CONVERSATIONS|PicksInSix Q & A - Liz Callaway
To Steve With Love: Liz Callaway Celebrates Sondheim
CONVERSATIONS|PicksInSix® Q & A | Ed Tracy
Liz Callaway returns to her hometown of Chicago for a one-night only concert performance of her Grammy-nominated album “To Steve With Love: Liz Callaway Celebrates Sondheim” at the Studebaker Theater on Saturday, June 14, 2025. Recorded live at 54 Below in New York City and released in November 2022, “To Steve With Love” weaves personal reflections and entertaining stories about Callaway’s professional career with intimate touchstones and featured performances from Sondheim’s extraordinary songbook.
Callaway’s Broadway debut in “Merrily We Roll Along” launched a string of stellar theatrical roles—and established a forty-year association with Stephen Sondheim—that included, “Follies,” “Baby” (Tony nomination), “The Spitfire Grill (Drama Desk nomination),” Sunday in the Park with George,” “Evita,” “Miss Saigon” and acclaimed animated Disney projects including “Anastasia” and “The Swan Princess.” A busy concert schedule, that often includes memorable appearances with her sister, Ann Hampton Callaway, has taken Liz Callaway to intimate cabaret clubs and major concert venues across the U.S. and abroad.
In advance of the Studebaker show—her first performance here in recent years—Liz Callaway joined in an email exchange to share some thoughts about the development of the show, the impact her parents had on her music career, and some essential advice for early career vocalists about Sondheim’s songs, all from one of the finest pure singers working today.
Ed Tracy: It’s been a minute since you were last in Chicago. It must be exciting to return home to familiar territory, old friends and a community where the Callaway’s—your Dad, John, sister Ann and you—have such a longstanding presence. How are things coming together and what’s on your Chicago agenda while you are here?
Liz Callaway: I’m counting the days until I come to Chicago! I’ve wanted to do my Sondheim show in my hometown for so long—in fact, it was at the top of my New Year’s resolutions—and I’m so thrilled it’s finally happening. One thing that makes it especially meaningful is that my sister Ann is flying in from Tucson to see the show. She’s never seen me perform it live, and it means the world to me that she’ll be there.
I haven’t been to Chicago since the pandemic, so I plan to walk around, stop at favorite haunts, and catch up with friends. I’m also coming in a day early to appear on WGN-TV for an interview and to sing a song. Sadly, I’ll be rehearsing while the Pope is at Rate Field—a lot is happening in Chicago on June 14!
ET: “To Steve With Love” began as a live 2022 concert at 54 Below in New York City, received a Grammy nomination and you are now playing in major venues all over the country. How special is it to know that following the uncertainty of pandemic you were able to tap into Sondheim’s extraordinary catalog and create such an enduring experience for audiences everywhere?
LC: It’s incredibly special. I never dreamt this show would have the life it has. In 2022, I was originally scheduled to do a movie music show at 54 Below, but after Sondheim passed away, I decided what I really wanted to do was pay tribute to him—to sing his songs and share stories for people who were missing him, like I was.
I did four nights, and afterward, a lot of people urged me to record a live album of the show. It hadn’t crossed my mind, but I realized it would be nice to capture the moment. So, I put on my record producer hat, added two more shows, recorded them live, and released the album in November 2022. The next year, it was nominated for a Grammy—something I never expected.
To share Sondheim’s incredible songs in concert—and to know this album will live on for future generations—is something I’ll always treasure.
ET: This project is as much your story as it is a celebration of Stephen Sondheim—a beautifully curated journey of your experiences together. Talk a little about the process of selecting the songs and how the live show has matured over time?
LC: When I decided to create this show, I started by making a list of stories I might tell, important moments in my career, and all the songs I might want to sing. I also jotted down phrases and lyrics that came to mind: “I was younger then”… “I was there”… “Forty years ago.” The most challenging part was finding an opening number. I went back to my list of phrases and lyrics, and realized it needed to be a medley and include the song “Someone in a Tree.”
The more I’ve performed the show, the more the songs have become a part of me. At first, I was nervous—so many lyrics! It took so much concentration. It still does, but now I feel a greater sense of ease. And over time, I’ve honed my stories. In the beginning I rambled quite a bit. Dad would be proud.
ET: It’s not lost on anyone who knows the special relationship that you and your sister Ann Hampton Callaway have with your dad, John Callaway, that your Chicago concert at the Studebaker Theater on June 14 is during Father’s Day weekend or that you have paid a special, and very touching tribute, to John on the album. John was a longtime personal friend, mentor, and a beloved broadcaster in Chicago for over fifty years. So, whenever you and Ann perform together in your various concerts, it feels like a family reunion for everyone in the audience on many levels.
What influence did your parents have on developing you and Ann’s unique, but very complimentary styles, and how have you managed to work so seamlessly with Ann while both of you maintained long-term—and extraordinarily successful—careers across the entertainment industry?
LC: Our parents exposed us to all kinds of music growing up—jazz, classical, Broadway, pop—and they encouraged us to explore our own tastes, which ended up being very different! We always say that the one album that united us as kids was Carole King’s Tapestry.
Though Ann and I have had wonderful, diverse solo careers, we cherish every chance we get to perform together. Singing with my sister is my greatest joy.
ET: Suppose you are conducting one of your masterclasses or speaking to a talented newcomer who wants to dive into the Sondheim catalog. What is a short list you could offer as a starting point… key resources, people to watch, and listen to, and a few pieces to build confidence or, perhaps, a few to save for later down the road?
LC: Great question. There are some wonderful interviews available on YouTube—Steve’s conversation with Adam Guettel is a favorite, as is Inside the Actors Studio (which I appeared on along with my Merrily We Roll Along castmate Jim Walton). There’s also a terrific Substack newsletter called The Sondheim Hub, which features excellent interviews and deep dives into his catalog. Highly recommend.
I would suggest listening to cast albums. Hearing Pamela Myers sing “Another Hundred People” on the Company cast album when I was a kid had a huge influence on how I sing.
I think it’s also important to choose age-appropriate songs. One of the benefits of getting older is that I can now sing—and truly understand—the incredible material Steve wrote for older women. But there are so many great songs for younger performers to start with: “What More Do I Need?”, “I Remember,” and “Anyone Can Whistle,” to name a few. I’d save “Being Alive” and “Losing My Mind” for down the road.
ET: “To Steve With Love: Liz Callaway Celebrates Sondheim” is your eighth solo album. What’s up next? Perhaps another collaboration with Ann and your son, Nicholas, who shares a featured duet on this one?
LC: I’m working on a new album and heading into the recording studio this summer to record a number of songs. A duet or two is a strong possibility!
PHOTO: Michael Hull
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