Annie Leibovitz: Intimidating and not. She talks about her new photo book ‘Wonderland,’ what celebrities are like and how magazines are less glossy.

Years ago I had a dream that I worked for Annie Leibovitz and she hated me, so she made me work on Thanksgiving and then she fired me because the alligator that I personally wrangled for Nicole Kidman to ride in a photograph for the next issue of Vanity Fair, the poor creature looked tired. I’m not joking about that dream. I think I had just read a biography of Rolling Stone founder Jann Wenner and Leibovitz and her legend and herself factor hugely. She very much gave that magazine its look, and later became synonymous with outsized, crazily theatrical celebrity portraiture. That alligator thing, you can imagine it, right? Besides, when you’re Leibovitz, once you’ve suspended Ben Stiller in a bubble above the Seine, dressed Beyonce as Alice in Wonderland and arranged Lena Dunham inside a window display on a busy street — all actual pictures she created, two of those included in her new book, “Wonderland” — what is a dream?

One of the best stories about Leibovitz is that time she photographed Queen Elizabeth II (also in the book) and asked Her Majesty to remove the crown. The Queen was sort of, well … Wait, who are you? The problem, Leibovitz told me, was a BBC crew was filming this and made it look as if the Queen stormed out when actually she stormed in.

Alright, I thought, either way, sounds like a dream.

Leibovitz was in town the other day for a Chicago Humanities Festival event. Before it began, we met at her hotel in River North, and though I am not supposed to admit this, I was weirdly nervous. So much so, I felt my lips quiver. Which never happens. In fact, I once rode in a cab with Nicole Kidman, and she was so pleasant, I never once perspired, but Leibovitz, she has a reputation as controlling, pitiless, steamrolling. She had already asked not to be photographed for this story, then changed plans and times before agreeing. Nervous, I blurted out my dream about her — the firing, alligator, etc.

She replied, deadpan, “Sounds about right.”

Turns out, Annie Leibovitz is a lot of fun to talk to, generous, pensive, candid, with a sense of humor about her military-operation-like Condé Nast shoots of the famous — as well as steamrolling and controlling. She began talking about “Wonderland” (Phaidon Press, 2021) without a prompt or even a question, and about 10 minutes passed before I got a single word in.

And it was fine.

Not to say this is the kind of celebrity back rub that might accompany her own celebrity spreads, and not that you want the subject of a story to dictate the terms, but she took charge with an air of benign efficiency, with a journalist’s jittery grasp of time, conversation and pace. She likes to keep things moving. She’s known for working nonstop and at 72, after conversation drifted to the pandemic, she noted, “I am still working nonstop.” But she also took pains to note, she only had a brief period — during the Nixon years, with Hunter S. Thompson — when she considered herself a journalist.

“I’ve been doing this 50 years now. Rolling Stone, where I started — and I was getting assignments pretty much right away — was more photojournalistic, but I also realized I couldn’t be a journalist because I liked having a point of view. So then I started doing portraits. … Listen, (photojournalism) is incredible right now. The most incredible I have seen in my life. It is knocking (expletive) socks off. The work is astounding, and if I was a young photographer, I’d want to be a journalist today. I thought of myself that way for like five minutes, but I got into this because of Robert Frank and Henri Cartier-Bresson, and they were more like surrealists. So my work became more like personal reportage.”

She looked down, lost in thought.

Then, as if reminding herself why she was there, she brought it back to fashion and “Wonderland,” which, at least in conception, is a book of fashion photography, heavy with images she made for Vogue. “It’s a departure,” she said with the briefest of cringes.

She discusses her two-plus decades of fashion work with a mix of pride, appreciation and self-consciousness. “OK, maybe it’s not a departure. It was fashion work I didn’t know what to do with. Fashion, I have been doing since I did a Kate Moss couture shoot for Anna Wintour in 1999 or so. I thought it was ridiculous! Frivolous! Very low man on the totem pole stuff. Then I began to appreciate designers as artists. So look, the whole narrative to this book is I am not a fashion photographer. I went kicking and screaming into this book: Eghhh! I don’t know … COVID happened and I started thinking about it.”

She speaks in bursts of insight, which break into fragments, thoughts that dead end only to circle back a moment later, sometimes resolving, sometimes left dangling. She will say, with a low chuckle, something like “That reminds of something Mick Jagger once told me,” before noticing herself name-dropping and then never saying what Jagger said.

“The reality is,” she went on, “this is all playfully over the top. And look, no one likes having their picture taken. They feel like they are at the dentist. And then suddenly, oh my God, you find you’re photographing people who want to be photographed!” Indeed, despite what she says, the book is full of people who appear to go to great lengths to be photographed. It’s centered on images inspired by “Alice in Wonderland” and “The Wizard of Oz.” Keira Knightley is Dorothy. Designer Tom Ford plays the White Rabbit.

That sort of thing.

Nevertheless, the real world intrudes.

Books aside, Leibovitz works in magazines, of course, which have not seemed much of a growth industry these days. Like other print media, each monthly issue of Vogue, once a thick reminder of the reach of advertising, has seemed closer to a pamphlet lately. “So no, (magazines) do not have the money now to do these same kind of shoots,” she said. “They don’t have that money now, and they shouldn’t. I don’t feel like it’s that time anymore. The work I did at times, some of those (photo shoots) were like small films. And that’s not appropriate now. Still, I actually like the way I’m working now. I am given less money (for a shoot) — not that I am not going to pay for a shoot myself — and then every few years I go off on my own to finish a book. Like ‘Pilgrimage’ (2004), which is locations, and no people.” Images of the leafy path where Darwin paced daily. The snow swept Ohio plains of Annie Oakley’s youth. “It’s like cement between the bricks for me.”

Even with “Wonderland,” Leibovitz couldn’t resist slipping in current events.

“I kept adding politics and I had to say, stop already. I used that Trump picture” — taken in 2006 on an airport tarmac, Melania in a gold bikini, quite pregnant, Donald, seated in a car, quite obscured — “but that’s a true fashion picture. It was for the ‘Shape’ issue of Vogue. Even the Tammy Duckworth picture is a fashion story, too. I had to use that.”

Photographed by Leibovitz in 2018, Sen. Duckworth is in her Washington office, three-year-old daughter beneath her desk, another then-infant daughter pressed against her.

“We show up, a Vogue editor is there with three or four things on a rack for her and Tammy tells me, she has suits on a rack and she shows me and says she buys St. John Knits suits through eBay. So, OK, we have to do an eBay suit! So that’s what she’s wearing. More and more people do this now. Because the covers of Vogue are not just fashion models but people, they get a say now, they know how they want to look, and what they want to wear — which is what they should have been doing anyway. I love that. I mean, I could do a whole other book on the loss of the portrait, where you get people who are dressed for pictures. That’s been painful. No, I have a long standing agreement with Anna that I can photograph people in their own clothes. But some do like the (magazine’s) clothes. The first time I photographed Venus and Serena Williams, I wanted to do power pictures of their bodies. They were so upset. It was Vogue! They wanted to get dressed up! Michelle Obama, she was the first lady I photographed who insisted on dressing in what she wanted to wear. It was a big deal for her to wear something like J. Crew, something anyone could wear it. Which was a long way from Nancy Reagan in Oscar de la Renta. The Queen, first and second time, (her staff) give you catalogs and say, OK what do you want her to wear? You’re picking the earrings, and so on. I originally asked if I could photograph her riding her horse at Windsor and they came back, ‘No horse, no Windsor, just Buckingham Palace.’ So I decided I would do something more formal. I had a half hour. I literally layered her, the dress, the cape, then of course, there was that controversy about the crown. I asked her to take it off.”

I suspect the room dropped a few degrees, I said.

“It’s complicated. She was flustered to begin with. Then settled down and didn’t leave until I said, ‘Thank you very much.’ I loved her. Feisty! But politics things, can be, oh …”

She picked up her cellphone, held it before me, then put it back on the table.

And went on talking.

Wait, I said, stunned, did you take my picture?

“You don’t stop seeing pictures,” she said.

After all, as she reminded me later, she is, at heart, a portrait photographer. The word “iconic” is so misunderstood and overused that it’s virtually meaningless now, yet it’s not overstating things to describe Leibovitz’s best-known images as iconic portraits of the 20th century. Soldiers rolling up the White House carpet as Nixon helicopters away in disgrace. Demi Moore nude and pregnant for the cover of Vanity Fair. John Lennon, nude and curled around Yoko Ono. Many others, as familiar as they have become, remain merely wonderful — Steve Martin, in a black and white paint-splattered suit, poised before a matching Franz Kline painting; Keith Richards on tour, completely out.

She’s shot everyone.

Her memoirs — she’s considered writing one, but remains uncertain — could be as densely stuffed with incident and celebrity as Andy Warhol’s diaries. Of touring with the Rolling Stones, Leibovitz once wrote that she thought she could become a chameleon, become such a part of the background that she would be forgotten, and in the end, no: “I did everything you’re supposed to do when you go on tour with the Rolling Stones.”

Decades later, she thinks of her portrait work as expansive — reportorial, conceptual, essayistic. She doesn’t have to admire her subjects. She remembers the time she shot Woody Allen in his home as “creepy”; she mentions photographing Harvey Weinstein with his mother and says, “I’m not sure that picture makes sense anymore.” The Oz in her “Wonderland,” the creep behind the curtain, was painter Chuck Close, who later faced allegations of sexual harassment; he died last year at 81. The image was made in 2005. She was aware then of the issues surrounding him, she said, and sees the image now as a kind of artifact from “a period of time. Though to be clear, I did not like him.”

She’d rather like the people she photographs. “It’s my Achille’s heel. I like to like them. That’s not supposed to be a part of this. That’s when it gets into being judgmental. When you can say, ‘OK, I’m doing journalism now.’ I don’t know … It’s hard to explain. You are in the moment, and usually, proud to be taking that picture in that moment.”

When it came time to take her picture for this story, she said to the photographer, “I don’t see myself. I need your direction. Some see themselves. I don’t. I don’t like having my picture taken.” She noted her suitcase, erupting clothing. “You could do ‘Life on the road …’” He pointed her instead to a corner of her hotel room and brushed hair out of her face. She said she would now be “simulating relaxation.” She said she hated the room.

I suggested a more Leibovitz-esque image. Perhaps dangling her outside the window?

“Yeah, yeah, exactly,” she said, then, to the photographer: “I look cranky. I always look cranky. It’s the way I look! Don’t take it personally!” After a few minutes, less time than it took Leibovitz to shoot the Queen of England, she stood: “OK … It’s good … I’m like a piece of food — I’m fine. I mean, normally I’m a terror on these things, but no, I’m fine.”