Interview: Ann Kittredge's WHEN IN LOVE at Chelsea Table + Stage Gets Intimate

On Thursday May 8, 2025, award-winning vocalist Ann Kittredge returns to Chelsea Table + Stage with a new show, When In Love, featuring pared down and intimate musical arrangements, “an evening of joyous revelation and heartfelt introspection, the kind of a program that can only be done by… two.” The singer is fresh off her 2025 Bistro Award win for her recent album, Romantic Notions. We spoke about her upcoming show, holiday album and more.

What are you looking forward to about your upcoming show at Chelsea Table + Stage?

This will be my first show with just Christopher Denny at piano. Chris and I be bringing romance to our audience! Woohoo!!! And it has been a real learning experience with Chris and my director Barry Kleinbort to put together a program that is textured and entertaining and that perfectly suits the simplicity of piano and voice. How Chris can sound like an orchestra at times is thrilling!

Where did you get the idea for the show from?

Truth be told, Stephanie Lewandowski reached out and invited us back after doing a few shows at Chelsea Table + Stage last year. We HAD to say yes because we love working together, but when Barry and Chris and I first sat down, we had no idea what direction to go. We wanted to challenge ourselves — that’s always a given — but we also wanted to highlight the story-telling of the music, similar to the olden days of nightclubs. I am a true romantic at heart and we all felt we had a lot more to say on the subject. When we decided to include a specific song from my Broadway debut — King David (Alan Mencken & Tim Rice), I found my title — When in Love. From there we put together a program that highlights the vagaries of human emotion, especially that pesky thing called love, along with culling together a selection of music that visits diverse styles and time periods.

What do you want audiences to get out of WHEN IN LOVE?

We are particularly excited to share the variety of musical styles and genres and time periods that all speak the language of love in their own unique way. Our song selection includes music written over 100 years. There are gems at any age! And some gems, when we bring them to 2025, can be heard and experienced differently without losing the essence of what made it a hit way back when.  

How did it feel to be honored with a Bistro Award last month for your Romantic Notions album?

Ha! Can I tell you, I was soooo nervous the day of, it took me a while to just get out bed, then I stretched for an hour, and oh so slowly got ready to arrive early for tech rehearsal.  Even though I’d sung the song I did that evening many times by now, I was convinced I was going to flub the lyrics (I didn’t; yay!), so I kept sneaking away into corners to practice.  Then, when they called my name and I got up on the stage to sing, something magical happened amongst Chris Denny, who was at the piano, Rex Benincasa, who did the D&P for Mr. Tambourine Man in the recording and at live performances, and the new man to our troupe, Ritt Henn, and me. There was a freedom and a connection to our performance that was fresh and exciting. We felt the audience was with us, it was a memory for the ages for me. I was sincerely honored. And what an evening Sherry, Gerry, Mark and Mary put on. Sidney Myer’s glorious and distinct voice leading us through the evening, not to mention Jerry Seinfeld showing up! I felt well cared for and so, so grateful.

Can you tell us a little bit about your upcoming holiday album?

We are in the final stages. We finished recording mid-April. We have the title, You Sleigh Me, and my graphic designer, Lisa Daniel Rees has done it again with her design for the album.  The title makes me smile, the songs we chose are pretty mainstream Christmas with the Ann Kittredge twist, and one song we released a couple years ago, we are including an extended version on the album. I’m eager to see how people respond to it.

Aside from your holiday album and CT+S show, what’s coming up next for you?

There are some wildly exciting things coming down the pike that I wish I could tell you, really, but my lips are sealed. I can tell you that I’ll be part of Stephanie Lewandowski’s Mother’s Day show on Sunday, May 11 at 1 pm, also at Chelsea Table + Stage. I’m teaching 5th graders at a public elementary school in Queens to prepare them for their graduation through the ASA education program. I’m doing this with the wonderful, talented and true sweetheart, John Cook. I know I’ll be returning to Puerto Vallarta sometime and I’m working on other bookings. There also may be a legit theater production down the road a bit. Fingers crossed.

Is there anything else you’d like to add?

I feel so lucky. I have people surrounding me that I trust and that we’ve developed a really rewarding creative relationship together, Chris, Barry, Paul Rolnick, Randy Klein (President, Jazzheads Music), Rex Benincasa, Mary Ann McSweeney, Ritt Henn, Aaron Heick, Tom Kochan. And what I particularly love about each of them, is when we're working together, everyone is ready to contribute. Some great arrangement additions have occurred at the band rehearsal, or even sometimes at the recording session itself! We trust each other, and they bring me such joy. As for performing live, I am grateful for every person who decides to spend their money and time expecting me to entertain them. Looking forward to seeing the faces of my audience is such a high, such a drive to get there. I guess what I’m saying is, I am really lucky. We have a great show coming up for our audience on May 8. Can’t wait to see you!

Header Photo Credit: Gene Reed

Learn more about Ann Kittredge on her website at www.annkittredge.com