Celebrities who hit big – and didn’t – in ‘Chicago’ on Broadway

The musical “Chicago” has a bad history of guessing who will be the next word on everyone’s lips.
Whether it’s Melanie Griffith, Brooke Shields, Pamela Anderson, Christie Brinkley, Ariana Madix or Usher, producers Fran and Barry Weissler have long accepted hiring untested stars who have never been on Broadway, but who have no experience with theater at all.
Can they sing? Can they dance? They can sell?
The risky couple’s strategy has paid off — more than once — turning John Kander and Fred Ebb’s 1970s musical revival about the Windy City killers into Broadway’s longest-running show and the second-longest of all time behind “The Phantom of the Opera.” It’s an $800 million machine.
Every time “Chicago” starts to sink and the sharks smell blood, a famous face comes in.
So, who gave the box office the old razzle dazzle and who gave it the fizzle fizzle?
The Weisslers’ latest gamble is Whitney Leavitt.
Far from Lea Michele or Idina Menzel, Leavitt, 32, is the star of “The Secret Lives of Mormon Wives,” a Hulu reality TV show, and a contestant on “Dancing with the Stars” Season 34. She came in 6th place.
But he is in first place in this race. Earlier this month, Leavitt propelled the 29-year-old production — almost as old as he is — to its highest-grossing week ever with ticket sales of $1.4 million.
An assistant at the Ambassador Theater who had never heard of him until now said to the cheers of the fans, “It’s like Yankee Stadium in here!”
Leavitt’s run has been extended through May 3.
The first major celebrity to prove the “Chicago” stunt casting model could really work was “Working Girl” herself.
In 2003, when the musical was seven years old and had already been adapted into a 2002 Oscar-winning film starring Renée Zellweger and Catherine Zeta-Jones, Melanie Griffith was cast to play Roxie Hart.
Why does a movie star with no stage debut take on the role of a disgruntled musician who shoots and kills his lover and claims self-defense with the help of his brilliant lawyer Billy Flynn?
Griffith was in trouble at work, and his life had become a gossip. But ex-husband Antonio Banderas was seen across the street from “Nine,” and the commitment period was less than three months.
The practice wasn’t easy, The Post’s Michael Riedel reports. Music producer and original Roxie, Ann Reinking, had to arrange Bob Fosse’s dance moves for her. And one time Griffith wanted to delay his first day a week.
But one day before he was due to start, he performed for an audience of three – Banderas, Chita Rivera and Barry Weissler – and had the courage to continue.
Clive Barnes’ Post review headline read: “Melanie can’t sing, dance or act, but she’s a star.” All those who criticized him loved him.
That’s the key. Griffith set an important precedent for future bold-faced Roxies: To be great, you don’t have to be a triple threat. Don’t even be a threat that doesn’t exist. Just be yourself.
The actress showed a great drawing, and everyone agreed it was Roxie. Griffith sold more than $1 million in tickets before his first night, and played to sold-out houses the rest of his run.
Who should come next? And why stop at Roxie?
Other well-known screen actors followed, although the traditional thespians turned out to be less fruitful pools of money.
There was Brooke Shields, fresh off the sitcom “Suddenly Susan,” who made her London debut as Roxie.
While singing at the pool in 2005, Tom Cruise, who was 42 at the time, went on the “Today” show and attacked his way of fighting depression, which he talked about openly in his book “Down Came the Rain: My Journey Through Postpartum Depression.” Cruise, being a Scientologist, called Shields “useless.”
They both reached for the gun. He shot back Cruise, who was dating 26-year-old Katie Holmes at the time, and said, “If he wants to see ‘Chicago,’ I left him two tickets — one adult, one child.”
The West End loved this play.
When Shields transferred it to Broadway that September, he didn’t do Griffith’s numbers. The actress was not so surprised as she had appeared in the song “Grease,” “Cabaret” and “Wonderful City.” But he increased the house to 90% capacity in some of his time.
Drama is clearly a painting. So, in 2006, the beloved rom-com actress and wife of Tom Hanks Rita Wilson was not the most faithful Roxie. Her gross was $450,000 a week — credited with the show of the decade 20 years ago, but part of the business of “Mamma Mia!” he did it. Still, the audience cheered him on.
Not true for model and Billy Joel’s ex-wife Christie Brinkley, who took over Roxie in 2011 at age 57. Fans online raved about his performance. And the Daily News wrote that “there was a sign of blankness because of Brinkley’s empty description.” Oh well. “Uptown Girl” sold enough tickets that she was asked to return in 2019, at the age of 65.
The latest movie star to fail to wow the audience or the cash registers was Mira Sorvino last fall.
Word of mouth was bad for the “Romy and Michelle’s High School Reunion” star, and some weeks the Oscar winner played up to 68% capacity – not what you want in a well-known business.
That’s much better, however, than Miss USA Tara Conner, who has the unique distinction of selling $0 tickets.
In 2007, the Weisslers were secretly rehearsing Conner as Roxie at a studio in Chelsea.
Like some of his predecessors, Conner had fallen into disgrace. Three months after being crowned in 2006, he was caught drinking and snorting cocaine in a nightclub in New York. To avoid losing his title, the owner of the event Donald Trump sent him to reform.
Then, straight to dance class!
“They have been pressuring him to see if he is ready for that,” said the source at the time.
“If both sides are free, this will be a win for all parties,” Barry told The Post after the news broke. “We look forward to making the wonderful announcement about him joining the ‘Chicago’ family.”
They did not make an announcement. Conner was released two weeks later.
Perhaps no one has seen a sharper change in career after dancing the “Hot Honey Rag,” however, than “Baywatch” actress and Playboy Playmate Pamela Anderson.
At 54, she began a two-month run as Roxie in April 2022, igniting the media while Broadway was still limping after COVID.
I was there when she premiered, and I said in my review, “Pam could have been Ethel Merman considering the roar.”
That week’s freshman enthusiasm was up nearly $300K to $829K. However, no one realized that this was the beginning of the second game of showbiz.
Three years later, Anderson received her first Golden Globe nomination for the epic film “The Last Showgirl,” and co-starred with Liam Neeson in the popular “Naked Gun” reboot. This spring, his new film, “Rosebush Pruning,” premiered at the prestigious Berlin Film Festival.
But we can’t let the girls be happy.
Between Griffith and a recent string of successful TV stars, several of “Chicago’s” hires were male—Usher.
The R&B star, then 27, played Billy Flynn in the summer of 2006 — and hundreds of fans flocked to 49th Street to watch the legendary singer step out of a convertible at the stage door. Costs rose, too, to over $800,000 a week.
When he caught a sore throat and had to sit out his last eight games, the take dropped by $400,000.
“We hope Usher gets well soon,” Barry told The Post at the time. “He was one of the best Billy Flynns we ever had.”
Could that be because the show grossed an estimated $1.7 million in seven weeks?
Oscar winner Cuba Gooding Jr. he also played Billy in 2018. Unlike Usher, ticket buyers say he’s one of the worst Flynns they’ve ever seen.
Meh. During its run, “Chicago” still outsold “Kinky Boots,” “School of Rock” and “Beauty: The Carole King Musical.”
But for the country singer and Miley’s father Billy Ray Cyrus, the work broke his heart, his broken, broken heart. Ambassador sat at about 65% sold while singing “All I Care About Is Love.”
In recent years this show has been heavily charged with a dose of truth.
The top three cash cows of “Chicago” were, in fact, regulars of the unscripted series, who, like Leavitt, brought strange, bad fans to Broadway.
Jinx Monsoon, winner of Season 13 of “RuPaul’s Drag Race,” broke a box office record in 2023 playing Matron Mama Morton.
And Ariana Madix of “Vanderpump Rules” gave the show its highest non-holiday week in 2024 as Roxie.
“Chicago” would run another three decades on Bravo alone.
The revival of “Chicago” will celebrate 30 years in November, in large part due to the shoving of stars on the stage – good, bad or not to be underestimated.
This well-known actress is very popular as last time she was shown for the first time in Season 3 of HBO’s “The Comeback,” starring Lisa Kudrow as the actress who washed Valerie Cherish.
When the unprepared Valerie walks into Roxie’s room, it’s a much bigger challenge than she expected.
“Maybe I should have seen the show before I said, ‘Yes’,” she told her husband. “The music never ends, song by song.
That’s “Chicago”!



