ANNA AND DAVE: Anna Wintour exposed her funny bone during her taping of “The Late Show With David Letterman” Monday afternoon, appearing as a guest on the program to discuss “The September Issue” and promote the citywide retail event Fashion’s Night Out on Sept. 10. But even before Wintour stepped out in front of the studio audience (which included, for support, publisher Tom Florio and contributing editor William Norwich), Letterman was already working hard to warm up the oft-proclaimed “ice queen.”

“They say that she’s aloof, bitchy and mean to her staff,” Letterman joked during his monologue. “Oh, wait, that’s what they say about me.” He also said he was wearing a “Vera Wang hairpiece” in honor of the Vogue editor in chief.

This story first appeared in the August 25, 2009 issue of WWD. Subscribe Today.

As he introduced her, Letterman plunked a copy of the September issue of Vogue on his desk — that is, the September 2007 issue featured in the movie, not the current one with Charlize Theron on the cover.

Wintour, clad in a black-and-white Carolina Herrera dress, poked fun at herself, walking out in her trademark sunglasses but then removing them for the interview. She also played along with most of Letterman’s jokes. When Wintour described the scene from “The September Issue” that was to be excerpted during the program, Letterman said, “I heard it was a car crash and an explosion.” To which Wintour said, “That’d probably be better.” When Letterman asked if young people also worked at Vogue, after noting the magazine seemed to be run by editors his age, Wintour said: “Vogue is not only run by senior citizens.”

And later, when the talk show host said he was surprised at how certain parts of the magazine are still undecided within a week of close, Wintour said, “You do it, too — you only called me on Friday.” (That is, for the pre-interview, not for the actual booking.)

Letterman admitted he’d never been to a fashion show, but said they look like they are occupied by “beautiful women who look like the Neptunians have released them. But nobody buys that stuff, do they? Is somebody walking around like they’re from Neptune?”

“Lots of people,” Wintour snapped back, laughing.

She even dished out fashion advice. Wintour complimented Letterman on his “interesting” socks, and recommended he look into Thom Browne since the designer’s short-length suits show off fancy footwear. Asked if someone only has $20 in their fashion budget, what should they buy to still be fashionable, Wintour replied to audience laughter: “Well, you could buy lipstick.”

Nor did Wintour speed off in her Town Car immediately after her segment — she stayed to watch New York Yankees first baseman Mark Teixeira hit fastballs down 53rd Street while a few hundred Times Square tourists looked on. Letterman joked the Vogue editor “can throw a mean cutter,” but — unsurprisingly — she neither pitched nor swung a bat. — Stephanie D. Smith

RDA FILES: Reader’s Digest Association filed for bankruptcy protection on Monday. Under a prearranged plan with lenders, RDA’s debt will be slashed to $550 million from $2.2 billion. Last week, the company said more than 80 percent of its senior financial lenders were on board. RDA’s lender group, led by J.P. Morgan Chase & Co., has committed $150 million in new financing that will come into play during the reorganization and beyond. The company said it expects to operate “business as usual,” publishing all of its titles and digital offerings.

RDA’s filing only applies to its U.S. business and the company expects the process to be concluded expediently. “Our business operations remain solid, with anticipated fiscal 2009 revenue only down by low single digits, currency neutral, despite the recession,” said chief executive officer Mary Berner. — Amy Wicks

THE RUMBLES ROLL ON: Cintra Wilson’s controversial review of J.C. Penney, which ran in The New York Times on Aug. 13, remained a hot-button issue for readers on Monday. They were ignited once again by a column that ran Sunday, from public editor Clark Hoyt. “I guess this woman forgot that The New York Times is read by people outside New York, even in (God forbid) Indiana, where I am,” said one commenter. “I am neither obese nor (I hope) dowdy, but I found her piece just plain rude and mean-spirited.”

“The lesson, I think, is that it is OK to have fun with your readers,” wrote Hoyt. “It is not OK to make fun of them.” He also spoke to executive editor Bill Keller, who told Hoyt he wished the piece had never been published. It “would make a fine exhibit for someone making the case that The Times has an arrogant streak,” Keller added, noting the column will be a teachable moment. Trip Gabriel, editor of the Styles section where the review ran, was quoted by Hoyt as saying Wilson’s column often is more social critic and her columns are only to a secondary degree service journalism. That differs from what a Times spokeswoman told WWD the day the column ran: “The Critical Shopper column has always had an edge and a point of view — it is supposed to review, after all.” — A.W.

SELFLESS GLAMOUR: Reader reaction to women’s magazines was once confined to tightly edited letters pages and salon chatter, but as editors trained on slick, packaged editorial plunge into the messy worlds of blogging and tweeting, they’re increasingly explaining themselves in whole new ways — with mixed results.

Take the issue of body image and representation, virtually guaranteed to drive traffic and spur heated reactions. Earlier this month, Self editor Lucy Danziger was forced to defend her magazine against charges that it had radically altered its September cover shot of Kelly Clarkson to make her look thinner.

Blogs like Jezebel compared the cover photo with readily available candids and a behind-the-scenes video on Self’s own Web site, and the story was kept alive on multiple blogs and social networks. Danziger duly dove in, writing in her blog on Aug. 10: “Did we alter her appearance? Only to make her look her personal best. Did we publish an act of fiction? No. Not unless you think all photos are that. But in the sense that Kelly is the picture of confidence, and she truly is, then I think this photo is the truest we have ever put out there on the newsstand.”

Few Internet correspondents were satisfied, arguing it was hypocritical for a fitness magazine to simultaneously extol one’s “personal best” while artificially shrinking its cover model. Four days later, Danziger was on the “Today” show, where host Meredith Vieira and model Emme were both deeply skeptical of the editor’s explanation, with Vieira telling Danziger she was “sending two different messages.”

The following week, on Aug. 17, Glamour editor in chief Cindi Leive — who used to edit Self — blogged about a photo from her September issue that she said had been generating enthusiastic feedback from readers: a nearly nude, size 12 to 14 model with a little bit of a belly. “The e-mails were filled with such joy — joy at seeing a woman’s body with all the curves and quirks and rolls found in nature,” she wrote.

Leive didn’t mention the Self controversy, but she didn’t have to — several commenters made the connection for her. “Meanwhile, at Self magazine they are ‘editing’ Kelly Clarkson on their cover, after Kelly had just said she felt comfortable in her own skin…Thanks for being real, Glamour!!” wrote one.

The post soon generated a flood of positive comments and pickup (though some bloggers urged their readers not to get too excited at a single photo), racking up 386,000 unique visitors, almost 50,000 of them referred through Facebook, according to a spokeswoman. On Monday, Leive had her own body image segment on “Today,” where she regularly comments on women’s lifestyle issues, and the lead-in referred to a “recent backlash” against Self for its September cover. (Leive herself didn’t mention Self.)

When Leive was asked if the reaction to the curvier model was going to change anything in women’s magazines, she replied: “Speaking for my own magazine, I think it absolutely will….You get a reaction like this, and you can really see it. It’s also a sign of the times that women are really looking for a little bit more authenticity and a little bit less artifice in every part of their lives.” A CNN appearance followed.

Danziger is on vacation, but a spokeswoman said, “Self routinely shows healthy women’s bodies of all shapes and sizes. We also get positive feedback on these inspiring models every month and often publish these letters in the magazine. Self believes the more discussion about positive body image, the better.” — Irin Carmon