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Callaway Comes Home and Chicago Heats Up
Summer is in full swing
Happy Friday!
After a much-needed staycation downtown last week with my pal Noelle, I can safely say Chicago is in the swing of summer. Many, many thanks to the lovely team at the Four Seasons Chicago for making a friends’ weekend so dreamy (more on that in a forthcoming article).
The streets are alive with tours, the Mag Mile is a veritable salmon stream, and even Universal Studios’ Epic Universe is moved in right next to the Apple store on the river. It does a heart good to see so many people loving this magnificent city.
I hope you have something fun planned for the weekend!
Until Next Time,
Amanda
Callaway Comes Home

Photo Courtesy of Gustavo Ernestine
The melodies of The Swan Princess drifted in and out of my mind. Lying on the carpet in the living room of my childhood home, I was enraptured by Odette. But it wasn’t her story that got me, it was the music. Her soaring voice and turn of phrase had me parroting her repertoire in easy counterstep to my obsession with The Lion King.
Fast forward a few years. There was something ever-so-familiar about Anastasia’s singing voice. A transcendental quality that had me waltzing around the living room with my sister, forever in love with “Once Upon a December”—an infatuation that remains to this day. That cassette tape got so much play time that my player eventually wore it out. The following year, the same fondness occurred when The Lion King II: Simba’s Pride was released.
Time and time again, Liz Callaway became the soundtrack of my childhood.
In the same way that Nathan Lane and Robin Williams inspired my love of plays, Callaway sparked my penchant for musical theater. Even if two-year-old Amanda didn’t know it yet. There was something inescapable about her voice and all of the lives it could portray. So, when the opportunity came to see her perform a one-night-only engagement in Chicago, there was no way I could miss it.
To Steve With Love: Liz Callaway Celebrates Sondheim was a love letter to the maestro himself. It was clear from the start how deeply she admired not just Sondheim as a theater professional, but as a person. Stuffed with his music along with anecdotes about their work together, Callaway dazzled in the magnificent Studebaker Theater last Saturday night. Her tribute had been performed in many parts of the world, but never in Chicago, never in her hometown.
There was something particularly moving about being in that historic theater, full of stage aficionados, humming with the tunes of Sondheim. Every one of us clutching to their love of the man and his work for our own reasons. When Callaway said sometimes it’s hard to remember he’s gone, a soft murmur of agreement wafted through the space. I couldn’t shake the emotion of a performer I’d long admired speaking of the work that inspired her to do what she does, knowing that she is a very similar figure in my life.
Callaway’s one-woman show is a celebration of Sondheim, sure. It’s also more than that. It’s a celebration of the inherent power of music and how it can bring people together in countless ways. A theater full of people who, in vastly different circumstances, have been impacted by Callaway’s artistry and/or Sondheim’s unsinkable melodies. It’s a celebration of that feeling you get as the instruments swell into “Send In the Clowns” or the nostalgia that comes from “Broadway Baby.”
So, while the evening was supposed to be about Sondheim, I was grateful for the chance to celebrate Callaway. Although little Amanda didn’t know Sondheim or his work, those animated film soundtracks she did know got her through a lot. Nowadays, when I need a get-it-out song, I still turn to Callaway. “I Want It All” from Baby is one of my go-tos. Heck, I even had a song from Baby as a processional in my wedding.
You never know where an artist’s work will take you.
I guess “far longer than forever, as constant as a star…” was more than just a lyric for this musical kid.

Noelle, Liz Callaway, and I
Chicago A&E News
About Face Theatre’s OM Mission follows Zahra and Shanta as they uncover the previously unsung histories of Black lesbian Blues women from the 1920s and 30s. What starts as a search in silent archives transforms into a vibrant, joyful tribute that celebrates these historical figures and inspires a more inclusive future for Black lesbians today. Originally commissioned by About Face, this 80-minute show runs at The Den Theatre from June 20-28.
About Face Theatre presents Dionne Addai's Life Out Loud: Voices of Pride. This is a charming, funny, and interactive play where three friends explore an LGBTQ+ history gallery, uncovering surprising stories and new perspectives on gender and sexuality. The 60-minute production uses monologues and improv to teach about gender-inclusive vocabulary, coping mechanisms, and boundary setting. Catch one of the two remaining special performances this summer through the Night Out in the Parks program.
Hell in a Handbag Productions is hosting a series of five staged readings for LGBTQIA+ Pride Month at The Clutch, located at 4335 N. Western Ave. The series begins with The Chain on Friday, June 20 at 7:30 pm, followed by Death of a Cheerleader on Saturday, June 21 at 7:30 pm. Joan Crawford Goes to Hell will have two performances on Friday, June 27 & Saturday, June 28 at 7:30 pm. The series continues with The Gnadiges Fraulein on Saturday, July 5 at 7:30 pm, concluding with Anna and the Wig Monster on Sunday, July 13 at 3 pm.
Steppenwolf Theatre presents global drag icon Sasha Velour! She is bringing her new theatrical spectacular, The Big Reveal Live Show, to Chicago's Steppenwolf Theatre for three performances only from August 1 – 3, 2025. The 90-minute show, following sold-out engagements in the U.S. and Europe, will feature high-concept lip syncs, artful oration, and comedic segments. Tickets range from $47 to $107.
Windy City Smokeout is kicking off this year's festival with a pop-up featuring Katz's Delicatessen at Bub City in River North on July 9 from 11 a.m. to 3 p.m. For $45 per person, attendees can enjoy Katz's Pastrami Sandwich, sides, and live country music, plus a chance to win festival passes. Tickets must be purchased in advance via OpenTable.
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