How Casting Directors Duncan Stewart and Benton Whitley Cast Broadway's Chicago | Playbill

Special Features How Casting Directors Duncan Stewart and Benton Whitley Cast Broadway's Chicago The musical's longtime casting directors explain the art of finding big name celebrities to take on the revival.
Duncan Stewart and Benton Whitley Luke Fontana

Duncan Stewart has been casting Chicago the Musical on Broadway for over 15 years. His business partner, Benton Whitley, has been casting the musical for 10 years. Is it difficult to maintain such a well-known property?
“Hell yes, it’s hard!” Stewart chuckles. “All caps!”

That’s partially because Chicago has become something of a revolving door for celebrities. A sample of the stars that have graced Chicago’s stages in its 23 years on Broadway: Academy Award winner Cuba Gooding Jr., Emmy-nominated actor Sofía Vergara, Grammy winner Brandy Norwood, telenovela star Jaime Camil, NFL running back Eddie George, and country stars Jennifer Nettles and Billy Ray Cyrus. The list goes on. It’s a strategy created by Chicago producers Barry and Fran Weissler.

“Some people call it stunt casting,” says Stewart. “We firmly call it star casting.”

The pair run the Stewart/Whitley casting offices in New York City, where they cast for TV and film, the 2019 Tony Award–winning Hadestown, Rock of Ages, and the recent Broadway productions of Natasha, Pierre & The Great Comet of 1812, On the Town, and Pippin.

Contrary to popular assumptions, Chicago is not an open door for any A-lister to come play. Three or four times a year, the casting directors create a list of hundreds of names for potential celebrities. Then they decide—with the producers, creatives, and marketing team—which stars they want to audition.

“From that, maybe you get eight people in a year who express interest, who we audition and see a tape on,” says Stewart. “And maybe two or three end up getting cast during the year.”

Suffice to say, Stewart and Whitley constantly cast Chicago. (They also cast the national tour and have worked on star casting for the recent West End production.) The long-running musical may be more work than your average Broadway show, but they feel the rewards as they watch actors transform into bona fide eight-shows-a-week performers.

“On a yearly basis, we get the true honor of giving a handful of people their Broadway debut,” says Whitley, “It’s part of passing on this deep, rich tradition of musical theatre and Broadway. It never gets old.”

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