Terrence Flannery: Surrounded By Brilliance

June 2, 2023

Terrence Flannery – Courtesy of The Center for the Performing Arts. Used with permission.

On April 29, I had the opportunity to witness one of Michael Feinstein’s finest concerts, “Get Happy: Michael Feinstein Celebrates the Judy Garland Centennial,” at the Palladium at the Center for the Performing Arts. Ever since the Center opened in 2011, I have had the pleasure of seeing Feinstein perform regularly at both the Palladium and at Feinstein’s at Hotel Carmichael, which opened two years ago directly west of the Center.

Having reviewed Feinstein’s shows at the Center since it opened, I have also covered the Songbook Academy summer intensive for the past 10 years of its existence.  During that time, I interviewed Feinstein numerous times as well.  Feinstein is the artistic director for the Center, and co-founded the Great American Songbook Foundation, headquartered at the Center, and conducts business related to both organizations in Carmel, where he maintains a home with his spouse Terrence Flannery.

An added bonus of having covered the five-time Grammy-nominated entertainer, who is celebrated as the Ambassador of the Great American Songbook has been the great pleasure I have enjoyed seeing Flannery, a cherished friend, on a regular basis, all these years. It’s a friendship that began in 1987 when Flannery lived in Indianapolis, where the two of us first met long before he became the husband of one of the most renowned performers in the world, and with whom he has shared a life filled with many rarified experiences.

Introduced by mutual friends, Flannery and I had much in common, including our professional interests. At the time, he was the successful owner/operator of several nursing home facilities, and I was employed as a producer/director at WRTV-Channel 6. A native of Portsmouth, Ohio, Flannery earned a degree in Telecommunications in 1981 from Indiana University, so naturally he had an interest in broadcasting. Over the course of time, he eventually moved to Chicago prior to relocating to Los Angeles. All the while he and I stayed regularly in touch.

In 1997, Flannery was in LA, and we spoke by phone, during which he shared that the night before he had attended a Hollywood party hosted by producer Craig Zadan (“Footloose,” “Chicago,” and “Hairspray”) where he met Feinstein. I recall at the time how amused I was that Flannery, who at the time did not have much interest in the entertainment industry, knew so little about Feinstein. Ultimately, Flannery’s guilelessness and lack of ulterior motive worked in his favor because eventually he and Feinstein were wed in 2008.

As mentioned previously, Flannery and I maintained contact and managed to visit with one another a few times in New York, but once he began travelling with Feinstein, it became increasingly difficult to spend any quality time together, especially when they visited Carmel where their schedule was packed with meetings and obligations. Flannery is a founding board member of the Songbook Foundation and is actively involved in all business matters related to Feinstein’s career.

After learning that Flannery was in the Carmel area with Feinstein for a week following the star’s Judy Garland concert, I reached out.  It occurred to me that, given our long history, who is better than yours truly to profile my dear friend, a success in his own right who has always forsaken the limelight as he has journeyed alongside one of the world’s most celebrated artists?  Prior to the interview, we caught up at lunch at Vivante French Eatery in Hotel Carmichael then moved to a quiet space adjacent to the main dining room for the interview itself.  Below is an edited transcript of my conversation with Flannery.

Terrence Flannery & Michael Feinstein – Courtesy of The Center for the Performing Arts. Used with permission.

In a nutshell, how would you describe your 26 years alongside Michae Feinstein?

Having a relationship that long and maintaining the intimacy and closeness we’ve had all those years has been our reality. When you travel with someone 24 hours a day on the road, it can be a challenge. The road becomes your home.  It is remarkable to find somebody you can live with in that manner.

How did you learn to adapt to life on the road?

Oddly enough, it wasn’t difficult because we had a commitment and a desire to be together, so that was the driving force. When you have that in your life, obstacles become opportunities to get around certain things and help you grow, especially if you have a focus to be with someone.

These days travel is certainly not easy. It sounds like you make the best of it.

No, travel isn’t easy. You have known me for so long and are aware that I am a people person. I love my friends, but you are forced to sacrifice sometimes. When you are home for three days, and your friends aren’t aware of it, you don’t get invited to parties. It can get a little lonely. People presume that we are in the most amazing places on the road, all over the world, and sometimes you lose contact with people you love and are close to.

Even when you are on the road you are constantly working, right? Aren’t you always planning ahead?

Yes, you are constantly booking and planning three years out.

As a member of Michael’s team what is your job description?

My job is being a spouse. Everyone has a role in a relationship. In ours, I take care of the finances and handle business details. Michael handles the artistic duties. I try to do as much as I can, so he can focus on the artistic and not have to deal with the finances and bills. Those are my responsibilities and what I handle.

I have always known you to be very successful at business. Did you bring that acumen to your relationship?

To a certain extent, yes. I do not manage him, but I try to handle the business end of his career, interacting with his managers and contributing my experience and skills. Interestingly enough, some of that does not always translate. The entertainment business in many ways is so different from the traditional business arena. I would go to agents and say, “Here’s where Michael has sold out 50 venues in the last two years, so let’s call those venues and prepare for the next tour.” And they would reply, “Well, we have 10 clients. If we do that for Michael, we have to do that for all our other clients.” As a businessman, I thought, “Well, if I owned the agency, I would think it is a pretty good idea because you could increase your business and your gross as an agent, but it doesn’t happen that way. They wait for the phone calls to come. I don’t want this to come off as trashing agents. I am not. Sometimes, however, I’ve felt like I was hitting my head against the wall suggesting things I felt were just good business practices.

Surely you have brought your management skills to the fore helping Michael with his career, right?

Artists are looser in the way they handle things. He doesn’t have the time to do some things I handle.  When I am doing things, I inform him. He is very, very smart. He gets it, and I don’t have to explain everything.

As an observer, ever since you and Michael became a team, both literally and figuratively, his career seems to have blossomed.

I don’t know what would have happened had we not entered each other’s lives. He gives me what he has, and I give him what I have, and together we’ve become a very powerful team. We both feel it and know it, and people around us know it, too. Whatever that combination is, it has exploded.

When it comes to you as a married couple, trust counts for a lot, doesn’t it?

It really does. There is so much that goes into trusting one another when so much is going on. You have to trust that the other person has your back, and that is powerful. Things are constantly changing in show business. It seems positive, but it can turn on you. It’s difficult sometimes. There are more checks and balances when you are with someone you trust. We are both so different. What I love is that we both view things so differently. When you have two perspectives, sometimes it is the combination of those perspectives that help make decisions.

What do the two of you disagree on?

Oh my gosh. Here’s an example. He and I are both from the Midwest, but we are very different. Michael is very, very honest. He is black and white. I’ll tell a white lie when I don’t want to hurt someone’s feelings. I never lie to gain power or manipulate, but sometimes I just want to avoid making an issue of something. He’ll confront me and say, “You just lied” and get so angry with me. (laughs) He is very literal, and it is lovely. I love that quality in him, but for me it is innocent, and sometimes though intended to be innocent, I tell white lies. (laughs)

Is it fair to say you differ in style?

It’s style, but he calls it lying. (laughs)

You have had a rare backseat to enormous fame during your time together with Michael. What are the upsides and downsides of fame?

I have tried to stay clear of it. I don’t like having my picture taken. I am fine with letting him have all the attention. I am uncomfortable if I must speak in public. I much prefer taking a back seat. When I was younger, famous people in show business never interested me. I was interested in sports. I never watched TV, so when I met individuals, such as Liza Minnelli, Rosemary Clooney, Sandra Day O’Connor, or Nancy Reagan, we would go to dinner, and I didn’t have any preconceived notions. I was just meeting Michael’s friends. Before I met Michael, we both were in our own worlds. I had my own company, and he had his career.

Given your lack of awareness of celebrities before Michael, what is it like now?

Creative people are interesting. They are different. They take left turns, so life is very exciting.

So you are not jaded, and it hasn’t gotten old?

It’s just gotten better because you are always around stimulating people. You go to a Broadway opening, and you go to the party afterwards like to one we just went to see – we saw Sean Hayes in a play about Oscar Levant (“Good Night, Oscar”). I remain grateful for all the friends and connections I have made in the entertainment world. It’s made me a better me. The experience has made me see the world differently and view my own life differently. I am with someone who is so unlike me, but it so challenging in a good way and makes me think, “Oh, I can be a better person.” If I am willing to be vulnerable. It has been an amazing opportunity to change.

How has your marriage to Michael and being surrounded by artists and their art influenced you over the years?

I am surrounded by brilliance every day. And before I met Michael, I never had idols, but if I did look up to someone, it would be a CEO.  I jumped into a world with him, and now I am around brilliance of a different kind. It’s not the journey I imagined for myself.

What are your and Michael’s team goals?

Our goal is to work as long as we can. We are working right now on licensing his brand. Some of that will involve home furnishings and men’s apparel. We have already done some deals. Michael has millions of fans, and we have never tapped into that. As we grow older, we want to spend less time on the road doing shows. We are on the road 200 days out of the year.  Kathy Ireland has taken over our brand and is now our partner. She has started a company with us and is doing the licensing for Michael.

Any creative projects you two are working on?

We are doing an album with pianist Jean-Yves Thibaudet, and preparing to play our show “Two Pianos: Who Could Ask for Anything More?” with the legendary Boston Pops.  Later, we will tour with classical orchestras. It will go around the world for three years. We are constantly moving and changing. That’s one of the reasons Michael is relevant today. A lot of young people know him from the clubs and the Songbook Academy. We did not strategically plan that. We just followed our hearts.

What is your involvement behind the scenes with the Feinstein’s clubs in New York, San Francisco, and Carmel?

I work closely with John Iachetti and Michael’s management team in the licensing deals and responsibilities that come with the Feinstein’s clubs.

Tell me about your investment in the Great American Songbook Foundation and the Songbook Academy.

The Academy is our passion. We have tried to give back to young people, who are finding their way in the world and may have no opportunity to be seen or heard. Having kids from 50 states and having this foundation for 10 years has been a total blessing. I have always wanted kids, but Michael hasn’t because we are on the road over 200 days out of the years. Looking back, we probably wouldn’t be together now if we had a couple of kids because I would have stayed home and wouldn’t be on the road with him. God had a different plan. We are like parents now. (laughs) We get calls requesting recommendations for students who need to get into college and other things, and so it is a beautiful thing. They become successful and are happy. I never thought we would be parents, but we really are (laughs). My proudest moments have been with the Foundation and working with students across the country. I have learned so much in the last 10 years working with such beautiful young souls.

What are your thoughts about the proposed Great American Songbook  Hall of Fame museum for which site selection is now in progress?

I am thrilled that the future museum will be in Indiana. The world knows America through its music so having this international attraction in Indiana will be major. I wouldn’t want it in any other place. The Midwest is the perfecct place for this museum.

Do you still experience “pinch me” moments? 

I was a kid doing barrel racing while growing up and then later got into health care and created a good life. I enjoyed every element of my life, but I always wanted more. Not so much in a material way — I just knew there was something more for me. I am so grateful for my life now. I am so grateful to have Michael as my spouse and for what we have accomplished together. I wish my mother were here. We were so close. She died young. She is still on my mind. She would be so proud.

Do you find it ironic that you now have a presence, not to mention a home, in Carmel in Central Indiana where you once lived?

Life often circles around and brings us back to the same place, and it is up to us to come back stronger and healthier. I think I have done both.

Describe Michael Feinstein the man and the artist?

Michael does not define himself by what he does. He lives in music both personally and professionally, so he is the same person. Music is his world, so I just have to accept the positive and the negative that comes with it.

How do you wish to be remembered?

I truly have no desire to be remembered. I feel this is my time now, and I need and want to make the most of it.





photo: Josh Humble

About Tom

Journalist, producer, director, Emmy Award-winning documentary filmmaker, arts administrator, TV contributor, actor, model, writer and lyricist, Tom Alvarez has had an extensive career in media and the fine arts and continues to be an enthusiastic and devoted fan of both. His passion and unique background grant him insight, access and perspective to cover, promote and review the arts in Indianapolis, Central Indiana and beyond. Follow him on social media @tomalvarezartswriter and @tomalvarez1.

Alvarez has been writing about theatre, dance, music, cinema and visual arts for 40 years. His work has appeared in the Indianapolis Star, NUVO, Indianapolis Monthly, Arts Indiana, Unite Magazine, Dance Magazine, NOTE Magazine, and Examiner.com, among many other print and online platforms. A former contributor to Across Indiana on WFYI-TV, he currently has a regular performing arts segment on WISH-TV’s Life. Style. Live!

A principal of Klein & Alvarez Productions, LLC, Alvarez co-created “Calder, The Musical” and is the managing director of Magic Thread Cabaret. As an actor-model, he has appeared in numerous TV and print ads and is represented by the Helen Wells Agency and Heyman Talent Artists Agency.

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