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David Letterman is a drag. Ask Jean Moss. Long before the Late Night star flew the NBC coop for CBS, she shot him for the cover of Esquire. As she tells it, the 1986 encounter was a cross between Stupid Pet Tricks and a day in the dentist’s chair.

“He’s tremendously self-conscious,” says Moss, whose people skills and sharp eye have led her to a successful career shooting magazine covers, advertisements and film posters. “He won’t take direction. I’d say, `Sit up’ and he’d hike his shoulders to his ears. He needed to be in control. But you have to yield a little to the photographer.”

While Letterman did his best to sabotage the shoot, Moss practiced a little subterfuge of her own. “Children, celebritites, especially in his case, and animals-they’re uncontrollable. So you just keep shooting. You shoot way too much fun-must be a Freudian slip-way too much film,” she corrected herself, “and hope for the best.”

While Herb Ritts works body-conscious California and Annie Leibovitz snaps the vain and famous in New York, Moss picks plum assignments coast to coast, photographing everyone from Walter Cronkite to Spuds MacKenzie.

She does babies, too. But don’t liken Moss to the wannabe rocker playing bar mitzvahs. She’s the queen of Chicago’s commercial photography world and the babies she photographs are Gerber models.

A photographer’s photographer-smart, straightforward and professional-she’s hung with Michael Jordan (shooting him for a McDonald’s ad, Nike and Sports Illustrated) and hit it off with John Goodman (whom she photographed for a poster promoting last summer’s “The Babe”). And when she’s not shooting athletes and actors, Moss manages a corporate roster that includes Sony, Helena Rubinstein and Dewar’s White Label.

An easy-going gabber-the type who treats a stranger as an old friend-Moss makes one think of those old-fashioned, finger-flip picture books, offering a steady (if choppy) stream of anecdotes and observations. In a field populated by divas (on both sides of the camera), she’s delightfully down-to-earth, discussing her work with a kind of wide-eyed wonder, as if she can’t quite believe how she makes her living. Although she’s been in business for more than 10 years, she still finds each photo session “deliciously uncomfortable.”

Whether working in her cavernous South Michigan Avenue studio, a corner office on Wall Street or a Hollywood backlot, every time is the first time. “There’s always a certain pain when you’re shooting,” she says. “I mean, it’s not like manufacturing widgets. You don’t know what you’re going to end up with. A lot of times, you’re just waiting for something to happen. It’s a very uncomfortable feeling, but it’s a wonderful feeling.”

The `M’ factor

This uncertainty stems from Moss never knowing how her subjects will react. “Models love to be in front of the camera. Movie stars hate it. They need to know their `motivation.’ That’s a joke.

“A photograph is all a matter of energy, shape, design. It’s about the way you hold your hand, or the way you sit. It’s about eccentricity. It isn’t about motivation.”

Nonetheless, the “M” factor is unavoidable when shooting posters for such movies as “Dad,” “Curley Sue” and “Lost in Yonkers” (which hits theaters in May).

“If Richard Dreyfuss says to me, `What’s my motivation?’ I get in trouble telling him to be the character. Because a movie poster isn’t about the character, it’s about the celebrity in the character.”

As one might imagine, shooting stars can be stressful. After all, they’ve got producers by their balance sheets and the money men bend over backward to make the big names happy. Moss is expected to do the same. Putting people at ease is part of her business; sometimes that includes “babysitting” egos.

A lot of cooks in the kitchen

Shooting the “Used People” film poster in Toronto was another story. “That was a wonderful job. Shirley MacLaine, Jessica Tandy, Kathy Bates and Marcia Gay Harden are all funny, intelligent people. Shirley MacLaine ran around saying, `Oh! You’ve got to get a shot of this,’ or `Let’s do our fish faces!’ It was just hysterical.”

Romantic icon Marcello Mastroianni had suggestions, too. As Moss notes, “He was such a loverboy in all his movies. So I went in thinking of him with his jacket slung over his shoulder. But when I proposed that type of pose, he said, `That’s how you see me from another era. I’m older now. It isn’t appropriate.’ He was right.”

Raised in Uptown, Moss now makes her home on the North Shore with her husband, a commodities trader, and 12-year-old daughter. Although she spends her days dealing with the big boys at Leo Burnett and Universal, it’s not hard to imagine her roaming the mall with her daughter-and forgetting where she parked the car.

Chatting in her studio against a wall chock-a-block with some of her portraits (Ralph Lauren, Woody Allen, Willie Nelson, Clint Black, William Hurt, John Updike, David Mamet), Moss laughingly recalls her inauspicious beginnings. “I’d had a little training at the University of Wisconsin (at Madison), but I was basically self-taught. When I started out, I just had some shots of dancers from the theater department. I had longtime exposures from the Baha’i Temple, the most gross, idiotic stuff you’d ever seen.”

So how does she account for her success? “I can’t speak for my clients, but I think they like the fact that I’m concept-oriented. When I shoot a CEO, I’m doing a professional portrait. It’s not for Spy magazine.

“When I do a movie poster it’s a photo logo, a sales tool. I understand advertising. I know the casting has to be real, but idealized. I know style, I know it’s not store-bought. Even in advertising, there has to be a certain truth.”

A few kind words

“What I like best about Jean,” says Bob Wyatt, a Leo Burnett art director, “is her intense enthusiasm. There isn’t a minute when she isn’t excited about what we’re doing. She really keeps the creative juices flowing.”

Mark Stevens, an associate creative director at Tatham Euro RSCG, a Chicago ad agency, is quick to credit Moss for her “outstanding homework.” The two have collaborated on a number of celebrity-centered campaigns, including one with John Madden for Ramada Inn and another with Terri Garr for Yoplait Yogurt. “Jean leaves nothing to chance,” notes Stevens, “which is really important when you’re dealing with a celebrity and you may only have 10 minutes to get the shot.”

One of her first assignments was shooting toilet valves for a plumbing manufacturer. One of her more recent images-for Nike-shows Bo Jackson barely contained in an old, clawfoot bathtub. Although Moss claims to know zip about sports, she has tackled a number of assignments with athletes.

What about free tickets?

“I know nothing about sports. But that’s OK because a lot of sports figures don’t want to talk sports anyway. They’d rather talk about clothes, good books, movies, a great restaurant.

“When I photographed Scottie Pippen for the out-of-the-shadow-of-Michael-Jordan shot in Sports Illustrated (Feb. 4, 1992 issue), I told him that the women at the magazine thought he was so good-looking and a great dresser. So even though I only had him for 10 minutes, I asked him for a shot in street clothes. He went and changed.

“Why? Because he was into it. He likes nice shirts and good shoes.”

One of her more recognizable photos is the Spike and Mike shot (Lee and Jordan, that is) for Nike. “It was the first time they had worked together and they were very excited. That made it easy for me, easier than if I had had to shoot either one of them alone. It was like that when I did John McEnroe and his wife (Tatum O’Neal). Much easier than shooting him by himself. But it was a big event for me, because Spike Lee and Michael Jordan are two major people who have such a great social influence on children in this country.”

Touche

With a spread for Money magazine out of the way, Moss turns her attention to yet another session. “I’ve got (White Sox stars) Robin Ventura and Ozzie Guillen coming in this week (mid-February), so I’m using my assistants as stand-ins working up a few poses. That way, we’ll have a place to start. But chances are, when those guys get here, it’s not going to work. Because they’re not my assistants. So, we’ll have to start all over.

“It’s times like these when I want to say, `Wait a minute! I spent three hours working on this. I know that if you stand like this, it will look wonderful.’ “

No matter who the subject-famous entertainer or anonymous executive-Moss is out to show people at their best. “I romance a face. I romance power or talent. It’s like fashion photography. Everybody’s rolling around in the alley, but that alley is fabulously romantic.”