Interview: Sidney Jacobs: SIDNEY JACOBS & THE GREAT AMERICAN JAZZBOOK: Sierra Madre Playhouse @ 100

The African-American identified jazz singer, songwriter, arranger and producer SIDNEY JACOBS was completely unkown until he was asked to join as the newest member of the legendary psychedelic pop  group The Fifth Dimension. Born in LA, Jacobs composes great songs with elements of bop, R&B, swing, soul, sound experiments and the Great American Songbook. His 2017 debut album, ‘First Man’, was critically acclaimed on all major sound paltforms. The concept for this new album came about through one of his live performances but you will hear his cool sounds on a hot August night at The Sierra Madre Playhouse @ 100 Summer Jazz Series. (tix click:  sierramadreplayhouse.org)

Broadway World New York suggested Broadway World Los Angeles' (this columnist)  to invite Sidney Jacobs to answer my noted TEN QUESTIONS IN TEN MINUTES to pull back the cutain on his rise to jazz fame: 

What constellation were you born under in what month of the year?

My birth month is August, and my sign is Leo.

Can you remember the first live performance you ever attended?
Yes, the first real concert I attended was Earth Wind and Fire at the Forum. That concert blew my mind and set the course of my life-long ambitions.

Your name is quite prominent within the Jewish community; how did you come by it? Do you find that it surprises people when you arrive on the scene?

LOL!… Well, I think we can guess how I came by my sur name. Slavery has a long legacy in the US. I don’t find people are surprised when I show up, however when I was a young professional musician, I performed as a cantor (subbing for a friend of mine), and, yes, when I showed up at the synagogue, they were indeed surprised. (Fun Fact: Larry David while on PBS FINDING YOUR ROOTS was abhored to discover he was a descendant of Lousiana slave owners who identified as Jewish, he later did a tik tok video of his ancestor sitting with Rosa Parks on her bus but this time intervening on her behalf and telling the biggots to go sit in the back of the bus to atone for his relatives)

Where did you develop your ear for jazz? 

My brother introduced me to jazz when I was an adolescent. I’ve always had an advanced ear, but he taught me how to listen to the music, and his lessons have stayed with me my entire life. 

Regarding the distinction between jazz and Black American Music (BAM), where do you see yourself fitting in among the giants (Nina Simone and Nat King Cole) of the genre?

I stand in awe of all the major and minor musicians who have come before me. I can’t presume to even be able to stand on the same stage as them. I hope that they would recognize that I love and respect the music and that I’m not afraid to explore as a vocalist, and that I bring honor to the tradition. 

A. What is the personal draw for you when performing with a live band?

Performing with world class musicians is an awesome privilege and a singular experience that I do not take for granted.  To sing in front of world class players is both challenging and comforting. I love to drive a band when I sing, and, in order to do that, one must feel supported and protected. It’s an awesome experience. 

B.  How difficult is it to be an original artist playing original music today?

It is very challenging to go one’s own way artistically. The temptation is to conform to an existing sound, because people love to hear music that they already know. For the original artist, that means you have to hustle to get the music in front of as many ears as possible and hope folks gravitate toward it. 

 C. Sierra Madre (mother of all mountains) is celebrating 100 amazing years  but do you believe jazz will still be a prominent art form in the next 100 years?

Jazz is a home-grown art form created in America through the musical connection with the African diaspora and forged in the heat of blues, gospel and the musical foundation of European classical music.. YES, jazz in various forms is here to stay. 

As a former School Psychologist, is it difficult to walk away from that dynamic given the need for positive male role models in education?

Good question. I was a practicing school psych for over 20 years. And prior to that, I taught kindergarten.  In that role,I was able to positivity impact the lives of hundreds of families. That is a very rewarding experience. But, throughout that time, I knew that my outsized talent was that of a singer and songwriter. So, it was not hard to walk away. Said another way, it was imperative that I walk toward my dream of being a working musician. 

Have you performed in the famed Paris jazz scene?

NO. I have performed in Paris as a professional singer, but not in jazz.  I am aching to perform in Europe. 

What is your endgame—a TED talk, a Netflix special, or perhaps a collaboration with an artist like Herbie Hancock?

I don’t live my life that way anymore. My goals now are to show up where I’m invited and do my absolute best in that space. I’m letting the music take its course…thinking that way takes the pressure of expectation off of me. 

Outside of the Sierra Madre Playhouse, what other Los Angeles venues provide the warmest embrace from your audiences? 

I would say that Birds of A Feather Jazz Lounge provides an exceptional environment for serious musicians. My business partner and I run the club and the overwhelming comments from our artists and patrons is that it is a beautiful and supportive place. We are very proud of that. 

The historic Sierra Madre Playhouse and SIDNEY JACOBS have both  earned a reputation as one of the Southland’s leading jazz presenters in recent years, continues their popular Jazz @ the Playhouse series with noted jazz and R&B vocalist and songwriter Sidney Jacobs on Sunday, August 2, 2026, 8:00 PM. Jacobs, hailed for his smooth velvety tone, inventive phrasing, and heartfeltdelivery, leads a dynamic quartet through a set that blends original music with reimagined standards filtered through a contemporary groove.

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