Photo: Sean Williams

Our cover shoot for this week’s issue was quite the production—as you can see. After several traditional modeling agencies turned us down due to the racy subject matter (sex, oh my!), we turned to local performance artist Lady Jack, a.k.a. Lindsey Marks, to be our cover model. She did a beautiful job—and modeling for photos isn’t even her main talent. Lady Jack performs and produces burlesque in Chicago and you can catch her in the act (dancing that is, not in a scandalous back-of-a-cab liaison) in The Wild Party Variety Hour, presented by Silent Theatre Company. The Mary-Arrchie Theatre, 735 W Sheridan Rd, Oct 24 at 10:30pm. Admission is $10.

Which, as it turned out, was pretty much his answer to the first question in our Q&A.

But that was just one impression I had of Hefner when he called from the Playboy Mansion—and, frankly, it’s one he seems to cultivate. As indicated by the following excerpt (not in the published interview), Hefner’s keenly aware of the link between his persona and his product. Yet behind the laid-back, world-at-my-fingertips Hef, he of a rotating cast of platinum-blond girlfriends, there’s also, clearly, a fiercely driven businessman, who, even at age 83, has both hands deep in the workings of his almost-5060-year-old, Chicago-based publication.

Talking with Hefner, one gets the sense that some of his responses come straight off a script he’s thoroughly edited over years of describing himself and his work. Author Steven Watts makes a similar observation in last year’s biography, Mr. Playboy: Hugh Hefner and the American Dream. (Interestingly, the story of self-reinvention that Hefner tells of himself—“There was a moment in time in which I reinvented myself,” he told me. “It was 1959. I came out from behind the desk and started living the life and became, in effect, Mr. Playboy”—sounds pretty similar to the narrative Watts writes.)

Hefner didn’t seem to just read from script, however. The man I spoke to was lively, quick-minded, quick to laugh and—“for the luckiest guy on the planet”—impressively engaged.

An excerpt not in this week’s published Q&A:

TOC: How has sex changed for you?

HH: You have the usual aches and pains you didn’t have when you were younger. When my second marriage failed, I discovered a generation waiting for me to come out and play. The magazine, obviously, like a lot of other magazines, is going through its difficult times, and the company is, too, but the brand is more popular today than at any other time, and part of that has to do with my reemergence.

TOC: You mention the magazine’s troubles. One question asked of Playboy is, can it survive in the age of free digital porn?

HH: I don’t think Playboy and porn have a great deal to do with one another. The brand has continued to be so popular because it’s something more. It is a lifestyle concept that represents personal, political and economic freedom, and it represents that now to both sexes.

TOC: Do you still pick all the Playmates yourself?

HH: Yes, still pick the covers, still pick the Playmates. The home base is still Chicago, but I have contact with my editors every day.

TOC: Do you have an all-time favorite Playmate?

HH: Marilyn Monroe, without question.

TOC: The very first one.

HH: It all began there.

TOC: Do you feel you’ve always been trying to get back to that, or to her?

HH: I wouldn’t say get back to her, but you certainly can see in my own personal tastes that since the end of the marriage I’ve been in very much a blond period, and that hearkens back to the blonds that were popular in the movies when I was growing up. That was obviously epitomized by Marilyn Monroe.

TOC: Is it true you have a plot next to hers?

HH: Absolutely true. The Westwood Cemetery is just a few blocks from my home, and a number of my very dear friends are buried there.

TOC: About ten years ago, you said you’d won the war and the parade after the war and it’s nice to have lived long enough to see that.

HH: Yes, true. George Will walked in at the beginning of an interview and said, “Well, you’ve won.” He was referring obviously to the changing social-sexual values.

TOC: Has sexuality in America changed since then?

HH: I don’t think there’s been a lot of change in the last ten years. The sexual revolution arrived in the middle ’60s, celebrated itself to great excess in the 1970s, and then there was a backlash in the 1980s with the arrival of Reagan in the White House, the Religious Right very much engaged in politics for the first time, the Meese Commission and AIDS. We live in far more liberated times, but the battle goes on. There are still mixed feelings related to images of the nude body.

TOC: Such as?

HH: Well, there is less distribution of Playboy magazine today, and that started in the 1980s with the Meese Commission and the 7-11 stores and threats from the Justice Department and the first references to Playboy in any mainstream way as pornography. And that backlash still impacts distribution and advertising so that there have been instances where an airline stewardess would come up to a reader, male or female, in an airline and tell the reader to put the magazine away, it would offend some people.

Read the published Q&A here.

The masterminds behind this new bling, Chicagoans Tim Gould and Scott Gilbert, say it’s “a ring design developed for the single community to identify themselves the way a wedding band identifies someone as being married.” Okay, guys, seriously, I don’t want to hate on some hometown entrepreneurs who are just trying to launch a business, but I thought the way to identify whether you’re is single is to not wear a ring. The absence of ring.

If a dude’s at a bar, and he notices that minx across the room has a silver band on her ring finger, the making-eyes action is over. He doesn’t think to himself, Say, that sure looks like wedding ring, but maybe I should inspect whether there are interlocking symbols on it that will identify whether she plays for my team and/or is single. No, that guy is on to his next lady prey and MGD 64 in 1.2 seconds.

Gould and Gilbert are counting on the newly divorced or otherwise freshly single people to jump on this bandwagon, eager to show off their available status. But as a divorcee (I love calling myself that, it seems so highfalutin yet scandalous), I can say that the best thing about becoming single again was taking off that ring.

Dude, check out our slide show featuring the cast of Vaudezilla’s Rollin’ Out of Here Naked: A Big Lebowski Burlesque, hitting the Gorilla Tango Theatre stage Saturdays in September. Just don’t spill your Caucasian in your mad scramble to grab tickets.

Tomorrow night (Tuesday, August 11) at 7pm, the Sex Positive Film Series features the film Liberty in Restraint at the Hull-House Museum (800 S Halsted St). According to Early to Bed’s blog (e2b is a community sponsor of the film series), the 2005 film explores Noel Graydon’s journey into the world of bondage, discipline and sadomasochism (BDS&M).  To learn more about this amazing (and did I mention FREE!) documentary film series, visit the Sex Positive Film Series web site or call 312-413-5353 for information or ticketing.

Check out my weekly In&Out sex column in TOC or write to me with your sex questions at in&out@timeoutchicago.com.

Photo: Jimmy Fishbein

New to the whole cover-model scene, late last Monday I was excited but nervous to check out the Time Out cover shoot held at the swanky Dana Hotel. When I found out I was going to be featured in the article, I thought that was enough revenge against a particular ex-boyfriend, but the cover opportunity was just too good to pass up. Armed with my best friend and fellow single Chicagoan (if you want to go on a date, bring a friend and I will too!), we attempted to meet the hair and makeup crew at the psychedelic “Nirvana Suite.” Thank goodness we got too scared by the lack of signage and loud noises coming from behind the door, because when we found a PR lackey to do it for us, it turned out that a little nirvana was being achieved at a Playboy shoot going on in the suite. Just to make sure we “Time Out people” stayed away, they plastered a large sign on the door—guess we didn’t make the cut for that photo shoot.

In the second “Nirvana” suite, I got changed and primped for a “sexy nighttime” look. Charlie, my eligible bachelor co-cover model, got off easy with only a little concealer and powder to cover the aftereffects of a long bachelor-party weekend. After what seemed like eternity (and was long enough that my friend had to leave to make her train), I was led up to the Vertigo Sky Lounge to meet Charlie (who also had the benefit of a few vodka tonics as he waited) and the photographers.

Because of a rain delay, we had to shoot alongside a spirited “cigar party” held weekly at the lounge. Not only did I feel on the spot in my black dress around my new cover-mate, now I had to deal with the leers of 20 or so older gentleman and their monstrous Cubans—not to mention the scantily clad waitstaff in outfits I could only describe as pirate-porn chic.

Photo: Jimmy Fishbein

I was instructed to sit, in what Charlie would dub my “mermaid pose,” on the ledge of a fire pit while he rested comfortably, or as comfortably as one could in a blue suit, on a leather ottoman. Drinks in hand, we were told to gaze into each other’s eyes and pretend to laugh at jokes that we were theoretically telling. This was certainly an unusual first date! Thankfully Charlie, a good-natured (and handsome) redhead, helped make it less awkward as we attempted to communicate through closed mouth smiles and eyelash batting. With each photo and slight adjustment of our rapidly disappearing drinks, the awkward “getting to know you’s” common at the beginning of a date were exchanged. Nothing like a simulated loving gaze to bring two people together.

As the sun set and a rapid change of clothes occurred, it appeared as though our glamorous cover- model days were coming to an end. Back in the suite, we packed up—more like I threw everything into my bag and he carefully made sure not to forget anything (thanks again, Charlie, for reminding me about the expensive designer dress I almost left behind). Walking out the door, we pledged to see each other again, maybe this time not somewhere that would require us to sit awkwardly. Sure enough, on the cab ride home I got a text message asking me out for drinks. Perhaps this Time Out singles’ thing won’t be too bad after all!

Want to date Grace? E-mail her at graceg@tocpersonals.com

But what to do when you have all this amorous capital and nowhere to spend it? That’s where TOC comes in. We’ll help you find that special someone, that perfect companion who looks great on your arm as you sidle up to the Hideout Block Party, rooftop bars, Ravinia and more. And hopefully is a great long-term match—if you’re into that kind of thing.

Here’s how to get in on the TOC love connection: E-mail summerfling@timeoutchicago.com with your name, age, neighborhood, photo (very important!), your match preference (girls or guys) and a few events, concerts, fests, bars, restaurants, etc. you want to hit this August and September. You may appear in an upcoming issue!