Discover how Chicago's bold celebrity casting strategy fuels its record-breaking Broadway run and $800 million success.
- March 31, 2026
AceShowbiz - The musical Chicago has consistently proven itself a master at casting high-profile names to keep audiences intrigued and ticket sales soaring.
Producers Fran and Barry Weissler have embraced a daring approach, often hiring celebrities with little to no Broadway or theatrical background. From movie stars like Melanie Griffith and Brooke Shields to reality TV personalities like Whitney Leavitt and even musical performers such as Usher, the Weisslers bank on star power over traditional theater credentials.
This strategy has largely paid off, helping turn the revival of John Kander and Fred Ebb’s 1970s musical, centered on two Chicago murderesses, into the longest-running show currently on Broadway and the second longest-running overall after The Phantom of the Opera. The production has blossomed into an $800 million enterprise.
Whenever ticket sales begin to dip, the producers respond by injecting fresh celebrity talent to reignite public interest and boost the box office.
So, which celebrities brought the razzle-dazzle to Chicago’s box office and which flopped?
The latest star to take a chance is Whitney Leavitt, known for her role on the Hulu reality series The Secret Lives of Mormon Wives and as a contestant on Season 34 of Dancing with the Stars, where she placed sixth.
Unlike traditional Broadway leads like Lea Michele or Idina Menzel, Leavitt's background is unconventional. Yet, she has made a remarkable impact, driving the nearly three-decade-old production to its highest-grossing week ever with $1.4 million in ticket sales in March.
An usher at the Ambassador Theatre remarked on the energy during her performance, comparing the enthusiastic fans to a crowd at Yankee Stadium. Due to her success, Leavitt’s run has been extended through May 3.
The first major celebrity to validate the Weisslers’ stunt casting gamble was Melanie Griffith. In 2003, seven years after the revival’s debut and shortly after the film adaptation won Oscars, Griffith was cast as Roxie Hart despite lacking stage experience.
At the time, Griffith was in a Hollywood career slump and facing personal challenges, but her then-husband Antonio Banderas was performing nearby in Nine, which reduced the time commitment. Rehearsals were tough, with original Roxie Ann Reinking adapting the choreography for Griffith, who even considered postponing her start.
However, a private performance for Banderas, Chita Rivera, and Barry Weissler boosted her confidence to proceed. Critics responded positively, with The New York Post declaring, “Melanie can’t sing, dance or act, but she’s a star.” Griffith’s casting proved the show’s premise that one need not be a triple-threat to succeed; being authentic was enough.
Her star power translated into massive ticket sales, with over $1 million sold before opening night and standing-room-only audiences throughout her tenure.
Subsequent celebrity castings followed, though not all were as financially fruitful.
Brooke Shields brought star power from television, having recently starred in the sitcom Suddenly Susan. She first portrayed Roxie in London before transferring to Broadway in 2005.
During her London run, Shields was embroiled in public controversy when Tom Cruise criticized her for openly discussing her antidepressant use. Shields responded with pointed remarks, fueling media interest that only added to her allure.
While her Broadway stint did not match Griffith’s record-breaking sales, Shields still managed to boost attendance to about 90% capacity during parts of her engagement.
Other stars, such as Rita Wilson, known for romantic comedies and as Tom Hanks’ wife, joined in 2006 but brought moderate success with weekly grosses around $450,000. Though respectable for a mature show, these numbers paled compared to hit musicals like Mamma Mia!
Christie Brinkley, Billy Joel’s ex-wife and a famed model, stepped into Roxie in 2011 at age 57. Despite harsh criticism and reviews labeling her performance as hollow, Brinkley’s name drew enough fans to warrant a return in 2019, even at age 65.
More recent attempts with established film stars like Mira Sorvino last fall failed to deliver strong box office results. Some weeks saw attendance drop to 68% capacity, a disappointment for a well-known Oscar winner.
Among the most unique cases was Tara Conner, Miss USA 2006, who rehearsed secretly for the Roxie role in 2007 but never officially joined the cast or sold any tickets. Conner’s scandal involving underage drinking and cocaine use led to rehab and ultimately her dismissal from the production before debuting.
One of the sharpest career turnarounds has been that of Pamela Anderson. In April 2022, the former Baywatch star and Playboy Playmate took on Roxie at age 54, generating massive media buzz during Broadway’s COVID recovery period.
Her opening night was met with thunderous applause, and ticket sales surged by nearly $300,000 to $829,000 in her debut week. Anderson’s run marked the beginning of a surprising second act in show business, with accolades and further acting opportunities following.
In summary, the Weisslers’ bold casting choices have been a defining feature of Chicago’s longevity, with some celebrities driving tremendous box office success while others faltered despite their fame. The mix of risk and reward continues to keep this iconic musical vibrant on Broadway nearly 30 years after its revival.