Houston rapper Le$ molds style, social-media savvy for a new generation
In April 2009, Lester Matthews scanned his office on the first day of a well-paying job at the U.S. Social Security Administration in Dallas.
Then he quietly walked out and never returned.
“Nobody looked happy to be there,” says Matthews, who in that moment said goodbye to an $80,000 annual paycheck without an explanation for his bosses.
He packed his bags, filled the gas tank of his Buick and headed back home to Houston, upset and uncertain about his future.
He didn’t know how he was going to make money. He just wanted to pursue rap.
“They say if you want to do something, you’ve got to be all in,” says Matthews, now 33. “So that was kind of like my ‘I’m going to be all in’ moment. And it was rewarded.”
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Matthews spent the next decade amassing a dedicated following under the hip-hop moniker Le$. He writes at a ferocious pace, releasing around 30 mixtapes since 2009 in a sub-genre he only describes as “lifestyle rap.” His fourth mixtape this year, “Gran Turismo 2,” will be released Sunday on all major streaming sites, including Apple Music and Spotify.
From the outset, Matthews’ style was unmistakable. His music evokes the feeling of slowly riding down the highway in a convertible with the top down. It retains the mellow feel of Houston’s signature chopped-up style in the 1990s, but with more melody. The distinct rasp in his voice cuts through the warmth of each song. Former Houston rap critic Shea Serrano compared the music to watching a sunset, because “it’s really pretty and all you can look at for a few minutes.”
He has been featured on multiple lists of the best rappers to follow in Houston, and he’s collaborated with big names like Slim Thug, Bun B and Mac Miller. But Matthews represents the next generation of Houston hip-hop — one that came up in the age of streaming and social media.
His peers attribute his success to studying the blueprint of social-media marketing. He has collected more than 30,000 followers on Twitter and more than 90,000 on Instagram. He reaches beyond Texas with around 3,500 monthly Spotify listeners in Los Angeles and 2,800 in Chicago. And Matthews, who owns a townhome in The Woodlands, further separates himself as an artist with his creative pace and consistency, says Houston rap promoter and MC Kane Brock.
“Le$ has already established a reputation for putting out a bunch of content, and his fans are just soaking that up,” says Brock, adding, “I don’t think I’ve seen Le$ deviate away from (his style). A lot of artists tend to paint different pictures sometimes, but Le$ knows exactly who he his.”
Early goals
Matthews was born in New Orleans but spent most of his time in Texas as a kid, attending both middle and elementary school in Tyler. He regularly visited family in Houston but didn’t settle down in the city until 2003, when he enrolled in classes at the University of Houston.
By then, everyone he met wanted to rap. Lil’ Wayne started gaining popularity and inspiring younger audiences. For Matthews, that meant recording freestyles on a Gateway laptop with his friends in a dorm room, resembling Houston rap icon DJ Screw’s recording sessions in the 1990s.
Matthews said he wasn’t yet interested in becoming a rapper. Before the dawn of social media and streaming platforms like Soundcloud, that was like “being a short dude who wanted to play basketball,” he says.
He wanted an apartment, a $15-an-hour job and spinners for his car. He worked various odd jobs through college — Blockbuster, Sam’s Club, Comcast — with much more practical ideas.
“Going back and thinking about it, I was setting myself up to have a dumb-ass life,” he said, “I didn’t have a goal, really.”
Matthews dropped out of school after three years. He was working at Comcast when he first learned about MySpace. The social-media platform opened a world where he could track his favorite rappers’ growth. He and other fledgling artists paid attention to how people marketed themselves by sharing more about their personal lives.
It felt authentic and diluted the promotional role of traditional record labels, says Houston rapper Chris Dudley, who goes by Propain.
“Nowadays, we are the label,” says Dudley, who came up in Houston’s rap scene around the same time as Le$. “That’s the big difference with the generation before us … a lot of my fans relate to me, to everything about me, because I give them my life and the things I go through.”
Around 2008, Matthews started recording his own songs in his bedroom. He burned them onto CDs and handed them out for free around Houston. He got positive feedback but couldn’t monetize the work. That’s when he took the job in Dallas.
At the time, he didn’t know that his demos had made the rounds.
The day after Matthews drove from Dallas to Houston, he ran into the DJ Mr. Rogers at a record store in Montrose. The DJ, who works as a record producer and sound engineer, liked his music and sent him beats to rap over. Matthews sent him back five finished songs overnight in what would become his first official project, “Settle 4 Le$.”
Subsequently, he got his first sweet taste of internet fame when approximately 2,800 people downloaded the tape the day of the release, he said.
“That’s when the light went off in my head,” Matthews says. “That was the first sign of me becoming who I am now. Like ‘Wait, I can make music that quick, just put it out and get like a response that fast?’”
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Matching style
Matthews released another project that year, “The Beautiful Struggle,” and gained momentum on underground hip-hop blogs. Fed by a growing social-media following, he started connecting with other rappers like Big K.R.I.T and Curren$y.
He never officially joined a major label, but he toured with such well-known rap collectives as Slim Thug’s Boss Hogg Outlawz and Curren$y’s Jet Life. He also built a clothing brand, Steak X Shrimp, with his partner, Jorge Casanova (aka Jorgey).
Matthews takes pride in his laid-back nature, both personally and musically. He doesn’t wear much jewelry. He burns through joints while talking freely about his early financial struggles. And his open enthusiasm for Pappadeaux Seafood Kitchen and Whataburger makes him relatable to a Texas fan base.
His themes are straightforward and sometimes playful. In one of his mixtapes, “The Catalina Wine Mixer,” the song titles pay homage to the movie “Step Brothers.” His song “In the Whataburger Drive Thru” ends with a recording of him literally placing an order in a Whataburger drive-thru. He often relates to his love for cars, which tie together the imagery in his lyrics and on his mixtape covers.
“I think one of the smart things that Le$ does is all of his stuff fits — it all matches,” says Shea Serrano, the author, contributor to the Ringer and a former hip-hop critic at the Houston Press. “The pictures that he puts out feel sunburnt. That’s always the word I’ve sort of fallen back to with him. It feels like the time of day when the sun is just on the horizon and the sky is like 45 different colors of oranges and purples and yellows. And that’s what his music feels like to me, too.”
Serrano met Matthews in 2009 when he was hunting for new talent to write about. He picked up one of Matthews’ tapes at a freestyle competition, and he’s been singing the rapper’s praises ever since.
“He’s one of the guys who figured out early on how to use the internet as a musician,” Serrano says. “He’s really good about interacting with fans, but also about giving everybody what they want.”
Matthews said he mostly supports himself with money from Spotify, which pays artists a fraction of a cent per stream. He boasts nearly 4,000 monthly listeners in Houston and Dallas alone. Online sales from his clothing brand also brings in money.
He books about around 20 shows a year, but he no longer feels obligated to take every opportunity play for an audience, he said. His healthy stock of online content keeps his name circulating, he said, and he’s not slowing down.
“Now, when you’re coming up (in music), there’s a lane for everything,” Matthews says. “If you be yourself, there’s going to be people who can connect with whatever you’re into.”
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