Every Celebrity Who's Been in Chicago the Musical: Photos

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Ariana Madix

"To say this is a fulfillment of a lifelong dream would be an understatement," Ariana Madix told PEOPLE during a Chicago press call at 48 Lounge in New York City just before she debuted as Roxie Hart in January 2024. "This is quite literally everything to me. It's all I've ever wanted. And to be here now, having this full-circle moment ... I feel so beyond grateful."

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Keltie Knight

Emmy Award-winning host Keltie Knight made her "Broadway debut" as Roxie Hart with the cast of Chicago during CBS' 2023 coverage of the Thanksgiving Day Parade.

"Twenty-three years ago as a young dancer, I moved to New York City with the dream of being on Broadway. With a deep respect and passion for theatre, I unsuccessfully auditioned for over 30 shows," said Knight. "Even though I eventually danced with the Rockettes and as a backup dancer for artists like Taylor Swift and Beyoncé, I have always held onto my dream to make it to a Broadway stage one day. After transitioning to hosting television, it is fitting that I'm singing and dancing in Roxie's shoes as a member of the press! I'm thrilled to bring some extra razzle dazzle to our wonderful viewers Thanksgiving morning."

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Olivia Holt

The actress and singer, 25, made her Broadway debut in Chicago on April 10, 2023, at the Ambassador Theatre.

In photos of her curtain call, Holt was seen sporting Hart's signature blonde curls, a bright red lip and a black one-piece. Her 8-week run in the award-winning revival wraps up on June 4.

"I am incredibly honored to play the iconic role of Roxie Hart. And I'm tremendously grateful to the Chicago company and Broadway community as I've admired their work and work ethic for years," Holt told PEOPLE in a statement. "Theater is where I fell in love with performing and this has been a dream of mine since I was a kid. I feel so lucky to be joining this extraordinary production."

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Angelica Ross

The Pose and American Horror Story actress made her debut on the Great White Way last September as leading lady Roxie Hart for an eight-week engagement, according to the show's official social media.

Ross' casting made her the latest openly transgender woman to star in a Broadway production, joining stars like Kate Bornstein (Straight White Men), L Morgan Lee (A Strange Loop), Alexandra Billings (Wicked) and Peppermint (Head Over Heels).

"Chicago's Roxie Hart is one of the most recognizable, iconic and beloved characters in the history of Broadway, and a true talent like Angelica Ross will delight audiences with her impressive acting, singing and performance skills," GLAAD Vice President of Communications & Talent Anthony Allen Ramos said in a statement provided to PEOPLE.

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Pamela Anderson

"I'm like a sponge. I'm just soaking it all in," Anderson told PEOPLE of her April 2022 debut on Broadway as Roxie Hart. "Every single experience has been just wild. I mean, it's wild to even be here. I have to pinch myself sometimes because it seems so surreal."

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Wayne Brady

Famous Celebs - Chicago the Musical — Len Prince

Actor, comedian, and singer Wayne Brady (Whose Line Is It Anyway?) had his first Broadway credit in 2004 with Chicago, playing Billy Flynn. He's since starred in multiple Broadway shows including Kinky Boots and Freestyle Love Supreme.

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Brandy

R&B superstar Brandy played Roxie Hart to much acclaim in 2015.

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Christie Brinkley

Supermodel Christie Brinkley had three separate runs in Chicago — all as Roxie — in April 2011, April 2012, and April 2019.

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Mel B

Spice Girl Mel B spiced up Chicago in 2016.

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Kandi Burruss

Grammy winner, Real Housewives of Atlanta star, and Broadway vet! Kandi Burruss stepped into the role of Matron "Mama" Morton in 2018.

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Jaime Camil

In 2016, Jane the Virgin star Jaime Camil came to Broadway, as Billy Flynn.

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Lynda Carter

The original Wonder Woman played Matron "Mama" Morton in 2005.

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Maxwell Caulfield

Cool Rider and Broadway star! Grease 2 lead Maxwell Caulfield played Billy Flynn in 2007.

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Billy Ray Cyrus

"We want Billy" — Billy Ray Cyrus, that is! The country singer stepped into the role of Billy Flynn back in 2012.

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Charlotte d'Amboise

Two time Tony nominee Charlotte d'Amboise has starred as Roxie Hart a few times on Broadway over the years. The actress, who had a memorable arc on One Life to Live in 2009, last played the role in January 2020, months before the coronavirus pandemic shuttered Broadway.

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Paige Davis

Before becoming a household name in Trading Spaces, Paige Davis trod the boards on Broadway. So it only made sense that in 2004, she'd return to Broadway as Roxie Hart.

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Kara DioGuardi

American Idol judge and singer/songwriter Kara DioGuardi played Roxie Hart in 2011.

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Sandy Duncan

Longtime Broadway fave and The Hogan Family star Sandy Duncan was Roxie Hart in 1999.

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Eddie George

NFL star and Heisman Trophy winner Eddie George scored a touchdown on Broadway, playing Billy Flynn in 2016.

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Erika Girardi

Real Housewives of Beverly Hills star Erika Jayne's run as Roxie Hart in 2020 was cut short by the Broadway shutdown during the height of the COVID-19 pandemic.

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Cuba Gooding Jr.

Oscar winner Cuba Gooding Jr. played Billy Flynn on Broadway twice, in 2012 and 2019.

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Joel Grey

Oscar winner Joel Grey originated the role of Amos Hart in the Chicago revival.

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Melanie Griffith

Melanie Griffith led Chicago as Roxie Hart in 2003.

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George Hamilton

Screen star George Hamilton made his Broadway debut as Billy Flynn in 2001, and later reprised the role in 2002 and 2007.

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Michael C. Hall

In 2002, Dexter and Six Feet Under star Michael C. Hall played Billy Flynn.

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Todrick Hall

YouTube superstar Todrick Hall brought his triple-threat talents to Chicago in 2018, playing Billy Flynn.

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Melora Hardin

Before tearing up the ballroom on Dancing with the Stars, The Office alumna Melora Hardin was Roxie Hart in 2008.

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Samantha Harris

Roxie Hart was also played by former Dancing with the Stars co-host Samantha Harris, in 2009.

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Marilu Henner

Taxi star Marilu Henner had a memorable turn as Roxie Hart in 1997.

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Jennifer Holliday

Speaking of Tonys, Jennifer Holliday — a Tony winner for her unforgettable role in Dreamgirls — played Matron "Mama" Morton in 2001.

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Carly Hughes

American Housewife star and Broadway vet Carly Hughes was Velma in 2015.

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NeNe Leakes

Matron "Mama" Morton got a dose of reality when Real Housewives of Atlanta breakout NeNe Leakes played her in 2015.

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Huey Lewis

Chicago brought Huey Lewis his Broadway debut, too. The singer/songwriter — known for songs like "Hip to Be Square," "The Heart of Rock & Roll," and "I Want a New Drug" — played Billy Flynn in 2007.

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Marcia Lewis

The late Marcia Lewis originated Matron "Mama" Morton in the Chicago revival, getting nominated for a Tony in the process.

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John O'Hurley

Seinfeld actor and Dancing with the Stars champ John O'Hurley was Billy Flynn in 2006.

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Vincent Pastore

Just over the bridge from New Jersey, where Vincent Pastore found fame as a star on The Sopranos, the actor played Amos Hart in Chicago, joining the cast alongside his costar Aida Turturro in 2007.

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Bianca Marroquin

Bianca Marroquin played Chita Rivera in the acclaimed miniseries Fosse/Verdon, charting Rivera's experience in one episode working with Bob Fosse on Broadway's original Chicago run. In a great example of art imitating life, Marroquin has also starred on stage in Chicago's Broadway revival over the years, as both Velma Kelly and Roxie Hart.

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Brian McKnight

Grammy-nominated singer and producer Brian McKnight made his Broadway debut when he played hotshot lawyer Billy Flynn in 2007.

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Gretchen Mol

Boardwalk Empire star Gretchen Mol also made her Broadway debut in Chicago, as Roxie Hart back in 2004.

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James Naughton

The first Billy Flynn in Broadway's Chicago revival was Gossip Girl actor James Naughton, who won his second Tony for the role.

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Jennifer Nettles

Country superstar Jennifer Nettles made her Broadway debut as Roxie Hart in 2015. She's since gone on to star in Waitress, and release an album of showtunes covers.

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Bebe Neuwirth

Cheers actress Bebe Neuwirth won a Tony Award for her portrayal of Velma Kelly in the 1996 revival. She's since returned to the production multiple times over the years, playing Roxie Hart and, most recently, Matron "Mama" Morton.

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Ann Reinking

Late actress Ann Reinking starred in the original production of Chicago back in 1997, and reprised her role as Roxie Hart when the revival opened on Broadway in 1996. She also choreographed the production, winning a Tony Award in the process.

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Kevin Richardson

Backstreet to Broadway! Backstreet Boys singer Kevin Richardson was Billy Flynn in 2003.

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Lisa Rinna and Harry Hamlin

Before The Real Housewives of Beverly Hills, actress and soap star Lisa Rinna played Roxie Hart alongside her husband Harry Hamlin (as Billy Flynn) in 2007.

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Chita Rivera

The late Chita Rivera originated the role of Velma Kelly in the 1975 production of Chicago on Broadway. And 25 years later, she returned, this time as Roxie Hart — playing the part in Toronto, Las Vegas, and London.

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Roz Ryan

Broadway star and longtime voiceover actress Roz Ryan has often played Matron "Mama" Morton on the Great White Way over the years. She first debuted in the production in 2006, and most recently starred it in it 2016.

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