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On a recent Saturday a little past noon, Jennifer Hernandez sat at the dining table in the South Gate home where she grew up. She focused intently, holding a handheld makeup mirror as she used liquid eyeliner to perfect black triangular lines that resembled a compass framing her eyes.
“When you start doing the lines, if they’re not precise, you’ll end up with a really crazy-looking clown,” she explained.
For over five years, Hernandez, a 35-year-old makeup artist and model, has been using makeup to transform herself into a real-life chola clown and documenting it on Instagram, where she has amassed more than 46,000 followers. It’s a labor of love for an image that resonated with her since she was a fourth-grader and noticed it on the tattoos of teaching assistants at school.
“It’s all about real L.A. and I want to share that,” she said.
From spray-painted walls to fine-inked tattoos to drawings on prison envelopes sent from fathers to their kids, the cholo clown has for more than a half-century been deeply tied to L.A.’s Chicano culture. Now it is speaking to a new generation on the pages of social media influencers such as Hernandez, in online ads, TikTok videos and officially licensed MLB masks designed by Mister Cartoon for teams across the country.
Tattoo artist Freddy Negrete helped launch the trend that would eventually become inextricably tied to the cholo clown in 1974, when he was 18 and locked up in juvenile hall for a gang-related shooting. At the time, Negrete was a member of San Gabriel’s La Sangra gang.
Sitting in his cell, he thought of the phrase “Smile Now, Cry Later” from the 1966 song by the soul group Sunny & the Sunliners, and the image of opposing masks — one smiling, one crying — came to him.
“I first thought of these theater masks and how they can represent comedy, tragedy, drama and then the song,” he said. “So I drew the mask, wrote, “Smile Now, Cry Later,” and then mailed out the drawings to people I knew.”
Soon, Negrete began to get requests from fellow inmates who wanted it tattooed on their arms, legs, backs or anywhere they could make space for it.
Over time the theater masks have evolved and been adopted by others. Some artists draw clown faces on the masks with teardrops falling from their eyes — an image that, in addition to “Smile Now, Cry Later,” is often also linked with another ‘60s soul song, “The Tears of a Clown.” The theater masks and the cholo clown are not exactly the same but play off each other, Negrete said.
“When you think about ‘Smile Now, Cry Later,’ and these theater masks, they’re these two sides of this tragic comedy. Just like how the clown face is also coming out of the prison,” said Denise Sandoval, a professor of Chicana and Chicano studies at Cal State Northridge, whose research is focused on lowrider and cholo culture.
The masks spoke to the reality of young Chicano men growing up in L.A. in the 1970s and ‘80s, for some of whom gang life had become a way to form community and embrace a counterculture against one that had long marginalized them, Sandoval said.
It became a way “to sort of hide their emotions and kind of put up a mask that looks at these two sides of life, of being happy and sad especially when they have to be hyper-masculine to survive,” said Sandoval, who curated an exhibit on lowriders that is now open at the Petersen Automotive Museum.
Negrete, who became a pioneer for popularizing black-ink prison-style tattoos, is now 67 years old and the owner of Hollywood Vatican Studios, a tattoo shop on the Sunset Strip. He has tattooed Danny Trejo, Josh Brolin, Billy Bob Thornton and other celebrities and over the years has done thousands of “Smile Now, Cry Later” tattoos, he said.
About a decade ago, Negrete brought new life to the duality of “Smile Now, Cry Later” when he tattooed the words on the back of Luis Rodriguez, the writer and 2014 Los Angeles poet laureate.
“It’s funny how old enemies can now become friends and partners in the arts,” said Rodriguez, who grew close to the tattoo artist because of their shared lived experience.
Rodriguez, like Negrete, grew up in L.A.’s gang culture during the early 1970s. At 15, he joined the South San Gabriel barrio gang, the Lomas. After being kicked out of his parents’ home, he experienced homelessness on the streets of L.A. He found solace in the Central Library downtown, where his passion for writing blossomed, an experience that laid the groundwork for his 1993 memoir, “Always Running: La Vida Loca, Gang Days in L.A.”
For Rodriguez, the masks and clowns resonate because they are “part of this idea that clowns are outside the margins,” he said. “They laugh when others are crying, and they reveal what we may not want to share.”
Growing up in San Pedro, L.A.-based artist Mister Cartoon, whose real name is Mark Machado, remembers seeing tattooed clowns on the arms of older men. Some of his friends also collected drawings of clowns on jailhouse envelopes sent by their dads.
“They weren’t circus clowns, they were different. They seemed to always have a sad face or were laughing. It was a trip, and it really caught my eye,” Cartoon said.
As a young man, he started to graffiti the image on walls across the city using black spray paint that he took from his father’s garage or stole from the hardware store.
In 2020, when he was searching for a quick Halloween costume, he sketched the clown face that would become one of his signature designs.
The image became so popular that Cartoon began selling clown masks for teams across the country — the Oakland Athletics, the Chicago Cubs and even the New York Yankees. It sold in online stores and is now being resold on sites such as EBay for up to $200.
When the Dodgers won the World Series last year, the mask was prominently featured during the championship parade.
“The win could have also gone the other way around because we had made Yankee masks too for all of our East Coast friends. Even though they were on the other side, they were still rocking their clown masks,” he said.
Cartoon says he feels protective of the image, which was created by and intended for L.A. Chicanos. At the same time, he recognizes an opportunity to share.
“It’s cool to see people embrace the cholo clown,” he said. “From Instagram and TikTok, they’re all just putting their expression on it.”
For Hernandez, the makeup artist, her chola clown face is a living, breathing art form that is both personal and something she wants to share with others.
As a kid, she said, she found herself drawn to the image as she saw it on the bodies of people around her.
“They were people that look like me now and they were all tatted and it started to resonate with me,” she said. “It was everywhere.”
As her social media following grows and she takes on new modeling campaigns, she sees it all as a celebration of L.A. lifestyle.
“People are more open to stuff now. But I also feel like people need to stay authentic,” she said. “Don’t just follow a trend, because this is not a trend, you know? This is something that’s been around.”
Frank Rojas is a freelance writer based in Los Angeles.
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