🎨 Kyle Lucks: Painting Icons, The Pressure of Perfection, and Why He Hasn’t Painted Taylor Swift (Yet)
Celebrity artist, Kyle Lucks, opens up about how he got started as an artist, his creative process when painting some of the world’s most recognizable faces, how to commission a custom painting from him, and why he has an affinity for painting professional athletes.
He’s painted Serena, Jack, Coco, and Rick Ross. His work hangs in sports arenas and Palm Beach estates. And this year? Kyle Lucks became the artist everyone’s watching.
In this episode of In The Hype Seat, host Holly Meyer Lucas sits down with celebrity portrait artist Kyle Lucks for a hilarious, candid, and behind-the-scenes look at what it really takes to paint cultural icons everyone knows—and get it exactly right. From commissioned portraits of Abraham Lincoln and Donald Trump to a Billie Jean King trophy reflection moment that broke the internet, Kyle opens up about the high-stakes pressure of his craft and why he only paints stories that give him goosebumps.
From Studio to Stadiums
Kyle Lucks is known for his expressive brushwork, layered textures, and spot varnish storytelling that you have to see in person to believe. But what most people don’t see is the creative process behind the canvas. In this episode, Kyle breaks down how each painting begins with a vibe, a vision, and a wild amount of Photoshopping, sketching, and custom composition work before the first drop of paint even hits the canvas.
We hear how his portrait of Serena Williams became a full-circle moment, how Jack Nicklaus signed his finished piece before it was auctioned off, and how a subtle nod to Billie Jean King’s legacy ended up going viral for its clever placement of her reflection in the trophy.
Kyle also shares how he builds emotional connection into every piece—whether he’s honoring sports legends, painting Rick Ross with thoughtful symbolism (that Holly still feels some type of way about), or planning a future Michael Jordan piece inspired by a Jay-Z lyric about Game 6.
The "It" Artist of the Season
Over the past year, Kyle has become a fixture in the Palm Beach art scene. Between his Artist in Residence spotlight at the Historical Society of Palm Beach County, a headline-making collaboration with the U.S. Polo Association, and a flood of high-end commissions, Kyle’s brand has gone next level—without losing an ounce of creative integrity.
In the episode, Holly and Kyle talk about what it’s been like working together behind the scenes at Hype Boss. From building Kyle’s social presence and e-commerce print business to navigating press and brand visibility as his career explodes, they keep it honest and funny. Holly dishes about her campaign to get Taylor Swift on one of Kyle’s canvases, while Kyle holds firm on only painting subjects that move him emotionally.
Episode Highlights
The real process behind Kyle's most iconic portraits (Photoshop layers, grid transfers, and last-minute changes included)
The pressure of painting faces everyone recognizes—and what happens when you don’t nail it
The now-infamous Jimmy Buffett lyric mistake (and how a new brushstroke saved it)
Why the Rick Ross painting keeps going viral—and how it drives Holly nuts
The Game 6 Michael Jordan concept inspired by a Jay-Z lyric
The artist’s code: Why Kyle hasn’t painted Taylor Swift (yet)
Why You Should Listen
This episode is a front-row seat to what it's like being a full-time artist in 2025. Kyle doesn’t just paint famous people—he captures the emotion, energy, and legacy that define them. Whether you're an art lover, brand builder, or creative entrepreneur, this conversation is packed with takeaways on vision, pressure, staying true to your taste, and building a brand with emotional depth.
🎧 Listen to the full episode: In The Hype Seat: Kyle Lucks
🎨 Explore Kyle’s work or commission a portrait: kylelucks.com
📍 Recorded at PodPlus Studios, Jupiter, Florida
🎙 Produced by Hype Boss | hypeboss.com
