"If you grew up around here, the legend of Al Capone is like a bed time story you read to little kids," Moore said. "I think the gangland lore of Chicago, it's based in the sidewalks here, it's part of the pavement."
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Leonard is a master tailor in Chicago in the 50s, with scathing secrets. Gangsters use his shop as a "front" - and that's based in truth.
"The first bug the FBI ever planted, they planted to get at the mob, and they planted it in Chicago in 1956 inside a tailor shop," Moore said.
"The Outfit" is Moore's directorial debut.
"Oh yeah, handing someone this stack of paper and saying, 'Hey, I think this script could be made into a great film, could you make it for me because I don't know how?'" Moore said. "It seemed instead that no, the responsible thing to do was to learn how to make it myself."
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Moore's script for "The Imitation Game" won an Oscar. He took his mom, Susan Sher, who was Michelle Obama's chief of staff, and is a key executive at the University of Chicago.
Graham's speech made headlines.
"When I was 16 I tried to kill myself because I felt weird and I felt different and I felt like I did not belong," he said. "I would like for this moment to be for that kid out there who feels she's weird or she's different or she doesn't fit in anywhere, yes you do."
Later, he reflected: "It's nice to have this gold trophy in my closet that I can look at now and again and remember, well, maybe I am ok at this, and keep at it, I can make more things."