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.
"I start the day with a walk and a yummy oat milk latte that I usually end up taking to go to the theatre.”
"I start my skin prep using Shani Darden’s Weightless Oil-Free Moisturizer ($48) and serum and Sonya Dakar’s Blue Butterfly Balm ($85).”
"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).”
"Our wonderful hairdresser Barry getting me wig ready!”
"Roxie’s little black wardrobe.”
"Along with some fun shoes…”
"A quick warm-up and stretch before I get dressed for act one.”
"It’s officially showtime!”
Catch Olivia Hart in Chicago on Broadway from now until June 4.

Jessica Baker is Who What Wear’s Executive Director, Entertainment, where she ideates, books, writes, and edits celebrity and entertainment features.
-
If You're Going to Wear Brown Leggings, This Is the Sneaker Color to Wear Them With If You Want to Look ElegantA combination meant for only the most elite of workout classes.
-
I Want to Look Chic This Winter Vacation—6 Looks That Nail the BriefWhether you're traveling to Miami, Aspen, or anywhere else.
-
Every Chic Individual Is Wearing "Goth Christmas" Nails Right Now—6 Vampy Sets I'm Currently Obsessing OverElevated, not Ebenezer.
-
PDRN Skincare, Espresso Hair, and Polka-Dot Nails: 9 Trends That Dominated 2025, According to Search DataAs demonstrated by Hailey Bieber, Dua Lipa, and J.Lo.
-
Under-Requested Yet Highly Elegant: I'm Putting Gingerbread Nails at the Top of My Holiday To-Do ListI'm all about this warm, melty, molasses-colored mani.
-
It's Official: '80s Nails Are Back—17 Fashion-Forward Designs Giving This "Dated" Trend New LifeOh, the glamour!
-
Chrome French Manis Are Everywhere—10 Elevated Takes to Text to Your Nail TechWe're already wearing them.
-
Celebs Are Obsessed With Animal-Print Nails—5 Takes That Will Dominate This WinterSnakeskin! Leopard! Tortoiseshell!
-
I'm Desperate to Copy Selena Gomez's Romeo + Juliet Manicure—It's Giving 1996 in the Best WayStar-crossed lovers? More like stunning nail inspo.
-
Kylie Jenner’s Jelly Plaid Nails Prove This OPI Color Is Truly the Most VersatileThe chicest mani staple.