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Novelist Marcus Sakey has been probing the dark side of Chicago since 2007, having published five crime thrillers including Good People, which is currently being developed into a film starring Tobey Maguire, reportedly.

For his latest project, Sakey broadened his scope. As the writer and host of the new Travel Channel series Hidden City, Sakey travels America to investigate some of the nation’s most iconic true crime stories. The author visits 12 metropolises and explores the more notorious corners of their pasts—the tales which reveal a city’s true character, he says.

The debut episode airs Tuesday, Dec. 6 at 9 p.m. CST, and features three of Chicago’s defining dramas: the reign of terror of serial killer H.H. Holmes, the rise and fall of John Dillinger, and the violent culture clash of the 1968 Democratic National Convention riots. The A.V. Club talked to Sakey, freshly returned from taping in Alaska, about how he uncovers Hidden City’s stories, the unique joy of getting pepper-sprayed, and fashion tips for interviewing porn stars.

Sakey tells www.avclub.com – I also got to interview a porn star in L.A. about the Wonderland murders. This was one night with a drug deal gone wrong, murder, retributions, and John Holmes, the porn star, was involved.

One of the people I got to interview was Bob Chinn, who Burt Reynolds’s character in Boogie Nights is based on. But we wanted to talk to a modern porn star, so I met with a woman named Kayden Kross. She was great. She was so articulate and thoughtful and fully aware of the psychodynamics of what it was she was doing. It was a fascinating interview.

The funny thing is, it was awkward and uncomfortable for me—not at all because of her, but because of trying to figure out what you wear to go talk to a porn star. I’m staring at my closet thinking, “Would that look like I’m hitting on her? I don’t know…”