So, if Stefano is the new Anna, who will be the Grace Coddington of the film? Will it be Lynn Hirschberg? More importantly, will anyone be the W equivalent of the tennis playing, Louis Vuitton-wearing André Leon Talley?

R.J. Cutler, director of The September Issue, has written a HuffPo column detailing the lessons he learned during his time with the Vogue editor.

Primarily, he learned that she is very powerful:

Her absolute power over a single industry reminded me of Mike Ovitz when he did, in fact, rule Hollywood and all deals seemed to somehow pass through his desk. Or of Frank Rich when he was the Head Drama Critic for the New York Times and his review alone determined a new production's fate -- advance sales, other critical responses and celebrity names on the marquee be damned.

He also learned various managerial pointers--for instance, "Keep Meetings Short," "Trust Your Instincts," "Surround Yourself with Great Talent," and "Don't Look Back."

So what can we learn from R.J. Cutler?

Perhaps that Vogue shenanigans make for highly marketable entertainment. CBS has planned an hour-long special around the 2010 Fashion's Night Out, Wintour's second annual festival of oddly self-righteous shopping.

Says Fashionista:

The program is set to air on September 15, 2010, five days after [FNO] takes place in 13 cities across the globe.

Much like The September Issue, the special will focus on the logistics and creative work that goes into producing something where the end result will (hopefully) make everyone involved a lot of money.

"Hi, Mr. Florio! Can we have a minute of your time for the Observer?" we asked.

He looked up nervously and said, "Oh, no. Are you going to ask me about McKinsey?"

"Um, no?"

"Okay, then."

Mr. Florio told us that his Fashion Week schedule is fairly relaxed and that so far he has been to Max Azria, Thakoon, and Tory Burch. "I try to do a mix of fashion leaders like Oscar as well as newer designers," he said.

If fashion editors attend shows to plan future spreads and retailers to place orders, the Transom wondered, why is someone like Mr. Florio there?

"I look for trends," he said. Like knee-high boots and sculpted shoulders?

He laughed. "No, I look for trends in the business," he said, "Like the whole idea of luxury at a better price point, which is something Tory Burch is doing. I try to get a sense of the sociological trends which our editors will adapt. It just ads a little context. You need to understand the business trends like global warming and fabrics getting lighter and more transitional pieces in fashion. If you can speak intelligently about these things when you sell ad pages, you can sort of take their [advertisers'] point of view."

Interesting! We then asked Mr. Florio what sorts of responses he's gotten to R.J. Cutler's The September Issue, in which he appears a warm and likeable fellow, gallantly defending Ms. Wintour's perceived remoteness.

"The feedback that I have received is that brought back the creativity and hard work of what it means to be in the fashion business," he said. He paused for a moment. "As opposed to those reality shows where these amateurs portray the business as very frivolous."

Did we mention that Elle's Anne Slowey, the star of CW's Stylista, was sitting right across the aisle?

In the last year, Anna Wintour, the typically private Vogue editor, has submitted to a 60 Minutes interview; given a talk at the 92nd Street Y about her charity work; courted White House Social Secretary Desiree Rogers at Monkey Bar and boldly announced at a CFDA town hall meeting that she has friends in the White House. Just last week, Ms. Wintour devoted a few minutes to each reporter who had lined up along the red carpet at the premiere of The September Issue, a documentary by R. J. Cutler about her magazine, smiling and gracefully answering questions.

It is unclear whether Ms. Wintour is trying to soften her image, solidify her legacy or please boss Si Newhouse with this mountain of publicity—or all three—but whatever the reason, it came to an apex last night on CBS's The Late Show, on which she appeared to promote the documentary.

Despite reports that she was strongly advised to leave her sunglasses at home, the Vogue editor entered the stage to Madonna’s  "Vogue" in large black shades, a black-and-white floral, knee-length dress and a heavy necklace of yellow gems. She took the glasses off once she got to her seat. She was wearing heavy blush, dark eye makeup and deep pink lipstick.

“I see you have very interesting socks on,” she told host David Letterman, who wore a suit that was short enough to reveal white socks and black loafers. “There is a designer you should look into called Thom Browne. He cuts pants like really short so you can focus entirely on the socks.”

“Really?” asked Mr. Letterman. Ms. Wintour appeared serious, though Mr. Letterman seemed to think, understandably, that she was toying with him.“Yes,” she replied.

Ms. Wintour sat perched right on the end of her seat, legs crossed and hands neatly clasped. Her tense, forward posture said she was nervous, but for each question Mr. Letterman asked, she replied with quick, prepared answers that were funny and self-deprecating. She laughed at Mr. Letterman’s jokes and she laughed at herself. She laughed even when the comedian’s probing seemed to irk her.

He asked about her reputation. “I read in The New York Times this week that I’m an ice queen, a Sun King, I’m an alien fleeing from District 9 and I’m a dominatrix,” Ms. Wintour said. “So I reckon that makes me lukewarm royalty with a whip from outer space, what do you think?”

“Good gig!” Mr. Letterman replied.

He asked about The Devil Wears Prada, which was met with a slight eye roll. “Well, I seem to remember that the movie was fiction and we really like fiction at Vogue.”

“Right, right,” said the comedian. “Have you ever put anybody in a headlock?”

The lips parted and she shook a bit with laughter. “Maybe you?”  

Mr. Letterman asked if it took money to be fashionable. Ms. Wintour used the opportunity to plug the Fashion’s Night Out shopping event on Sept. 10. But could someone be fashionable on a budget of, say, $20? Mr. Letterman asked. “Well, you can buy lipstick!”

The host gave up and decided to focus on the film. He said he was impressed that in the documentary, certain spreads were being re-shot less than a week before the issue went to press. Is this typical? he asked.

“Absolutely,” Ms. Wintour. replied. “As it is for a TV show. I mean, you guys didn’t even call me till Friday!”

“Wow. It takes you three days to get ready? Big deal!”

Ms. Wintour laughed at this, too, even though her smile went tight and not quite as toothy.

Mr. Letterman was also surprised that the main characters in the film were his contemporaries. “Vogue is not only run by senior citizens,” joked Ms. Wintour, essentially admitting her age (59). “We have a lot of younger people working at the magazine but the director in his wisdom chose to focus on the more mature people working there.”

Mr. Letterman’s next guest was Yankee first baseman Mark Teixeira . Before Ms. Wintour left the stage, Mr. Letterman said that they would hit some balls. “Oh, we are?” she said, and laughed some more. But she didn’t stick around.  

Monday: Late Night With David Letterman

We just can’t wait to see how the big guy handles his lead guest: Anna Wintour. The ever-elegant and chilly editor in chief of Vogue is mysterious, terrifyingly powerful and—even with magazines gasping for existence—as close to royalty in certain publishing circles as you are going to get. But with the release of the documentary The September Issue, a behind-the-curtains look at how the fashion bible is produced (apparently, dissing Sienna Miller’s neck and hair is part of the process!), Ms. Wintour has agreed to appear on Late Night like any other common celebrity to answer Mr. Letterman’s questions. We have so many already! Starting with, what on earth will she be wearing? And does she know how cold Dave likes to keep the studio and to bring a cardigan? Will Dave tell her she smells delicious? We. Can’t. Wait. [11:35 p.m., CBS]

Tuesday: St Elmo’s Fire

Where to start with this movie? First of all, it is not directed by John Hughes but rather auteur Joel Schumacher, though one might be forgiven for being confused. After all, is there a Brat Packier movie than this one? It's got Demi Moore (playing out-of-control wreck Jules. Close your eyes, though, and you’ll swear its Lindsay Lohan. Spooky!), Ally Sheedy, Judd Nelson, Emilio Estevez, Mare Winningham, our 1985 would-be boyfriend Andrew McCarthy, Rob Lowe as awesome sax-soloist Billy Hicks and even Andie MacDowell, who shows up as a (snarf) doctor with super-pretty hair. ABC recently announced that this movie is being turned into a series, which makes us feel somewhat sad … and old. Here’s hoping the gang will still have cause to chant Booga Booga Booga Wah Wah Wah at least once per episode. [7:30 a.m., AMC]

Wednesday: Grindhouse

Congratulations are in order for Quentin Tarantino: His wacky Nazi-hunting Inglourious Basterds is not only a hit with critics, but also No. 1 this weekend at the box office. Today you can catch the 2007 double feature of Grindhouse, which includes Death Proof  (written and directed by Mr. Tarantino) and Planet Terror (written and directed by Robert Rodriguez), if you happen to have a spare 195 minutes. If not, we humbly recommend Death Proof, because the girls are so foxy and badass and we so love seeing Kurt Russell as a homicidal maniac (casting directors take note!). [1:20 a.m., ENC]

Thursday: Models of the Runway

What’s really kind of amazing is that it took the geniuses at Project Runway this long to spin off of their Project Runway cash cow with Models of the Runway. For the uninitiated, there’s always that fun moment in every Project Runway when all the model ladies come out in little black slips, and are forced to stand on the runway like cattle while the fashion designers pick. One is always out. It has brought some great drama in the past (remember “it’s a motherfucking walkoff”? Or when the normally tactful Tim Gunn described one poor soul as having an elongated marshmallow shape?). Last week’s first episode focused on a rather angry redhead, who is clearly going to bring the drama, but we can’t really tell all those skinny bitches apart yet. Tyra should be very, very worried.  [11 p.m., Lifetime]

Friday: There Will Be Blood

Before we get all caught up in Daniel Day-Lewis, song-and-dance man, which we're sure will happen once we see the much anticipated (with the awesome trailer) Nine, let us sit back and remember him as the shadowy, complicated, darkly misanthropic Daniel Plainview in Paul Thomas Anderson’s There Will Be Blood. For the role that won him the Oscar, Mr. Day-Lewis goes deep and really kinda crazy dark! This is a movie that we promise gets better and more interesting with every viewing. Forget the now infamous “I drink your milkshake” line, what about when he puts that napkin over his face? And don't you think he really slapped Paul Dano around for that one scene? This is art! [4:30 p.m., ShoE]