We caught up with the brilliant and insightful Ann Kittredge a few weeks ago and have shared our conversation below.
Ann, thanks for taking the time to share your stories with us today It’s always helpful to hear about times when someone’s had to take a risk – how did they think through the decision, why did they take the risk, and what ended up happening. We’d love to hear about a risk you’ve taken.
It is a creative risk. As we were putting together my last album, “Romantic Notions,” I decided to allow the term “notions” to permit me to expand beyond just the human-to-human relationship and include songs that found romance in other facets of life, like a view or an idea. How my creative team works is that we all shoot out ideas and from there decide together if it fits our vision. Lots of songs are rejected in the process. I was particularly interested in finding a love song to music itself. I landed on “Mr. Tambourine Man.” Though my creative team initially struggled with this idea, I found I couldn’t let it go. Over several months I kept bringing back the song with arrangement ideas and my team was still reluctant. Finally, I wrote them and told them that, though I really appreciate their concerns, this song was resonating with me to the point that I needed to record “Mr. Tambourine Man.” If it was a flop, I’d take total ownership. I also told them that if they couldn’t in their hearts work on this with me, that was O.K., I’d find someone who liked the idea. I had NEVER fought for a song before, I always relented. But something about this song made me persist. My team graciously accepted the challenge. I LOVED what we found, but I also knew it might be jolting to Dylan fans and may not be welcomed. It was so important to what I wanted to say, though, that I stood by the decision. Ends up our arrangement was very well received. It was a huge moment for me to stand up for something only I believed in, and convince my team to stay with me on it.
Ann, before we move on to more of these sorts of questions, can you take some time to bring our readers up to speed on you and what you do?
I graduated from Carnegie Mellon University and then moved directly to NYC, This city has been my landing pad for the majority of my life. I quickly got my union cards and was travelling the country working at regional theaters, as well as getting local gigs off-broadway and off-off-broadway. Eventually I played featured guest roles in TV series’ being produced in NYC, as well as a couple stints on Broadway. I supplemented my income for the first 10 years or so working as a temp for law firms. At the time computers were fairly new and so if you had skills, you could make good money. I had skills!
About 2 years after my second child was born, we decided that I would stay home and be there for the kids. My income was about equal to paying a nanny, and it didn’t make sense to me, So, though I NEVER saw myself doing this, I decided to stay home with the kids until they started school. What I thought was going to be a 4-5 year pause on my career ended up being an 11 year pause. I found that I had a lot to offer the public school system and became an education advocate and volunteer. My goals were to provide value for the students, contribute to their arts programming, and build community in- and out-side the walls of the building. It was incredibly rewarding, I felt like I was modeling for my children the value of volunteering and working for the benefit of all, not just them. As the end of my son’s middle school years was nearing, I pretty much burned out, and I also realized that I really missed performing. After 11 years, though, could I still do it? I decided to step back into the entertainment business via cabaret — a genre I had never done before but would provide me creative freedom and a platform to test out my music skills after all those years. Cabaret is a very specific art form. The experience of doing 8 shows a week on a proscenium stage with theaters averaging 500-2000 audience members for 16 years was not compatible with cabaret. Cabaret is an intimate art form set in small venues, and as such requires different competencies, such as: you don’t need to project to the back of a large theater, and you don’t have a character to hide behind because cabaret is about sharing yourself. Being yourself can be harder than creating a character on stage. So, this art form was going to be a challenge. Surprisingly (truly), I won an award my first year for my debut show. Shortly after that the pandemic hit. In our isolation I created a youtube series, “Virtual Shorts” that provided live performances to our audience’s homes with no latency issues, based on a new program called JamKazam. It attracted press and was well received. I also spent the isolation teaching myself how to edit film, audio and photos (I’m so proud of this. I do most of my graphics work for my shows and marketing). As the world was beginning to open up, I suddenly had an urge to record a few songs from my shows whose arrangements I particularly loved and I wanted to preserve them for my kids. I had no intention of monetizing it. It was just going to be a gift for my kids. However, as I looked for people to help me figure out the logistics of getting rights to record, etc, I met a producer/mixer who changed the trajectory of my life. He seemed truly excited about the recordings I had already done and seemed sincerely excited to work with me. It was such a validation. He held my hand through the whole process, and then he made me dream bigger. He thought I had something to say and he helped me get that album seen. “reIMAGINE” (released May 2022) was picked up by a record label, Jazzheads Music, and it won a LaMott-Friedman award. It did so well streaming that the head of Jazzheads, Randy Klein, encouraged me to get back into the studio and take advantage of the momentum. That’s how “Romantic Notions” (released May 2024) came about. It won a 2025 Bistro Award and was picked as one of the top 10 albums released in 2024 by the Broadway Radio station. That led to my next release coming at the end of this year, a holiday album called “You Sleigh Me.” In the meantime, I’ve had the honor to perform at major music venues in NYC, including 54 Below and Birdland, as well as locations around the country, and even in Puerto Vallarta, Mexico!!! I think what I’m most proud of is that so many critics and fans are appreciating my storytelling and creative bent. I’ve been called a singer-songstress supreme — Ha! — and it is often pointed out that I bring fresh perspectives to any song I choose to interpret. That means a lot to me.
Something I’m most proud of that was also really difficult? Well, I guess most recently it was something that happened just last year. On May 11th my mother passed away in our home. She had Alzheimer’s and was 97. I was so grateful to have the opportunity to care for her through her end-of-life. Just 4 days later I was scheduled to release my “Romantic Notions” album at a sold-out performance at Birdland. Being old school, I felt I had to fulfill that obligation, which I did. It was one of the most difficult performances I’d ever done. What made it rewarding was knowing that my creative team was SOOOO there for me, holding me up with their love and care, and the audience was none the wiser, until the very end when I announced that my mother planned to be there, but she decided she wanted a skybox for this one. Then I paid tribute to her by handing out “Hug Coupons,” something my mother was famous for giving out. They point out all the positives a hug gives you and that they are redeemable. My children and my husband were there to cheer me on. It was a very special, meaningful night.
I’m proud of many things, my marriage, my children, my music, and especially, I love my creative team. Over just these past 3 years we have become a family.
While volunteering, I did a lot of vocal teaching and coaching for free. My voice teacher is the world-renowned Adrienne Angel, and she so wants me to teach some day. I appreciate her belief in me and I think I’d like that, too. It is a joy to share my love of music with others.
Before every show, every creative endeavor, I think about my audience — how do I serve them, what kind of escape can I give them, how is their day going, what do they need? I love my audiences and I know they are trusting me with their time and their desire to be entertained! I feel very lucky.
Is there a particular goal or mission driving your creative journey?
My particular mission is to create value through my interactions and my music. Art is essential to a fully realized spirituality. It can be healing, distracting, relaxing, energizing. I believe it is my role as a human being to contribute to the forward motion of being a compassionate, productive human being.
Learning and unlearning are both critical parts of growth – can you share a story of a time when you had to unlearn a lesson?
I had to unlearn that I wasn’t good enough, that my creative approach was unwelcomed and weird or just unacceptable. It has taken a long time to build the confidence to be true to myself as an artist. As I mentioned before, creating and bringing to life a character is something for which I was trained, and really thrived in doing. To think that an unmasked me can be as entertaining if not more so, was impossible to believe for a long time.
Contact Info:
- Website: https://www.annkittredge.com
- Instagram: @annkittredge
- Facebook: https://www.facebook.com/AnnKittredgeHappenings/
- Linkedin: https://www.linkedin.com/in/annkittredge303/
- Youtube: https://www.youtube.com/@AnnKittredge
- Soundcloud: https://soundcloud.com/annkittredge/sets/romantic-notions-1?si=49dd49497c05441296736fa2b92f73c8&utm_source=clipboard&utm_medium=text&utm_campaign=social_sharing
- Other: https://www.promarketing.team/annk
Image Credits
Gene Reed, Takako Harkness, Conor Weiss, Mary Ann Lopinto