Tamara has been a judge since 2023

Tamara Jenkins with husband, Jay Montgomery, were co-Founders of Staten Island's first professional theatre company.

Tamara Jenkins

Bitter Jester Music Festival Judge

Tamara Jenkins spent the last 30 years as a professional actress in New York City before moving to the Chicagoland area. She is a classically trained singer and voice teacher with a Bachelor of Music from The University of Illinois (Magna Cum Laude). She currently serves as the Director of Focus on the Arts at Highland Park High School, the same program that BJMF Founder/Producer Nicolas DeGrazia credits with being a main driving inspiration and a big reason why BJMF exists!

Her BROADWAY / TOUR credits include: ‘Velma’ in Chicago, ‘Cosette’ in Les Miserables, ‘Demeter’ in Cats, the ‘Eliza’ cover in the Richard Chamberlain revival of My Fair Lady, and ‘Elyse Schulman’ in The New World. OFF-BROADWAY she appeared in Brel Returns at The Zipper Theater.

Her numerous REGIONAL theatre credits include: ‘Fiona’ in Brigadoon with Dick Van Patton, ‘Hodel’ in Fiddler on the Roof with Theo Bikel, ‘Guinevere’ in Camelot with Noel Harrison, ‘Glinda’ in Wizard of Oz with Bob Keeshan, ‘Christine’ in Phantom, ‘Anna” in The King and I, ‘Sarah Brown’ in Guys and Dolls, and many others.

TV credits include: Conviction, Another World, and Guiding Light.

Tamara has appeared as Featured Vocalist with jazz greats Wayne Shorter, Buster Williams, Larry Coryell, and Nestor Torres. She has also sung with The Richmond County Orchestra, The Lake Forest Symphony, the President’s Band, and at Carnegie Hall.

Additionally, she has had the honor of performing for President and Mrs. Reagan and President and Mrs. Clinton on multiple occasions! As a librettist, Tamara’s first script was a finalist for the prestigious Richard Rodgers Award. She produced and directed a reading of her show Steps in Time at The Henry Miller Theater, starring Milo O’Shea and Helen Gallagher, and helped produce a concert at Carnegie Hall celebrating 50 Years of UNICEF, starring Herbie Hancock and Art Garfunkel.

Tamara Co-Founded and served as Artistic Director at The Harbor Lights Theater Company in NYC. In her eight-year tenure there, the professional company presented 29 productions featuring over 100 Broadway actors, including Tony, Emmy, Obie, and Oscar winners and nominees. She made her Harbor Lights directing debut in the acclaimed 2011 production of Amahl and the Night Visitors.

Tamara is proud to have been awarded three times for her activities for Peace Through Culture from U.N.-affiliated organizations and is recipient of multiple ‘Awards of Merit’ from both New York State and New York City, as well as the ‘The Unsung Hero Award’ from the Non-Profit Association of Staten Island, and ‘Woman of Distinction’ from The New York State Women.

She is thrilled to be participating as a judge for the Bitter Jester Music Festival’s lineup of talented musicians, singers, and performers.