Solo/Duo – Small Combinations
Ideal for cocktail / dinner parties or for small gatherings

testing to see if I can stretch the image to full width on mobile
Jay Middleton & Chris Pimentel are an acoustic duo who perform in the Bay Area & Wine Country. With a massive songbook of songs across all genres and eras, they always have a song for every party guest. Their duo is the perfect fit for any event, whether as background/listening music for a cocktail/dinner party or for a fun & funky small band dance party – or both. Chris provides the lead guitar and background vocals, while Jay provides the lead vocals backed by piano, guitar and ukulele.

Chris Pimentel is widely regarded as one of the premier guitarists in the San Francisco Bay Area. Since 1989, Chris has provided world-class solo jazz guitar for Napa Valley events at Opus One, Cuvasion Estate Wines, Clos Pegase, Mumm Napa Valley and many other prestigious winery venues. His noteworthy career has also included performances in top jazz combos, rock bands and theater orchestras.
A seasoned performer and Berklee College of Music graduate, Chris has shared the stage with some of the biggest names in pop history, including Michael Feinstein, Al Wilson, The Coasters, The Drifters, The Platters, and Tommy Tutone. His Broadway credits span acclaimed productions such as Jersey Boys, Mamma Mia, The Full Monty, Wicked, Hairspray, The Color Purple, Annie, Spamalot, Cats, Big River, and Disney’s High School Musical.
In addition to his work on Broadway and with major artists, he has been a vibrant part of the Bay Area music scene, performing with top party bands like the Dick Bright Orchestra, Encore, The Jay Middleton Party Band, Big City Review, City Lights, Full Motion, All Star Jukebox, Mustache Harbor, and Tainted Love. He currently serves on the music faculty at Santa Rosa Junior College.

Since 1985, Jay Middleton has performed over 3,000 shows across the U.S., lighting up festivals, parties, and venues with his powerful, expressive voice. Widely recognized as one of the Bay Area’s premier vocalists, he’s known for his ability to sing almost anything—effortlessly crossing genres and decades with ease. For 20 years, he led the popular party band All Star Jukebox before launching the Jay Middleton Party Band in 2023.
As a songwriter, he’s landed three tracks on the U.S. Top 40 charts, earning national airplay and sharing stages with major artists along the way. His 2024 album Forward marked a triumphant return to the charts, 27 years after his last hit. The record earned two first-round Grammy nominations and drew praise from the San Francisco Chronicle’s Joel Selvin, who called it “a seamless evocation of timeless musical values…soulful but sophisticated.”
A Stanford University film major, Jay lives in the Bay Area with his wife, two kids, a cat, and his beloved dog, Bucky.
Booking & Live Demo
Check out the Jay Middleton & Chris Pimentel live acoustic duo demo now!
Bookings:
Angela Takeshi — Wine Country Entertainment
(707) 598-8685 | angela@winecountryentertainment.com
FAQs
common questions / answers…