Jacket, from a selection, Chanel. Satin blouse, Anne Klein
($295); bloomingdales.com; trousers, 3.1 Phillip Lim ($550); shoes, from a selection, Christian Louboutin

Claire Simon has that light-up-a-room aura. But it’s her business to spot that aura in other people. As the president and director of Chicago’s most high-profile casting agency, Simon Casting, she has recently placed local actors in roles in Gwyneth Paltrow’s Contagion, the new Superman flick out in 2013, Man of Steel, and Kelsey Grammer’s series, Boss.

The scope of her work is staggering: In late February, Simon begins casting 83 roles for the second season of Boss, which starts filming in Chicago in March and which earned two Golden Globe nods for Best TV Drama Series and Best Actor in a TV Drama. It’s a huge process done with only seven days to prep and cast an episode. “We get the script the first day, cast it on the second and third days, and then get network and studio approvals, book, and send the cast to wardrobe,” she explains.

Simon, who began her casting career in 1996, says she connects with actors on a visceral level. She started out as one, and spent 10 years pursuing an acting career, until one day after an “inspirational” Oprah Winfrey Show segment she asked God to give her a sign—should she continue acting or give it up? Two weeks later she was pregnant. “I thought, Whoa, that wasn’t the sign I was expecting,” she says. “I thought He would throw Steven Spielberg my way.”

Raising her young daughter, she decided she needed to have a “stapler, a tape dispenser, and a desk” and soon landed a position at Aria Talent, where she spent five years. “I loved taking care of actors. It was so much easier to promote someone whom you really believe in.”

And the rest was history, Chicago-style. Ever since she founded her own agency almost 15 years ago, she’s had a hand in a dizzying collection of film, television, and theater projects, including Chicago-made movies like High Fidelity, Hardball, and Save the Last Dance. For the small screen she’s casted shows such as The Chicago Code, Detroit 1-8-7, and Prison Break, for which she won an Artios Award for Outstanding Achievement in Casting. Simon Casting also works on about 25 theater projects a year, including Million Dollar Quartet at the Apollo Theater Chicago and Show Boat at the Lyric Opera of Chicago. According to Reel Chicago, Simon has landed more TV-series jobs for Chicago actors than any other casting agent in town.

“My job is to know the talent in Chicago so that when a film comes here and they give me the script, I can find the [actors] they want,” says Simon. “It’s like painting a beautiful picture with people.”

When asked about the favorite movie she’s worked on, she says, “It would have to be Hardball with Keanu Reeves. We had to find real kids—not actors—from the inner city to play the leads, and we searched all summer and found five of the seven leads in Chicago.” She smiles at the memory. “A few of the kids have had to the opportunity to go to college because of the money they made.”

Simon, joined by her tight-knit staff of six, is all about the process. “My goal is to listen to the director’s vision, whittle down the options, and present the best of Chicago,” she says.

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