “Demfremery’s house, was a white man’s house. He was a well to do man, and he married a black woman. And they donated it to the city of Oakland. It’s a history, it’s a small history, but you know it’s important.”

He then told me about his own experience moving to Oakland after the Vietnam War, “they put us in what they called harbor homes, you colored folk

s stay over there. After WWII blacks started moving out to Oakland, but you couldn’t live in East Oakland, couldn’t live in Piedmont, oh hell no, and you couldn’t even live in North Oakland. You stayed over there, West Oakland, under control.”

 The Cowboy loves performing, but he equally values history and community. He said everything with umph, with a passion for educating. He quizzed me on old singers, singing Ray Charles, Hank Williams, James Brown, mocking me when I couldn’t get all the songs right.

“Oh you got to know that one!” 

But he also told me that I should know the history of Oakland, and that Cowboy comes from a slave term. The Cowboy told me to dig deeper than what I am taught in school, to listen to more music, to read into the history of anything I find interesting. He taught me that because I know and love Hank Williams, I should know Ray Charlies or Big Bill Broonzy just as well. That I should associate the Wild West and the metallic banjo twang of Country with Black cowboys as much as white. 

“I do love doing things for the community, educating kids and people, it’s part of me. As Americans, we should know the history, and I like showing it” he told me.  

The Cowboy plays blues and country some Monday nights at Eli’s Mile High Club in Oakland. There is a yearly Black Cowboy parade outside the Defremery Street Recreation Center in West Oakland, the next one will be in Fall of 2022.