Kymberlee O'Brien
Overview
Kymberlee's EPK at ReverbNation: (link hidden)
Kymberlee is a 2025 Grammy-balloted singer-songwriter. Her sets include covers from Diana Krall, Norah Jones, Bill Withers, Stevie Wonder, Amy Winehouse, and soul and R&B favorites.
Kymberlee O'Brien is known for a smooth, versatile style with elements of jazz and soulful R&B; her voice is described as rich and expressive.
Kymberlee is a jazz vocalist who hails originally from California, where she performed in world-class jazz clubs along the Pacific Coast Highway, including La Jolla, Santa Barbara, and San Francisco. She now lives in Massachusetts and plays in local venues.
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Price range: $450 and up
Languages: English
Gig length: 60 - 180 minutes
What to expect
Expect a set that moves comfortably across jazz standards, soulful R&B, and pop — drawing on Ella Fitzgerald, Diana Krall, and Billie Holiday through more contemporary voices like Norah Jones and Amy Winehouse — delivered solo, voice and keyboard, with the intimacy of a one-woman show rather than a full band.
My style leans on smooth transitions between vocal registers, soulful R&B-inflected phrasing, and the technical control to navigate a complex melody without losing the emotional line underneath it. One reviewer described it this way: "Kymberlee O'Brien's timbre is a signature blend of warmth and clarity — each note shaped with refreshing nuances that breathe new life into jazz standards." Another put it more simply: "In a world of volume, she chooses depth."
I read the room and shape the set to it — a farmers market crowd gets warmth and momentum to keep people moving and lingering; a private event gets something closer to a listening-room experience, with space for the quieter, more intimate material. I'm a 2025 Grammy-ballot-recognized singer-songwriter (Best Pop Solo Performance, "Love Is Gonna Do Another Day," 67th Annual Grammy Awards), and that same level of care goes into a 40th birthday picnic as it would a stage.
About
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Kymberlee was recently conferred a Grammy 67th ballot for best pop solo original. Kymberlee has been a singer, songwriter, and dancer as long as she can remember. She is an award-winning songwriter and choreographer, known for her creativity and energy. Deeply involved in musical theatre as a child, she later studied with international percussion masters and this year became sponsored by Remo Percussion. Originally hailing from California, she played at several jazz and notable nightclubs in La Jolla, Santa Barbara, and San Diego, as well as festivals and private events.
Services offered
Upcoming booked events
August 2026
16
Sunday
Hopkinton Summer Concert Series
5:00pm - 7:00pm
25
Tuesday
Norwood Outdoor Market
2:00pm - 4:00pm
Past booked events
September 2025
20
Saturday
Walpole festival
10:00am - 1:00pm
13
Saturday
Natick festival
10:00am - 12:30pm
Set list
Set lists of artists include:
Examples:
Dianna Krall
Norah Jones
Ella Fitzgerald
Bill Withers
Amy Winehouse
Doris Day
Nancy SInatra
Michael Buble
Frank Sinatra
Bobby Derrin
Patti Smith
Bruce Springsteen
Bonnie Raitt
Ricki Lee Jones
The Motels
Nina Simone
Jazz standards
Influences and inspiration
Cl
My sound is built on a few different traditions that all feed into each other. In the jazz vocal tradition, I draw from Ella Fitzgerald, Diana Krall, Billie Holiday, Anita O'Day, Sarah Vaughan, Peggy Lee, and Louis Armstrong — the phrasing, the way a standard can be reshaped every time it's sung without losing what makes it a standard.
The blues runs underneath a lot of that: Muddy Waters, Big Mama Thornton, John Lee Hooker, and Sonny Boy Williamson taught a rawness and directness that jazz alone doesn't always ask for.
From soul and R&B, I take the warmth — Aretha Franklin, Al Green, Otis Redding, Sam Cooke, Bill Withers, Stevie Wonder, and Sade, all artists who could make a room feel like a conversation instead of a performance.
More contemporary and crossover influences round it out: Norah Jones, Amy Winehouse, Michael Bublé, Eva Cassidy, and Bonnie Raitt, each proof that these older traditions still have somewhere new to go.
And roots and singer-songwriter honesty come from John Prine and Mose Allison — plainspoken, unpretentious storytelling that keeps a lyric grounded no matter how much the arrangement moves around it.
Two more stand entirely on their own, because they're not really comparable to anyone: Nina Simone and John Coltrane. Not influences so much as reminders of what's possible when the music comes first.