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Jacob Jeffries on grief and groove

Jacob Jeffries is the latest guest on The Third Story podcast with host Leo Sidran
The Third Story/Leo Sidran
Jacob Jeffries is the latest guest on The Third Story podcast with host Leo Sidran

Pianist, songwriter, and performer Jacob Jeffries has been making records since he was a teenager in south Florida. He signed a publishing deal at 18, and made a flurry of early recordings. But only now, after two decades of persistence, loss, and reinvention, does it feel like his moment is arriving.

Jeffries grew up in a Beatles household. He was that kid who wore a Fab Four t-shirt to school every day. Summers were spent at Lovewell, a theater program where students and staff created original musicals together. It was an early education in the power of collaboration that would later serve him well. As a young artist, he was taken under the wing of Grammy-winning producer Sebastian Krys and guitarist Dan Warner, who shepherded him into the studio and helped him navigate his first deals. On paper, it looked like a fast track to stardom.

But life intervened. Jeffries lost his father suddenly when he was 19, and then his mother to cancer just a few years later. Those twin tragedies left him and his sister to find their own paths - hers through the stability of family and nursing, his through the itinerant world of music. Grief became a shadow and a motivator, something to process and honor through songs.

Jacob Jeffies and Leo Sidran
Leo Sidran
Jacob Jeffies and Leo Sidran

What makes Jeffries unusual is how he channels that history. On stage with Vulfpeck, he is pure energy and absurdist humor—dancing, singing, mugging for the crowd, a surrealist performance artist in the middle of one of the most musically adept and conceptually playful bands of the era. When Vulf played Madison Square Garden, Jeffries was as likely to be found “miping around” - that’s what he calls it - in a bit of on-stage shtick as he was delivering a soaring vocal. He embodies the band’s ethos: no single star, everyone shines, everyone plays.

And yet his own music reveals another side entirely. His new record, You Got the Right Idea, produced by fellow Vulfpeck bandmate Theo Katzman for Katzman’s 10 Good Songs label, is quiet where Vulfpeck is raucous, vulnerable where the stage show is winking. The songs are intimate, sometimes whispered, full of reflection on love, loss, family, and the slow accrual of wisdom. One song confronts a child moving “one seat down” toward independence; another imagines his grandparents’ love affair in Poland in the early 20th century, and yet another takes a more playful, Beatles-esque detour, reminding listeners not to take it all too seriously.

Jacob Jeffries
courtesy of the artist
Jacob Jeffries

Because in Jeffries’ world, sincerity and satire are not opposites but companions. The high-energy clowning and the hushed confessions both come from the same place: a need to live fully, to honor the weight of experience without being crushed by it.

So ultimately “emerging artist” isn’t a contradiction after all. Jacob Jeffries has been at it long enough to know what it means to endure, to reinvent, to keep creating. If it feels like he’s just getting started, maybe that means he’s doing it right.

We spoke recently about grief, his bond with Theo Katzman, the power of collaborative creativity, and the balance between sincerity, playfulness in his own music, and how he embodies a kind of singer, storyteller, and surrealist performer all at once.

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Leo Sidran is a Grammy winning multi-instrumentalist musician, producer, arranger, composer, recording artist and podcast host based in Brooklyn, New York.