All the Nude That’s Fit to … Bill Keller, Heather Graham Almost Collide at Sotheby’s Big Naked Auction Night

Maria Esposito came to Wednesday night’s 18th Annual Take Home a Nude silent charity auction at Sotheby’s with five girlfriends, one of them a serious art collector who thought the others would like it if they gave it a try. Ms. Esposito had never been to an art auction before; the only advice her collector friend gave her before sending her out into the galleries was, “If you find something you love, go for it.”

Ms. Esposito, who said with a sheepish giggle that she works as a mortgage lender, was looking at Lot 126, Melissa Andersen’s In Love, a pair of tiny canvases that together depicted a naked woman lying with her back toward the viewer. “It kind of made me sad, but it’s beautiful,” Ms. Esposito said. She wrote in a bid of $450.

Another person who really liked that picture was the actress Heather Graham. 

“That one stuck in my mind the most,” Ms. Graham said. “I thought it was kind of beautiful and sexy.”

Wearing a tight black strapless dress with black heels and a peace sign around her neck, Ms. Graham was standing now in front of a different painting, a big colorful abstraction by Ross Bleckner that had been donated by the Mary Boone Gallery. Ms. Graham’s friend and business manager Carrie Malcolm had really fallen for it, and was hovering in its vicinity in order to protect it from other bidders. Ms. Graham was there to cheer her on.

“She’s my supporter,” Ms. Malcolm said, with appreciation. “We’re in it together.”

But Ms. Graham was in her own world, thinking with longing about In Love, which hung from a wall on the opposite end of the auction floor. She glanced in its direction occasionally, and it was easy to see now that she regretted not putting down a bid. “I’m new to fine art, so I’m a little bit shy,” she said sadly.

Just then Ms. Graham noticed that the Bleckner painting her friend was after had caught someone else’s attention.  

“You’ve been outbidded!” Ms. Graham exclaimed. Ms. Malcolm went over to check. The pot stood at $1,900, and the auction wouldn’t be ending for at least another 20 minutes. “I have been!” Ms. Malcolm said in dismay, and contemplated bidding again right away versus waiting until there was less time on the clock.

“I’m going to wait,” she said, after a time. “I mean, I don’t know. It’s so hard to figure out how to win at an auction.”

This was too much for Ms. Graham, who evidently was still thinking about In Love.

“O.K., now you’re making me want to go look at the ones I liked!” she said, and the pair made off into the crowd with some urgency.

The silent auction would continue until 8:30 or so, at which point the evening’s really big prizes, those painted by superstars, would be sold live in a separate room by a gavel-wielding Sotheby’s professional. Among the works offered at that time: a life-size white puppy by Jeff Koons, and a 30″ x 22″ custom portrait—”your face here”—by William Cotton. Also: a watercolor of a family by Eric Fischl, a charcoal drawing by Jenny Saville and a new acrylic by Kenny Scharf.

For all that star power, though, it was really the first part of the evening—basically a busy cocktail party, complete with mini-burgers and honeysuckle martinis—that felt like the evening’s main event. First-timers like Ms. Esposito mixed with conspicuously seasoned collectors; fashion people like Kate Spade and Evan Yurman; and artists dressed in silly costumes. The event honored John Currin, who with his wife-muse Rachel Feinstein often appears in the pages of Vogue. The actress Elizabeth Berkley was also present.

The photographers Paul Solberg and Christian Makos, known collectively as “The Hilton Brothers,” strolled around looking at art, saying hello, and encouraging double takes with their eye-catching garments. Mr. Makos, the older of the two, wore a dark suit with bright yellow, green and red horizontal stripes. Mr. Solberg, with his spiky hair, kind of  resembled the lead singer of Sugar Ray, except with Buddy Holly glasses and an unfashionable red tie.

“That guy’s trying to compete with me, isn’t he,” said Mr. Makos, gesturing with a restrained snarl toward the investor and philanthropist Ludwig Kuttner, who was dressed in a suit that was comically broad in the shoulders.

Mr. Solberg had a photograph in the auction—a 36″ x 60″ print showing a metallic-looking, in-your-face Jesus Christ.

“It’s a very suggestive photograph remarking on today’s obsession with sex and religion,” Mr. Solberg explained. “You know, today, currently. Like the obsession with David Letterman. And the obsession with Don’t Ask Don’t Tell.”

A reaction to current events, in other words. Almost like journalism!

What did Bill Keller, the executive editor of The New York Times, think of Mr. Solberg’s photograph? “I’m not an art critic,” Mr. Keller said as he walked by the work. 

According to Eric Fischl, Mr. Keller is not alone. Which is to say, Mr. Fischl doesn’t think anyone’s an art critic these days. Surrounded by admirers in the main corridor adjacent to the auction hall, Mr. Fischl argued that contemporary art scholarship has ceased to exist.

“Partly it’s because there’s so much fucking contemporary art, and it goes so fast,” Mr. Fischl said. “Who can stop and think about it?”

“I’ll give you a lesson,” he went on. “When pluralism happened in the late ’70s, early ’80s—when the hegemony of modernism really broke down … The institutions that were bringing the art to the public, which was museums and galleries and stuff, couldn’t keep up with covering it all. So what happened was, the only place where you could keep up with the rapid change was in the media. That’s when the real criticism went away. And the people who are critics now are just guns for hire who write catalogs that go to promote an artist’s career.”

One thing that some people at the party knew and many didn’t was that this ostensibly silent auction would include an unadvertised “phase two,” during which an auctioneer would come around to all the lots in the hall, one by one, and conduct a mini-auction for each of them. Bidding would start where it left off during phase one, the idea being that the people who submitted bids in writing would gather around the work when its turn came and fight for it in the flesh. 

It was a strategically choreographed surprise twist—one that the auctioneer, a fellow named Matthew Cooleen, who used to work in the structured credit trading group at Deutsche Bank and who now runs his own fund, said gets the Academy of Art an average of a 20 percent bump on each sale. Mr. Cooleen explained that catching people off guard was part of the method. 

“Most silent auctions you effectively just take everything down and say, ‘We’re done,'” he said. “People would body block each other to put down their last bids.” His way, he explained, was all about putting energy into the room. “We try to create an event,” he said. “We try to create a party atmosphere. What happens is at the beginning a lot of people don’t understand what we’re doing—they think they’re at a regular write-in auction. And after a while they’re like, ‘What’s going on over there?’ And they finally catch on and it becomes a tsunami, with everyone wanting to see the action.” Plus, he said, people have fun when they’re bidding each other up face to face. “This is New York City. People like to get in there and scrap it up a little bit.” 

One person who wasn’t into this surprise thing at all was Liev Schreiber. “It’s not fair,” he said. “It’s really not fair.”

Later, the actor drew applause when he won Mr. Fischl’s watercolor in the live auction for $52,000.

All the Nude That’s Fit to … Bill Keller, Heather Graham Almost Collide at Sotheby’s Big Naked Auction Night