Hi all,
I want to introduce you to Kelly Boesch. She’s 62, she lives in Palm Desert, and until two weeks ago she was working a day job as a graphic designer while quietly becoming one of the most followed AI artists in the world.
I am not making that up.
She has millions of fans. They write to her every day. Thousands of people were spending real money on her music on Bandcamp. Then one morning she woke up and her entire catalog was erased. The site had banned her with no warning, communication, or way to reach the people who had been supporting her.
We are at a genuinely unresolved moment in the AI and art conversation, where the arguments are loud and polarized but the actual lived experience of artists using these tools is almost never centered. The debate is happening over people’s heads, not with them.
Kelly is a specific kind of entry point into that debate: someone who is not a tech person, or an activist, or a thought leader with a position to defend. She’s an artist who found a tool that unlocked something in her and has been living with all the complex consequences of that: creative, ethical, commercial, social. Out in the open, ever since.
She’s undeniable as an artist. She’s undeniable as a human. That doesn’t mean the conversation is simple.
Here’s some of what we get into:
What it actually feels like to make something with these tools, and what she’d say to a traditional artist who’s afraid to try
The role of taste: anyone can prompt something, but making something good requires a point of view, life experience, and vision she’s spent decades building (as we discussed with James Andrews back in 2024)
The surprising number of traditional musicians and artists Kelly knows who are quietly using these tools and not telling anyone
The audience that found her: people between 50 and 90 who engage with her work daily
What her manager and partner is building next: a curated platform where AI artists can actually sell their music, built for people who bring a real point of view
One more thing: this conversation goes to some genuinely complicated places around AI, representation, and artistic responsibility. Kelly, who is a white woman, made a beautiful viral video featuring Black dancers and didn’t think about what she was doing until people told her. And she’s very openly reckoning with a question that the tools themselves don’t ask and that none of us have fully answered: whose culture is available to whose imagination, and what do we owe each other when we reach for it? I’ll be honest: the video made me feel weird and it’s also genuinely dope. That’s the place this conversation lives.
That’s what we try to do at Life With Machines: hold the structural critique and the personal practice in the same room without dismissing or flattening either one.
Watch it. Then tell me in the comments: Have you dabbled in AI art yourself? How did it feel?
- Baratunde
Thanks to the entire Life With Machines team, especially Layne Deyling Cherland and Alie Kilts for editorial and production support.
