A Conversation with Jonathan Estabrooks


Jonathan Estabrooks

With a remarkable voice and superb stage presence, Jonathan Estabrooks remains one of his generation’s premiere baritones. (Photo courtesy of Jonathan Estabrooks)

By: Jacob Elyachar, jakes-take.com

One voice that you need to keep an ear out for is Jonathan Estabrooks.

The Ottawa, Canada singer trained in opera and mastered multiple musical genres including classical and popular music. He also performed in front of former President Bill Clinton, the Prime Minister of Canada and members of the United Nations.

Jonathan also had the opportunity to perform in iconic venues such as the Lincoln Center and Carnegie Hall. He also performed alongside Broadway superstars Ashley Brown and Aaron Lazar.

Recently, Jonathan released his debut album, These Miles, which showcases his take on classic arias and pop classics.

In this edition of A Conversation, Jonathan talked about the biggest misconceptions Millennials have towards opera, These Miles’s recording process and his thoughts about auditioning for Got Talent and The Voice.

Jacob Elyachar: When did you get interested in opera?

Jonathan Estabrooks: I have been pretty much doing it all my life.

I started singing at a very young age. I started doing voice lessons and was part of a Boys’ Choir in Ottawa and I did a lot of productions with them. They were associated with the local opera company and I started studying with the choir director.

JE: What are some of the biggest misconceptions that our generation (the Millennials) has about opera?

JEstaB: One of the biggest misconceptions that Millennials have about opera is that it is stuffy and that they can’t relate. They also think that opera is only for the rich and cultured. Opera was the people’s musical theatre of its time. Unfortunately, as time went on, it became a museum that reflected a bygone era of music. Thankfully, we have been seeing a lot of new material in the past five years, which has been…interesting to say the least. New productions have been connecting elements of musical theatre with opera and working hard to make the art form current and relatable.

I think people need to realize that opera is about story. It has the same basic emotions like love, hate, sadness and joy that any piece of music expresses. The stories are dressed differently, but the basic tenants of the stories are basic human emotions and transcended generations. If they give opera a chance, they will realize that it is a pretty fantastic thing!

JE: What were some of your favorite roles that you played? Why did those characters stand out to you?

JEstaB: I enjoyed playing Papageno from The Magic Flute. He represented humanity’s imperfections and had a child-like innocence about him. I also enjoyed wearing his outlandish birdman costumes and running around the stage. One character that I hope to play is The Barber of Seville’s Figaro. He sings the well-known ‘Largo al Factotum’.

JE: Let’s talk about your debut album: “These Miles.” Why did you want to record it?

JEstaB: I had harbored the dream for many years to do something. I always wanted to find a way to bring my various musical loves together into one creative project. I had gotten projects to a certain point and for whatever reason they fell through. I think I was subconsciously putting obstacles in my way. I finally decided to give it another go and turned to Kickstarter to reach my fanbase and fund the project. It snowballed from this hobby project into this huge, orchestral debut album. I picked songs that I loved from the classical and pop worlds and worked with my amazing friend and collaborator, Oran Eldor who created these incredible orchestrations. More than anything, I wanted to bridge generations by connecting styles of music. I grabbed the classic arias, the Big Band and Neil Diamond songs and shook them up! Some really magical things started to happen…. thanks in part to some incredible friends and people that got behind the project.

Jonathan Estabrooks These Miles album

Jonathan Estabrooks’s “These Miles” features his takes on classic arias, Big band anthems and 80s tunes. (Album cover property of Jonathan Estabrooks)

JE: What were some of the challenges that you faced while recording the album? How did you overcome them?

JEstaB: There were many, many challenges along the way. “How was I going to raise all the money on Kickstarter?”, “How would I, technically coordinate with an orchestra based in Macedonia?” There were times that I wanted to hit my head against the wall. I pushed through it and learned to always expect the unexpected and about the reality of the record making business…that is a really big and unpredictable animal.

JE: One of my favorite arias on your album is “Por Una Cabeza” with Jonathan Antoine. How did this collaboration come about?

JEstaB: I will give credit where credit is due and the collaboration came from a super fan. I received a message on my Facebook page and they told me that I had to meet this young tenor named Jonathan; he was interested in learning more about Opera. At the time, I did not know who he was. A couple of days later, I received a message from Jonathan Antoine himself and learned that he had 100 million views on YouTube and had been a runner-up on Britain’s Got Talent.

By the time Jonathan reached out, I had already been looking to learn more about the classical crossover genre. At the same time, he was looking to learn about my experience at Juilliard. We began this online pen pal relationship. As time went by, I told him about my album and asked him if he wanted to do a duet. He agreed, his management got on board and though it took some work with the label, Sony agreed. Jonathan recorded his part in England and sent it to me. It was such a joy and I think you can really hear that in the duet!

JE: I loved your cover of Cyndi Lauper’s “Time After Time.” Did you ever have the chance to present the song in front of her?

JEstaB: I have not had the pleasure of presenting it to her personally. I tweeted a link to her and Dave Reitzas, my producer in LA, worked with her numerous times. My hope is that it can get in front of her at some point. I would love to know what she thinks. We definitely took a different take on the classic tune by striped it down to its basics and bringing in the orchestral element.

JE: A lot of classical crossover artists including Jonathan, Andrew De Leon, the Forte Tenors, Branden James and Chris Mann have successfully reached broader audiences on “Got Talent” & “The Voice.” Have you thought about auditioning for those shows? Why or Why not?

JEstaB: I have had long conversations with confidants about auditioning for those shows. I have never been 100-percent against it or 100-percent for it. The thing that has scared me is my understanding of the artists’ contractual obligations. They can be daunting. I think one needs to really know what they are getting into. I am not against those types of shows but just be informed. If the opportunity presents itself in a way that could help me reach a broader audience…I would certainly be open to it.

There are those success stories, but there are also stories about people who explode to stardom and then, they are eliminated during the third or fourth round of the competition. They just went through an emotional roller coaster and nobody knows where they are and who they were before the show, this left them worse off than they were before. If anyone is going to go through that route, they need to fully understand what they are signing and be prepared that this could go somewhere or nowhere and be prepared for both options.

JE: If you had the chance to meet with an aspiring performer who wants to enter the entertainment industry, what advice would you share?

JEstaB: Both the performing and recording sides of the industry interchange with each other. I have worked on the performing side for a very long time and I am just starting to learn about the record industry…. which is a lot different. My first piece of advice is really do your homework! Be somebody who is easy and very fun to work with. Have a vision and really be able to stand up for your vision. Make sure that you show the audience that you are having fun…it will be easier for them to connect with you.

As for the record industry, it is 10-percent music and 90-percent business. Not to scare anybody off, but you realize very quickly that artists who have millions of plays on Pandora, Spotify and YouTube…are making pennies on the dollar. The business has been transformed in both good and bad ways, if you want to go into this business; it is imperative that you know what you are getting into. Read all the fine print and look it over with a lawyer before you ever sign something. Also, just be aware! I know a lot of young people have stars in their eyes, but know that you have to protect yourself and make sure that they have your best interests at heart.

To learn more about Jonathan Estabrooks and his new album, visit his website: http://jonathanestabrooks.com/

You can also connect with Jonathan on social media! Visit his Facebook, Twitter & YouTube channels!





  1. It’s nearly impossible to find experienced people for
    this topic, but you seem like you know what you’re talking about!

  2. Thank you ever so for you post.Much thanks again. Really Great.

Copyright 2020 Jacob Elyachar