KCK milkman reclaims his passion for painting; splattering pop art portraits of KC sports stars, celebrity icons
April 16, 2024 | Nikki Overfelt Chifalu
While his pieces don’t feature happy, little trees, David Alston’s pop culture-inspired portraits still reflect the influence of the iconic painter Bob Ross.
About a decade ago, a chance viewing of the well-known artist’s PBS show “The Joy of Painting” — Alston’s youngest son accidentally left the TV on before leaving for school — inspired the Kansas City, Kansas, creator to pick up a paintbrush again.
“Just watching him, a bell went off and something spoke to me and said, ‘David, you can do this; you used to do this,’” he recalled. “And I realized, ‘Oh my god, I did. I used to do art.’”
After setting aside his passion for decades to focus on providing for his family, Alston has found a renewed sense of purpose in painting and sharing it with others. Although he still works full-time as a truck driver for Roberts Dairy, he spends his free time in his home studio and displays — and sells — his work across the city, including at Art Garden KC and restaurants and coffee shops like Blue Koi in Leawood, Tanner’s in Shawnee, BlendWell Community Cafe in Independence, and Summit Pizza in Lee’s Summit.
“There’s so much opportunity,” he added. “There’s so much art culture out here.”
Click here to view Alston’s art on Instagram.

A painting by David Alston featuring Kansas City Chiefs’ Travis Kelce, Patrick Mahomes and Andy Reid; photo by Nikki Overfelt Chifalu, Startland News
Growing up in Baltimore, Alston — who was inspired by his aunt — was always drawing, he explained, even selling his sketches of supercars to grade school classmates for a quarter. Upon graduating from high school, he received art scholarship opportunities to three different colleges. But despite his mom’s encouragement to follow his passion into higher education, he turned down those offers to join the U.S. Army. He wanted to financially support his mother, who worked several jobs to raise him and his brothers as a single mom.
“I didn’t really know what I was doing,” he continued, “but all I saw was the financial part of it.”
A couple times over the years, Alston noted, he flirted with his first love, doodling and sketching at his desk job on base in Fort Riley after getting injured. He used his cartoon illustrations as a motivational tool while working as restaurant manager in Kansas City after being discharged from the Army.
But it wasn’t until he happened upon that Bob Ross “therapeutic” tutorial that he fully recommitted to being an artist, beginning with working his way through the PBS painter’s videos.
“I started from there, doing landscapes and seascapes,” he explained. “Then I realized, ‘I think I’ve got this down. It’s time to learn something more.’”
Alston — who considers his style to swing between spontaneous realism, basic realism, and hyper realism — devoured tutorials from artists on YouTube and other social media platforms, he continued, ultimately focusing on portraits, which he considers to be the highest level of art.
“Not that everybody can do landscapes and seascapes,” he continued, “but they don’t present as much of a challenge as portraits.”

Paintings by David Alston feature the faces of The Three Stooges, Albert Einstein, and Elvis; photo by Nikki Overfelt Chifalu, Startland News
Whether splattered with bright colors or sketch-like in black and white, many of Alston’s portraits are inspired by photos of celebrities, especially Kansas City sports figures.
“Sports is the No. 1 thing that inspires me, especially when your teams are winning,” he said. “I couldn’t have found a better place to choose to live.”
Alston is constantly challenging himself, he noted, recently starting to do his paintings on epoxy and resin instead of the traditional canvas. His first experiment with the new materials featured Patrick Mahomes on a giant arrowhead.
“I said, ‘Oh my god, I love this thing,’” he recalled. “And usually, if I love something, I think a lot of other people are probably gonna like it, too. I started displaying it and it started getting more attention than my regular artwork.”
2024 Startups to Watch
stats here
Related Posts on Startland News
ECJC relocates office, updates brand
The Enterprise Center in Johnson County is shaking things up. The non-profit organization that connects entrepreneurs to the resources they need to grow revealed Thursday an updated website, brand identity, and new office location. “This move is the culmination of a long, strategic transition to ensure that as Kansas City’s entrepreneurial community changes, we change…
Former Sprint COO LeMay dishes on KC capital, failure
There are few people in Kansas City more connected into the area’s investor, corporate and startup community than FarmLink CEO Ron LeMay. Also now managing director of Kansas City-based OpenAir Equity Partners, LeMay frequently sees the successes and failures of the metro area’s capital landscape. The former Sprint COO recently spoke with dozens of Kansas…
RFP365 partners with Kansas City, raises $950K
On the heels of a six-figure raise, area tech firm RFP365 recently landed the City of Kansas City as a client for its software that eases the request for proposal process. The company’s deal with Kansas City was born from the city’s “Innovation Partnership” program, which affords entrepreneurs the opportunity to “test drive” their technologies…
Study: Gov should take long-term approach to grow new businesses
A recent study by the Ewing Marion Kauffman Foundation reports that while governments have long supported entrepreneurship, new business creation is waning. The study — Guidelines for Local and State Governments to Promote Entrepreneurship — found that new businesses comprised about 8 percent of all U.S. businesses in 2011, down from roughly 15 percent in the…





