People usually think they know everything about a celebrity's life from a documentary. Then things change.
If you followed the saga of Jason Isbell and Amanda Shires, you probably saw the HBO film Running with Our Eyes Closed. It was raw. It was uncomfortable. It showed a marriage held together by music, sobriety, and sheer will. But by December 2023, that thread finally snapped. Isbell filed for divorce, and the "Johnny and June" of the Americana world were officially over.
Now, there is a new name in the mix. Anna Weyant.
She isn't a fiddle player from Texas. She’s a 30-year-old superstar in the high-stakes New York City art world. Honestly, the pairing feels like a movie script: the gritty Southern songwriter and the refined Canadian painter who sells canvases for millions. But if you look closer, the connection between Jason Isbell and Anna Weyant makes a weird kind of sense. They are both "muses" for one another in a way that has fundamentally shifted Isbell's creative output.
Who Exactly is Anna Weyant?
She is not just some "new girlfriend." In the art world, Anna Weyant is a phenomenon.
Born in Calgary, she moved to New York and became the youngest artist ever represented by the Gagosian gallery—the gold standard of the art industry. Her paintings are dark, figurative, and often a little bit surreal. They’ve sold at Sotheby’s for over $1.6 million. Basically, she’s a big deal on her own.
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The two met in early 2024. According to reports from the Wall Street Journal, Isbell actually reached out to her after reading a profile of her in GQ. He liked her work. She liked his music. By February 2024, they were a couple.
It was fast. Some fans were, frankly, a little shocked. They were used to seeing Jason and Amanda as a unit. But life moves on, and for Isbell, it moved toward a studio in New York.
Foxes in the Snow: The New Muse
You can hear the change in the music. On March 7, 2025, Isbell released a solo acoustic album titled Foxes in the Snow.
The cover art? It’s a painting by Anna Weyant.
It isn't just a business collaboration. The songs on the record feel different than the 400 Unit rock anthems. They are quieter. More intimate. In the track "Open and Close," Isbell basically confirms the relationship with lyrics about a woman who "reminds him of Calgary."
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The Divorce is Final
While the romance was blooming, the legalities were still grinding away in Tennessee. On March 4, 2025, the divorce between Jason Isbell and Amanda Shires was officially finalized.
It took over a year.
Isbell has been pretty open about why it ended. It wasn't about cheating or some big blowout fight. He told the WSJ that the atmosphere had become "unbreathable." He felt like he couldn't share his successes because the power dynamic in the marriage had become so skewed. It’s a sad, human reason for a split.
Why This Relationship Matters
Dating a painter of Weyant's stature has shifted Isbell’s social circle.
He’s no longer just the king of the Nashville Ryman residency. Lately, you’ll find him at the Tiffany & Co. Blue Book Gala or MoMA benefits in Manhattan. He’s leaning into the New York art scene. Is he a "gold digger" like some Reddit threads suggest? Probably not. The guy has plenty of his own money and a burgeoning acting career (remember Killers of the Flower Moon?).
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It seems more like an intellectual match. They are both creators at the top of their respective fields.
- The Age Gap: There is a 16-year difference (Isbell is 46, Weyant is 30).
- The Vibe: It's very "Art School meets Americana."
- The Legacy: He still plays the songs he wrote for Amanda. He says those songs don't belong to him anymore; they belong to the fans.
What Most People Get Wrong
The biggest misconception is that Anna Weyant "broke up" the marriage.
The timeline doesn't actually support that. Isbell filed in December 2023. He didn't even reach out to Weyant until February 2024. People love a villain, but this looks more like a man who was already finished with one chapter before he started the next.
Actionable Insights for Fans
If you're following this story, here is what you should actually do to understand the "new" Jason Isbell:
- Listen to Foxes in the Snow: It is his most stripped-back work in a decade. It’s the sound of a man finding a new center.
- Look at Weyant's Art: Check out her "Loose Tooth" or "Falling" series. Understanding her visual style gives you a huge hint into the aesthetic Isbell is currently drawn to.
- Respect the Boundaries: Both artists have been fairly private about their day-to-day life, despite the high-profile gala appearances.
The "Johnny and June" era is over. The "Jason and Anna" era is just beginning. It's colder, more precise, and maybe exactly what a 46-year-old songwriter needs to keep from repeating himself.
To see the influence for yourself, start by comparing the lyrics of "Cover Me Up" to "Open and Close." The shift from desperate survival to a sort of quiet, new-found peace is the real story here.