Interview: Singer-Songwriter Ann Hampton Callaway Brings Her Best to 54 Below

From Wednesday September 24 through Saturday September 27, catch The Best of Ann Hampton Callaway at New York’s 54 Below. The show features highlights from the Tony®-nominated singer-songwriter’s recent hit shows including The Streisand Songbook, Ann Hampton Callaway Sings the ‘70s, The Linda Ronstadt Songbook, To Ella with Love, From Sassy to Divine: The Sarah Vaughan Project, and Finding Beauty: Inspired Classics and Originals.

We spoke with Ann Hampton Callaway about the upcoming show, her new songs, and what she’s been working on lately.

This conversation has been edited and condensed for clarity.

Can you tell me a little bit about this upcoming show at 54 Below?

I've taken highlights from my recent hit shows. Many of these shows are legacy shows: for instance, a tribute to the great Ella Fitzgerald, who was my first favorite jazz singer; Sarah Vaughan, Barbra Streisand, Linda Ronstadt. Then I do a show of the 70s: the singer-songwriters like Carole King, Joni Mitchell. These are people who woke up my understanding of what I wanted to do with my life, to not only sing, but to also write songs from the depths of my heart. I also have a recent show called Finding Beauty: Inspired Classics and Originals. So, people will hear a few well-chosen songs from my latest CD, which debuted number one on iTunes Jazz.

So, what I've done is to try to create a well-balanced program of exceptionally beautiful, powerful songs that resonate to me as a human being during this time we're living in. Songs that I need to sing, songs that express different sides of who I am. And I get to tell kind of a story of what matters to me and have some fun with the audience, etc. I will also be doing an improvisation, which is one of the signature things I enjoy doing in performance as well. I'll take words and phrases from the audience and create a song for Barbra Streisand's next album, so to speak. That is kind of a reference to the fact that my songs have been on seven of Barbara's recent CDs.

And so, people will hear songs from Ella Fitzgerald, Sarah Vaughan, Linda Ronstadt, Barbra Streisand, Joni, Carole. It will range from pop to jazz to Broadway and my own original songs that sometimes defy description. I don't really like to be pigeonholed. I'm a person who has a broad reach musically and emotionally, and I'm also a storyteller, so I'll be enjoying telling stories to the audience that are helpful doorways in making these songs come alive even more.

And I'm excited to be returning to 54 Below, which has been the home for so many of my favorite premieres of these shows. And the audiences have always welcomed me so warmly and it always feels like a joyous homecoming to return to New York and to get to perform in such an intimate, beautiful space, and also do a livestream [on Saturday September 27] for people who can't be there.

You’re also doing another show at 54 in January called Here’s to Life. Can you tell us a bit about that show?

That’s an APAP show. APAP is a convention where people from all over the country, and sometimes parts of the world, come to hear someone's new show. And I'm actually in the process of putting that show together. The theme of the show is looking at life through the lens of what matters to me and finding songs of exceptional beauty and wisdom that reveal how I feel and what I've learned in my life.

Here's to Life is the title song of the show, which I think is one of the most gorgeous songs ever written, written by Artie Butler. I will be doing a combination of great American standards of the highest level of beauty and intelligence, and songs that I've written that really kind of tell the story of what I've learned in my life.

And as I said, it'll be an interesting combination of the Great American Songbook, pop songs that I grew up with feeling that they have something personal to say. So, it's going to be a very personal show of working on creating a portrait of how I feel and what I've learned in my life, so look forward to hearing the surprises that will await us all. I wanted to make sure it's a really special show that I'll be doing throughout 2026.

And I'm also going to be recording a record with Shelly Berg, the great jazz pianist with that song title. I'm not sure when that's happening yet, so I thought this was a good chance to really dive into that project.

But in the meantime, I have so many things I'm working on right now, including an upcoming recording project with Melissa Manchester, writing songs for that. So, I will in the next few months be finalizing those songs and perhaps we can talk again.

What have some of the biggest surprises of your songwriting career been?

I met Fran Drescher in 1987. She came to one of my shows at Don't Tell Mama. I didn't know who she was. She’d made a film or two, and she was very charming to me. And she came with my sister’s costar when she was on Broadway. Anyway, I met her. She loved my songwriting. I did that show of original songs. And I never dreamed that... After all the little pilot themes that I wrote for her, when she called me one day and said, “I'm doing a pilot for a show called The Nanny, I'd like you to write a theme song for it,” I thought, oh no, another expensive demo. And little did I know that it would become not only a huge hit that continues to this day to be aired all over the world and is one of the last real TV themes. When I wrote that song, I had no idea it was going to be a show. I had no idea it would be syndicated all over the world. I had no idea that it would be still on television here in 2025, and that it would have such an impact. Even on CNN, they talked about that being one of the most important TV themes in television history. That was a huge surprise to me, and I'm so grateful for my friendship with Fran Drescher. She's an exceptional woman and a dear friend. That was my first big break as a songwriter.

Then, my next big break was getting to have the peace anthem that I wrote, called "At The Same Time" [featured on Barbra Streisand’s album]. I sent that to her in many, many ways and it took ten years to the date that I wrote the song for her to do her final vocal on her album, Higher Ground. And being the daughter of a famous journalist in Chicago, John Callaway, I have spent my whole life being very concerned about world peace, and I wanted the song that I had written to be shared with millions of people.

And Barbra did share that song. It was just an unprecedented moment in my songwriting career. Then, because she really liked my lyrics... She fell in love with a melody by Rolf Løvland, who is the songwriter for the Secret Garden. She wanted me to write a love song because she had met the love of her life, James Brolin. And so I wrote the words to what became her wedding song, “I Dreamed of You,” and that was another multi-platinum hit that was one of my favorite love songs I've ever written. And the fact that she loved the song so much she wrote about it in her autobiography really touched my heart.

I got to write them some specialty material for the Broadway show Swing that I starred in on Broadway. It was exciting to be able to work in that world. I've written hundreds and hundreds of songs that have been on numerous recordings. I recorded one of them with the great Carole King, who was the reason I am a songwriter. She wrote a song with me in the studio the day of the recording and then taught the band a few hours later, stayed and sang backup vocals. It was just one of the happiest days of my life.

Recently, for my newest CD, Finding Beauty, Originals, Volume 1, I got to write with another favorite singer-songwriter, Melissa Manchester. We wrote a song called “New Eyes,” and we recorded it together, and it was a thrilling experience.

And I'm currently writing a song with her right now that I think is a very important piece. It's called “Audacity,” and I think it's going to be an exciting, inspiration for people in our time. We'll be recording that on an album with the DIVA Jazz Orchestra.

But I've also written songs for the numerous challenges we've been through. I released a song called “Carry On” during the pandemic. After 9/11, I released two songs. One just became released on Spotify called “Let Us Be United.” And another one is one of my newest singles called “I Believe in America,” which I wrote right after 9/11. And I tried to address the world that we're living in, and I tried to find a way to uplift people, inspire people, and give some insight into what we go through as a culture.

So, it's a very thrilling thing. Very recently I was inducted into the Women Songwriters Hall of Fame, and I'm hoping to do a lot more writing. I hope to do much more to inspire people and to try to bring art into the world that can bring us together. There's just so much that we're going through in this time. It's time for the artists to rise up and to really give our all to this new insight into how we can live together, and how we can help our planet and how we can help our country thrive.

How do you feel like your songwriting work has evolved looking back at the past 5 years of your work?

That's an interesting question. I'm going to give two sides of that answer. Back in the day, in the 90s, when I was releasing songs through artists like Barbra Streisand, and The Nanny, the whole world of music was entirely different. We songwriters were being taken seriously business-wise. We were paid well. We were given the value of what we did.

Now that streaming has taken place, a lot of recording projects feel like, “Okay, well, I'm writing this song because I care about something,” and I don't have any real faith, honestly, that millions of people will hear these songs now, unless some miracle happens, because the world of, of, the music business has really atrociously stripped artists of their financial benefits, intellectual property value, and it's very hard to be heard at the same level. It's hard to make an impact. However, I don't do things to be famous. I don't do things to have hit songs. I do things because I need to do them, because I care about something, and because I feel strongly about things.

And I will say that in the last five years of my life, I feel I’ve matured a lot as a human being. I feel like I've learned a lot. In 2020, I started writing a poem every single day and publishing each poem on Facebook and Instagram, and then I continued on for another year. And several of the poems turned into songs, and I'm still working on a number of poems from that very rich time when we were so scared to death, like, are we going to live? What's going to happen [to] the life we know? Are we going to be able to make a living? It was a terrifying time and yet it was also a beautiful time because it gave me time to think and to be creative and to make a record slowly. And so that was a very rich time to just focus on what mattered to me as a writer.

And I have a very exciting project I'm not at liberty to discuss yet, but hopefully, later in the fall, I will be able to talk about this. It’s a dream come true. So, I hope that all the things that I've learned about as a songwriter and the people that I've gotten to work with, I hope that that will ready me to do something really exciting, that I will talk about in the near future.

Is there anything else you’d like to add? Any other new / upcoming projects you’d like to plug?

As I said, I'm doing a record with, Melissa Manchester. It hasn't really properly been announced, so you might be the person who's breaking the news. I'll be recording with the DIVA Jazz Orchestra and Melissa, and we had a fabulous time. She came to my home a few weeks ago, and we just got down to business and created some really exciting arrangements. We're zooming today to finish up a song that I'm very excited about.

So that's the biggest project I can talk about right now, and the other project is enormously exciting, but I'm not at liberty to say what it is.

And I have a very busy touring schedule. People can find out where I am on AnnHamptonCallaway.com and social media. They can also find me on Patreon where I've been sort of creating an artistic inner circle and sharing things for the people who really care about all things Ann Hampton Callaway and the deep listeners and the deep fans.

I keep trying to sing and write and do performances, create songs that will address this time and this world that we're living in right now. And I'm very concerned about where things are going, and I hope that my presence as an artist will be something that offers people hope and inspiration.

Learn more about Ann Hampton Callaway and where to follow her on social media and Patreon on her website at annhamptoncallaway.com