Entertainment Theater Every Celebrity Who's Been in 'Chicago' on Broadway Come on, babe, and take a look at all the many celebrities who have rouged their knees and rolled their stockings down with the cast of the Broadway show (all 57 of them!) By Dave Quinn Dave Quinn Instagram Twitter Dave Quinn is an Editor for PEOPLE, working across a number of verticals including the Entertainment, Lifestyle and News teams. He joined in 2006 as a Writer/Reporter where he became known for his Bravo and Broadway exclusives across print and digital. Dave is the author of the No. 1 New York Times best-selling book, Not All Diamonds and Rosé: The Inside Story of the Real Housewives from the People Who Lived It. He's appeared on many broadcasts including ABC's Good Morning America, Bravo's Watch What Happens Live with Andy Cohen, E!'s Daily Pop, NBC's New York Live and PEOPLE's own Reality Check, as well as a number of podcasts like Bitch Sesh, Everything Iconic, Watch What Crappens, Hot Off the Mess, Mention It All, and PEOPLE Every Day. Prior to working at PEOPLE, Dave was the chief Theater Reporter for NBC New York and co-host of Entertainment Weekly's acclaimed TV Recaps series. People Editorial Guidelines Updated on August 5, 2022 11:00 AM Share Tweet Pin Email Trending Videos 01 of 57 Angelica Ross Angelica Ross. Jon Kopaloff/Getty The Pose and American Horror Story actress is set to make her debut on the Great White Way this September, as leading lady Roxie Hart in Chicago for an eight-week engagement, according to the show's official social media. Ross' casting makes 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. 02 of 57 Pamela Anderson Bruce Glikas/Getty "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." 03 of 57 Wayne Brady 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. 04 of 57 Brandy Jason Bell R&B superstar Brandy played Roxie Hart to much acclaim in 2015. 05 of 57 Christie Brinkley Andrew Eccles Supermodel Christie Brinkley had three separate runs in Chicago — all as Roxie — in April 2011, April 2012, and April 2019. 06 of 57 Mel B Len Prince Spice Girl Mel B spiced up Chicago in 2016. 07 of 57 Kandi Burruss Jeremy Daniel Grammy winner, Real Housewives of Atlanta star, and Broadway vet! Kandi Burruss stepped into the role of Matron "Mama" Morton in 2018. 08 of 57 Jaime Camil Jeremy Daniel In 2016, Jane the Virgin star Jaime Camil came to Broadway, as Billy Flynn. 09 of 57 Lynda Carter Andrew Eccles The original Wonder Woman played Matron "Mama" Morton in 2005. 10 of 57 Maxwell Caulfield Len Prince Cool Rider and Broadway star! Grease 2 lead Maxwell Caulfield played Billy Flynn in 2007. 11 of 57 Billy Ray Cyrus Andrew Eccles "We want Billy" — Billy Ray Cyrus, that is! The country singer stepped into the role of Billy Flynn back in 2012. 12 of 57 Charlotte d'Amboise Jeremy Daniel 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 Jan. 2020, months before the coronavirus pandemic shuttered Broadway. 13 of 57 Paige Davis Len Prince 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. 14 of 57 Kara DioGuardi Josh Lehrer American Idol judge and singer/songwriter Kara DioGuardi played Roxie Hart in 2011. 15 of 57 Sandy Duncan Uli Weber Longtime Broadway fave and The Hogan Family star Sandy Duncan was Roxie Hart in 1999. 16 of 57 Eddie George Jeremy Daniel NFL star and Heisman Trophy winner Eddie George scored a touchdown on Broadway, playing Billy Flynn in 2016. 17 of 57 Erika Girardi Rene Cervantes 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 coronavirus pandemic. 18 of 57 Cuba Gooding Jr. Tristram Kenton Oscar winner Cuba Gooding Jr. played Billy Flynn on Broadway twice, in 2012 and 2019. 19 of 57 Joel Grey Max Vadukul Oscar winner Joel Grey originated the role of Amos Hart in the Chicago revival. 20 of 57 Melanie Griffith Stephanie Pfriender Stylander Melanie Griffith led Chicago as Roxie Hart in 2003. 21 of 57 George Hamilton Andrew Eccles Screen star George Hamilton made his Broadway debut as Billy Flynn in 2001, and later reprised the role in 2002 and 2007. 22 of 57 Michael C. Hall Miranda Penn Turin In 2002, Dexter and Six Feet Under star Michael C. Hall played Billy Flynn. 23 of 57 Todrick Hall Steven & Chad YouTube superstar Todrick Hall brought his triple-threat talents to Chicago in 2018, playing Billy Flynn. 24 of 57 Melora Hardin Joan Marcus Before tearing up the ballroom on Dancing with the Stars, The Office alum Melora Hardin was Roxie Hart in 2008. 25 of 57 Samantha Harris Joan Marcus Roxie Hart was also played by former Dancing with the Stars co-host Samantha Harris, in 2009. 26 of 57 Marilu Henner Max Vadukul Taxi star Marilu Henner had a memorable turn as Roxie Hart in 1997. 27 of 57 Jennifer Holliday Andrew Eccles Speaking of Tonys, Jennifer Holliday — a Tony winner for her unforgettable role in Dreamgirls — played Matron "Mama" Morton in 2001. 28 of 57 Carly Hughes Jeremy Daniel American Housewife star and Broadway vet Carly Hughes was Velma in 2015. 29 of 57 NeNe Leakes Jeremy Daniel Matron "Mama" Morton got a dose of reality when Real Housewives of Atlanta breakout NeNe Leakes played her in 2015. 30 of 57 Huey Lewis Richie Fahey 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. 31 of 57 Marcia Lewis Max Vadukul The late Marcia Lewis originated Matron "Mama" Morton in the Chicago revival, getting nominated for a Tony in the process. 32 of 57 John O'Hurley Richie Fahey Seinfeld actor and Dancing with the Stars champ John O'Hurley was Billy Flynn in 2006. 33 of 57 Vincent Pastore Joan Marcus 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. 34 of 57 Bianca Marroquin Raul Tovar 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. 35 of 57 Brian McKnight Joan Marcus Grammy-nominated singer and producer Brian McKnight made his Broadway debut when he played hotshot lawyer Billy Flynn in 2007. 36 of 57 Gretchen Mol Len Prince Boardwalk Empire star Gretchen Mol also made her Broadway debut in Chicago, as Roxie Hart back in 2004. 37 of 57 James Naughton Max Vadukul The first Billy Flynn in Broadway's Chicago revival was Gossip Girl actor James Naughton, who won his second Tony for the role. 38 of 57 Jennifer Nettles Len Prince 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. 39 of 57 Bebe Neuwirth Max Vadukul 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. 40 of 57 Ann Reinking Max Vadukul 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. 41 of 57 Kevin Richardson Miranda Penn Turin Backstreet to Broadway! Backstreet Boys singer Kevin Richardson was Billy Flynn in 2003. 42 of 57 Lisa Rinna and Harry Hamlin Paul Kolnik 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. 43 of 57 Chita Rivera Uli Weber She 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. 44 of 57 Roz Ryan Jeremy Daniel 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. 45 of 57 John Schneider Amy Arbus Bo on Broadway! Dukes of Hazzard star John Schneider joined Chicago as Billy Flynn in 2008. 46 of 57 Brooke Shields Len Prince Broadway audiences got to see Roxie Hart played by Hollywood icon Brooke Shields back in 2005. 47 of 57 Ashlee Simpson Len Prince "Pieces of Me" singer Ashlee Simpson played Roxie Hart from Nov. 2009 until Feb. 2010. 48 of 57 Valerie Simpson Jeremy Daniel Matron "Mama" Morton was once played by singer Valerie Simpson, of Ashford & Simpson fame. She made her Broadway debut in the production in 2018. 49 of 57 Jerry Springer Len Prince Tabloid talk show host Jerry Springer starred as Billy Flynn in 2007. 50 of 57 Patrick Swayze Bob Frame The late, great actor Patrick Swayze had a brief run in Chicago, playing Billy Flynn in 2003 for a two-week run. 51 of 57 Aida Turturro Joan Marcus Sopranos star Aida Turturro played Matron "Mama" Morton in 2007 alongside her costar, Vincent Pastore. 52 of 57 Sofia Vergara Joan Marcus Sitcom star Sofia Vergara (Modern Family) played Roxie Hart in 2009. 53 of 57 Michelle Williams Uli Weber Destiny's Child singer Michelle Williams joined the cast of Chicago on Broadway in 2010 as Roxie Hart, after playing the role in London. 54 of 57 Wendy Williams Jeremy Daniel Talk show host Wendy Williams made her Broadway debut in 2013 in the role of Matron "Mama" Morton. 55 of 57 Rumer Willis Jeremy Daniel The rumors are true! Rumer Willis did, in fact, star in Broadway's Chicago — as Roxie Hart in 2015. 56 of 57 Chandra Wilson Joan Marcus Grey's Anatomy star Chandra Wilson spent two months in the summer of 2009 treading the boards at Matron "Mama" Morton. 57 of 57 Tom Wopat Paul Kolnik The Dukes of Hazzard star and Tony nominee Tom Wopat was one of the stars who played Billy Flynn in 2008.