Photo credit: Conor Weiss
Ann Kittredge on Artistry, Community, and the Meaning of Recognition
In the intimate world of cabaret, authenticity reigns supreme—and few artists embody that truth more fully than Ann Kittredge. Fresh off her 2026 MAC Award win for Best Female Vocalist, Kittredge is energized by collaboration and deeply committed to the craft of storytelling through song. In this candid conversation, Kittredge opens up about artistic evolution, the power of a creative team, and why the connection with an audience will always matter more than any accolade ever will.
Q: Winning the 2026 MAC Award for Best Female Vocalist is a major milestone. What did that moment mean to you personally?
It was really lovely—and awkward. I struggle with the idea of comparing artists as if one is “best” rather than just different. I knew most of the women in my category, and they are incredibly talented, so I was ready to celebrate them.
I’ve been reluctant in the past to even put myself out there for this award because, truly, my audiences are my reward every time I get to go on stage and entertain them. That said, it’s meaningful to know that people in your field appreciate what you’re doing enough to vote for you. I’m sincerely touched and grateful.
Q: Your award recognizes a body of work across your album Romantic Notions, your show When in Love, and your single “You Sleigh Me.” How do these projects reflect where you are artistically right now?
It took me a few years, but I now feel like I have the best creative team around me—people who are masterful in their own right and who truly understand my talent. They challenge me in the best ways.
What we’re creating together feels like a true reflection of who I am. We love exploring the quirky as well as the deeply emotional. I get bored doing the same thing repeatedly, so keeping things eclectic is the way to go for me. The surprise, the depth, the silliness, the irreverence—it’s all part of the joy of sharing.
Q: Your performances at venues like Chelsea Table + Stage and Act2PV in Puerto Vallarta have connected you with very different audiences. How have those experiences shaped your approach to storytelling?
Oops. Was I supposed to change my approach based on the primary language of my audience? Dang, I have work to do!
O.K, to answer your question, every show is different because every audience is different—and I’m different each time, too. But I don’t think language is necessarily a barrier to entertaining people. Storytelling doesn’t always require shared language. Opera has thrived on that idea for centuries. I’ve seen audiences respond deeply to stories told in languages they don’t speak, simply because the emotion is genuine.
I remember performing “Besame Mucho” in New York. At first, there were a few giggles—maybe uncertainty. But within a couple of lines, the room shifted. The audience leaned in. By the end, the response was overwhelming. That moment reminded me that storytelling transcends language when it comes from the heart—or even the funny bone.
Q: Was there a moment when you realized this chapter of your artistry was something special?
Finding my creative team was the shift. You don’t know what you’re missing until you have it.
Over the past few years, I’ve gotten better at letting go during performances and simply being present. That confidence comes from trusting my collaborators—my music director, Christopher Denny, and my director, Barry Kleinbort.
They’ve encouraged me to trust my instincts, and sometimes I think they now regret that because they’ve helped to build up my own creative confidence to push back more when something they suggest doesn’t feel right. And honestly, that back-and-forth is where the magic happens. We all feel it when it’s right.
Ten years ago, I worried I’d run out of ideas. Now it’s the opposite—I have more ideas than I can keep up with. It’s an exciting place to be.
Q: What does it mean to be recognized by your peers in such a close-knit artistic community?
I was sincerely moved. I love this community. I’ve made incredible friends, discovered amazing music, and been surrounded by people who share a deep passion for what we do.
What’s special is that no one tries to dictate what I should bring to the stage. Instead, there’s support, inspiration, and mutual respect. That acceptance is incredibly validating—and I’m deeply grateful for it.
A Continuing Journey
In a world that often measures success by accolades, Kittredge offers a quieter, more enduring metric: connection. And if her recent work is any indication, that connection is only deepening—with every note, every story, every joke, and every stage she steps onto next. Learn more about Ann Kittredge at:
