Photo Diary: Olivia Holt Takes Us Backstage of Chicago on Broadway

Since its debut in 1975, the musical Chicago has been a beloved mainstay on Broadway—it currently holds the title for the longest active-running production—and the stylish shoes of its infamous murderess Roxie Hart have been filled by a slew of noteworthy names. Originally portrayed onstage by Gwen Verdon, the role has since been played by the likes of Liza Minnelli, Renée Zellweger (in the 2002 Oscar-winning film adaptation), Michelle Williams, Ashlee Simpson, Christie Brinkley, Pamela Anderson, and Angelica Ross, to name a few. 

Taking up the torch in its current run is actress and singer Olivia Holt. The 25-year-old, who starred in last year’s hit series Cruel Summer, kicked off her eight-week engagement at the Ambassador Theatre on April 10, taking on favorite musical numbers "Funny Honey” and "Roxie.” The performance marks Holt’s Broadway debut and a thrilling one at that. So before the curtain falls on her final June 4 show, we asked the actress to document a typical day in the life playing one of the most iconic stage characters.

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(Image credit: Olivia Holt)

"I start the day with a walk and a yummy oat milk latte that I usually end up taking to go to the theatre.”

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(Image credit: Olivia Holt)

"I start my skin prep using Shani Darden’s Weightless Oil-Free Moisturizer ($48) and serum and Sonya Dakar’s Blue Butterfly Balm ($85).”

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(Image credit: Olivia Holt)

"Then I go in with some light foundation using Koh Gen Do foundation and Nars concealer and fill in my brows with Anastasia Beverly Hills Brow Wiz Ultra-Slim Precision Brow Pencil ($25) in Taupe. I begin my smoky eye with Makeup by Mario Master Mattes Eyeshadow Palette ($50) and Dusty Rose Blush ($30).”

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(Image credit: Olivia Holt)

"Our wonderful hairdresser Barry getting me wig ready!”

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(Image credit: Olivia Holt)

"Roxie’s little black wardrobe.”

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(Image credit: Olivia Holt )

"Along with some fun shoes…”

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(Image credit: Olivia Holt )

"A quick warm-up and stretch before I get dressed for act one.”

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(Image credit: Olivia Holt )

"It’s officially showtime!”

Catch Olivia Hart in Chicago on Broadway from now until June 4. 

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Executive Director, Entertainment

Jessica Baker is Who What Wear’s Executive Director, Entertainment, where she ideates, books, writes, and edits celebrity and entertainment features.