Chelsea resident Katie Holmes.

If a typical break-up calls for vats of Ben & Jerry’s and repeated viewings of The Notebook, then we suppose a highly publicized divorce from a top Hollywood actor and devout Scientologist calls for a cross-country move and a gorgeous new apartment. That’s pretty much what Katie Holmes got last summer when she took up residence at the Chelsea Mercantile—the spectacular, star-infused, 21-story building at 252 Seventh Avenue. The actress reportedly signed the lease just a few days after announcing her split from husband Tom Cruise in June 2012.

As you might expect from Ms. Holmes, who has also transmitted her fashion sense to daughter Suri, these are some stylish digs. The actress has been settling into her New York lifestyle pretty well since then. Last winter, Ms. Holmes took the stage as Lorna in Theresa Rebeck’s Dead Accounts, which ran from late November to early January at the Music Box Theatre. Though the show received mixed reviews, Ms. Holmes’s performance stood out, at least to The New York Times. Ms. Holmes “appears much more at ease playing a worn-down country mouse to the hyped-up city mouse of [Norbert Leo Butz],” Ben Brantley wrote. “Ms. Holmes and Mr. Butz summon an appealingly natural family rapport … You may even forget that Ms. Holmes is Katie Holmes for a moment.”

It’s no problem that Dead Accounts closed earlier than expected—Ms. Holmes is already at work acting in another project, a Spike Lee production called Mania Days. In the film, which has been shooting in different locations around New York City, Ms. Holmes plays Carla, a manic-depressive poet who forms a romantic relationship (and later a pregnancy) with a manic-depressive rapper, played by Luke Kirby.

Katie and Suri strolling and riding.

If you’re looking to spot Ms. Holmes on the streets of New York City, it’s unlikely—the star leads a private life (or as private as possible when you are being stalked by paparazzi). The most reliable place to spot the celeb is the H. Stern store on Fifth Avenue, where larger-than-life, nearly nude billboards of the gorgeous Ms. Holmes grace the windows on either side of the doors. Since moving to New York, Ms. Holmes has also been made the face of Bobbi Brown; she’s the company’s first-ever celebrity spokesmodel.

When Ms. Holmes isn’t performing onstage or posing on-camera, she’s playing the role of mother to daughter Suri. Ms. Holmes reportedly enrolled the stylish seven-year-old in the prestigious Avenues school, located near their home in Chelsea.  The school is very new, and has an educational philosophy that might appeal to jetsetters able to pay its slightly higher-than-usual tuition costs.

“In addition to teaching traditional subjects,” Avenues CEO and co-founder Chris Whittle has said, “the school takes seriously its mission to prepare students for the world through intensive classes in Spanish or Mandarin and by providing them with a global view of geography, history, religion, demographics and economic development across many cultures and countries.”

We always knew that Suri could out-dress us any day, but from the looks of her new school, we’re pretty sure she’ll soon be able to outsmart us, too.

But Back to Those Digs

The Chelsea Mercantile was originally built as a fabric manufactory in 1908 (that’s exactly 90 years before the premiere of Dawson’s Creek, the show that marks Ms. Holmes’ debut, in case you slept through that pop culture moment). Nowadays—with the influx of trendy galleries, restaurants and shopping spots in the neighborhood—the historic textile building has been transformed into more than 350 luxury condos that house the likes of Marc Jacobs, Jane Fonda and Lance Bass, along with Katie and Suri. It boasts an interior garden, full gym, parking garage, and a 10,000-square-foot roof deck, and yet still retains charming elements of its turn-of-the-century origins.

“The Chelsea Mercantile is really cool,” says Corinne Pulitzer, executive vice president of Douglas Elliman Real Estate, which has sold a number of units at the Chelsea Mercantile in recent years. “The building has the infrastructure of a factory building, with the very high nine-foot ceilings. Some of the apartments have exposed brick walls.”

Sensible Katie probably chose the apartment for the distinctly downtown flavor but slightly

Entrance to the Chelsea Mercantile, home of Holmes.

more convenient location. She’s not a kid anymore, after all. “The apartments have a loft feel, but you don’t have to go down to Soho or Tribeca, which I think is a big pull for people,” Ms. Pulitzer says. “It’s great to live down there, [but] it’s a hard lifestyle selection if someone’s in the theater, or [working] in midtown.”

The Chelsea Mercantile is also perfect for anyone with a seven-year-old daughter. “The building has a children’s playroom,” says Ms. Pulitzer. “I can see how [Ms. Holmes] came to choose it.”

The diversity of the Chelsea neighborhood may also be responsible for attracting celebrities like Ms. Holmes. From the threshold of the Chelsea Mercantile, residents can reach avant-garde art galleries, elite eateries and fine retail all on foot (or by chauffeur, of course). “The neighborhood has such diverse attractions that it gets a really good mix of different types of people who are seeking [something] cool and edgy,” Ms. Pulitzer says, “as opposed to the Upper East Side, which I wouldn’t call cool or edgy.”

The Star Grocery Shops, Too

On the ground floor of Ms. Holmes’s apartment building is a cozy Whole Foods Market, where the actress is known to regularly shop. The Daily News photographed her there last summer, trying on  cowboy hats with daughter Suri as the pair shopped for a Fourth of July meal.

Though she had been spotted inside the organic food mecca, reporters last summer—who crowded Ms. Holmes’s building shortly after she moved in—were wondering why they rarely spotted their target entering Whole Foods. Hillary Reinsberg, a staff member at BuzzFeed, explained the popular theory that gradually circulated among the crowd of Holmes seekers: “Nearly every lingering photographer seemed to have figured out that Holmes has a way of getting into the store from inside her swanky apartment building,” Ms. Reinsberg wrote in a July 2012 article.

We needed to know: Is it a secret revolving bookshelf, activated by touching a certain tome? Does she enter through a nondescript girls’ bathroom, á la Harry Potter and the Chamber of Secrets? Can Katie Holmes teleport?

We ask a Whole Foods employee if Ms. Holmes really has a private entrance to the grocery store. He laughs—he has heard the rumor before. But, he says, there’s definitely no secret entrance for the rich and famous. “There’s no Batcave in here, there’s only one door.” Like almost everyone else we spoke to for this story, except the vocal Ms. Pulitzer, the real estate agent, this employee declines to be named, citing company policy.

While Ms. Holmes shops at Whole Foods, her “team” reportedly favors the more casual deli across the street. According to Amen, who does give his first name, and works behind the counter at Chelsea Gourmet Deli, “She sends her bodyguard in every morning—it’s one major guy who comes in.” He notes that the bodyguard frequently buys sandwiches, drinks and snacks.

And when it comes to eating out, Ms. Holmes has no shortage of choices in Chelsea. “The restaurants—my God, you never have to cook!” Ms. Pulitzer gushes.

Back in Beverly Hills, Ms. Holmes was known to be a fan of Crumbs Bakery. Luckily for Ms. Holmes, she can feed her sweet tooth on the East Coast, too; there’s a Crumbs a block away from her Chelsea apartment.  And indeed she has visited the cupcake shop. “It wasn’t a big interaction, but she was very nice,” says the manager of Crumbs when asked about Ms. Holmes’s visit to the bakery. She admits feeling a little star-struck: “I pretended like it wasn’t Katie Holmes!”

Nearby is also the trendy Meatpacking District, whose cobblestone streets are clustered with the hottest bars and restaurants in the city. “I’m sure [Ms. Holmes] hangs out there a lot,” Ms. Pulitzer says. “You have the Ganesvoort, all of these fabulous hotels and clubs. The Standard is there too, and they have that beer garden in the summer. It’s a really high-energy neighborhood.”

Living the Active Life

Of course, for a celebrity with a physique like Ms. Holmes’ and modeling and film contracts, along with great cupcakes come great demands for cardio. Though Ms. Holmes ventures outside of Chelsea to attend spin classes at SoulCycle, the actress is also known to frequent the Chelsea Piers, an expansive, multi-purpose athletic complex along the Hudson River, just blocks from her apartment, although this might be more for Suri’s benefit than her mother’s. Last summer, photographers spotted Ms. Holmes taking Suri to a Chelsea Piers gymnastics class.

If Suri tires of gymnastics, there’s always ice skating to try (and adorable skating dresses to wear while doing it), golf, bowling, boating and facilities for just about any kind of kid party.

But there is at least one sport Ms. Holmes enjoys partaking of at Chelsea Piers. An employee at Chelsea Brewing Company—a microbrewery and restaurant that’s part of the Chelsea Piers—says that Ms. Holmes is reportedly quite the alley cat.

“She goes bowling,” the employee says. “What’s interesting is they offer the private room—they have a private room with eight lanes—but they don’t want it. They want to be in

Crumbs, a favorite of Katie's and Suri's.

public.” Bowling in plain sight. Pretty brave.

Shopping Around

Ms. Holmes is known to be a long-time fan of Anthropologie; lucky for her, the store has a retail space in Chelsea Market, an easy walk from Ms. Holmes’s apartment.

We swing by Anthropologie’s Chelsea location in the hopes of spotting the actress—or at least finding out if she’s a frequent visitor. A friendly employee confirms our suspicions, noting that Ms. Holmes often comes into the store to grab a few things. “She’s a loyal customer,” the sales representative says. “She’s an Anthro girl!”

One Columbia grad student and frequent Anthropologie shopper describes the time she and her roommate spotted Ms. Holmes at the Chelsea Market store: “I was admiring bowls and glasses and first saw her from the periphery,” the source says. “I walked over to my roommate and asked her to look for me again to confirm. Katie Holmes said, ‘Let’s go, sweetie’—she was with Suri, and they were looking at plates. I also checked out next to them and she asked about different colors for table settings.”

The student also reports that on that day in November, Ms. Holmes’s overall style was pretty casual. “From what I remember, [she wore] a long gray cardigan, jeans and short boots,” she says.

Ms. Holmes has also been seen checking out other spots in the famed indoor market, which houses popular joints like Morimoto, Friedman’s Lunch and Sarabeth’s Kitchen.

Walk a little farther south to the Meatpacking District and you’ll hit even more high-end clothing shopping destinations: Diane von Furstenberg, Tory Burch, Alexander McQueen and Stella McCartney all have shops there. And the shopping options are only continuing to grow: “On the corner of 14th Street toward the West Side Highway, one of my favorite gas stations is now going to be 20,000 square feet of retail right by the Highline,” Ms. Pulitzer says. It’s a market that’s certainly perfect for a fashionista like Ms. Holmes—or even a budding fashionista or a budding one.

jtaylor@observer.com

Will Sheila Nevins' eighth apartment at the Chelsea Mercantile be her last? Stay tuned! (Patrick McMullan.)

When Sheila Nevins first started at HBO as "Director of Documentaries," the cable network had only done one, and she only signed a 13-week contract. Over three decades later, and save for a three-year diversion in the ’80s, Ms. Nevins is still at HBO, and is still heading up the channel's documentary division. We can only hope the contract she just signed at the Chelsea Mercantile has as much staying power.

And this is nowhere near Ms. Nevins’ first purchase in the condo building. In fact, it’s at least her eighth.

Ms. Nevins, who has produced shows like Real Sex, along with less salacious fare, began buying up units in the Chelsea Mercantile at 252 Seventh Avenue back before city records were digitized. But her interest in the building dates back to at least 2004, when she picked up a one-bedroom on the sixth floor for just under $1.1 million. This was before Nick Jonas, Lance Bass, Marc Jacobs and Jane Fonda—and eventually Katie Holmes, who rented a unit in the building right after she split up with Tom Cruise (Suri goes to the Avenues School just down the street, a draw for many of the Chelsea Mercantile’s new bold-faced names)—made the building the most star-studded in Chelsea.

Ten years and more than a dozen property transactions later (Ms. Nevins has been gradually offloading her units—at least four of which she’s owned over the years—at the Channel Club building on East 86th and York) she has graduated to the penthouse—a two-bedroom duplex penthouse, to be exact, that she picked up for $4.5 million, according to city records.

The two-bedroom unit (easily converted back to a three-bedroom) was “beautifully renovated” by its previous owner—Carmelo Starrantino, according to city recordes—said Pamela D’Arc with Stribling, who had the listing, and it also has a “dramatic” glass staircase leading to the master bedroom on the unit’s second floor.

The building also contains a feature that may attract attention-shy celebs: a private garage. “You can access the garage without leaving the building,” Ms. D’Arc told The Observer. Celebs still have to slum it in the elevators like everyone else, but “most celebrities in the building tend to stare at their iPhones while in the elevator,” a resident told the New York Times.

Celebrities—just like you and me!

Katie Holmes and Mayor Michael Bloomberg at The New York Observer's 25th anniversary party.

Last Thursday evening at New York’s perch of power dining, the Four Seasons Restaurant, billionaires could be found clinking glasses with politicians, actors could be seen rubbing shoulders with news correspondents, and throngs of notable wordsmiths quaffed copious amounts of liquor at The New York Observer’s 25th anniversary soiree.

“I think this is the best collection of New Yorkers I’ve seen in 20 years!” effused Ronald Perelman, who leered lustily at our highball glass.

“Can I ask you one question?” he continued. “Where’s the bar?”

It’s thataway, just behind Katie Couric, we assured the business tycoon. Or if he preferred, he could hit the bar on the other side of the restaurant’s famous pool room, where Harvey Weinstein had posted up and Spike Lee, who declined to take off his puffy coat, had helped himself to the generous spread of gourmet goodies before chatting up Katie Holmes and Donald Trump.

(Sadly, Shindigger caught only the tail end of that conversation. Mr. Lee saying to Mr. Trump: “Well, that’s one thing we can agree on.”)

Observer editors past and present—Peter Kaplan, Elizabeth Spiers and Ken Kurson—circled the room, while publisher Jared Kushner greeted guests with wife Ivanka Trump at the door. And from the worlds of business, politics, entertainment, fashion and beyond, the stars just kept pouring in. Even Mayor Michael Bloomberg was impressed with the turnout. “The Observer does throw a hell of a party,” he said in his opening remarks, before dubbing attendee Cory Booker “the handsomest mayor in America—west of the Hudson River.”

Here came Terry McDonell and Danny Strong and Jay McInerney and Audrey Gelman and Larry Gagosian and Ray Kelly and Joel Klein and George Pataki and Eric Schmidt and Kevin Ryan and—oh my!—Rupert Murdoch.

We just had to talk to Rupert Murdoch

“Mr. Murdoch? Mr. Murdoch?” Shindigger beckoned.

“What?” said the cantankerous billionaire, walking right on by with wife Wendi Murdoch.

“Can we ask you a few questions, sir?”

“No!” barked Mr. Murdoch, before making a dramatic swat in our direction. Shindigger agilely ducked for safety, silently chuckling at the news baron’s aversion to the press.

In no time at all, we found friendlier prey. “Someone from The Observer already observed me,” said Broadway favorite Christine Baranski, who was chatting with fashion consultant Fern Mallis under the floral protection of one of the poolside trees.

“New York is just the coolest city, and I love the fact that this paper really makes New York seem cool,” Ms. Baranski said. “The Observer touches on the sophistication and fun of the city. I just like the tone of it.”

Just then, we re-encountered Mr. Perelman, who had been paired with a cocktail, and who had his own take on The Observer. “The only bad moment I ever had was when they wrote a story about a little synagogue,” Mr. Perelman said, referring to Chloé Malle’s prickly 2010 article about the billionaire’s lavish private synagogue.

“I wish they didn’t, but they did, so that’s the end of it,” he said. “I still love The Observer, even besides that.”

Very gracious, we thought, bumping then into Observer alum George Gurley, with whom we had pre-gamed earlier in the evening at Jean and Martin Shafiroff’s glitzy Saint Patrick’s Day cocktail party. The suavely fuddled Mr. Gurley made the perfect VIP-fixer for Shindigger when PR maven Peggy Siegal was hand-holding elsewhere.

“He does Shindigger, he’s trustworthy,” Mr. Gurley assured José “Pepe” Fanjul, the president of Fanjul Corp. and Florida Crystals Corporation.

“I think this is the best event!” exclaimed Mr. Fanjul’s Carolina Herrera-clad wife, Emilia Fanjul.

We danced past the couple then to catch up with model Hilary Rhoda, who was getting a kick out of the bash.

“Oh, it’s a great party!” she said, holding a plate of Christian Albin’s Italian gourmet cibo. “I love the room, it’s gorgeous. I love the band. Obviously getting into the food situation.”

Ms. Rhoda, also dressed in a Carolina Herrera creation, had just returned from the runways of Paris, where she had walked for Céline. “Now I’m back and on photo shoots,” she said.

Photorealistic artist Chuck Close was also taking advantage of the buffet.

“I love The Observer almost in spite of myself,” he said. “At first it was a guilty pleasure, and then one day they endorsed Mitt Romney. I almost canceled my subscription. What were they thinking?”

What brought you back onboard, we wondered?

“When I go to Europe and can’t read you, I get really upset,” he confessed. “It went from being a guilty pleasure to a real pleasure.”

A cocktail later, we found ourselves yelling: “Ms. Herrera, we saw you at the School of American Ballet’s Winter Ball, and you were dancing!”

Shindigger had never witnessed her quite so zippy.

“Yes, I know. I’m South American,” Carolina Herrera retorted sassily.

Cuchi-Cuchi!

Back to the bar we traipsed.

“Do you have a white wine or champagne?” Padma Lakshmi pressed a barman.

“Rosé or brut?” he asked.

“Brut,” the foodie stated assuredly.

Ms. Lakshmi wanted to know our thoughts about her Blossom Ball. “Did you have fun?” she asked.

“We did, “Shindigger said.

“I’m glad!” she said. And then the Maison Martin Margiela-wearing TV host told us about the previous day, which she had spent in Albany: “I was recognized by the State Senate. Every State senator was there, because it’s budget time,” she dished, lowering her voice to a serious, husky tone. Though she lost us at “budget.”

When the band was replaced by DJ Chelsea Leyland’s turntables, things had officially strayed, and Shindigger was impressed (and a tad disappointed) that not a single sloshed attendee plummeted into the white marble pool. Cases in point: when perpetually grabby Four Seasons proprietor Julian Niccolini began frisking two attractive slabs of meat, offering to shower them with pricey pours of Bordeaux. Or when Gawker founder Nick Denton resorted to flirting with a pride of hungry tech lionesses, having already refused to be photographed with Mr. Murdoch because “it’s too obvious.”

Shindigger sidled up to the bar for last call with Ashleigh Banfield of CNN and Fox News’s Kimberly Guilfoyle.

“We’re together,” Ms. Banfield joked about their warring media outlets. “I’ve known her for eight years. We use to work at Court TV together.”

“Did you see Rupert Murdoch? He didn’t want to talk to us,” we bemoaned.

“Because I work at CNN, he didn’t want to talk to me, either,” said Ms. Banfield.

“No, he’s great! God bless him!” Ms. Guilfoyle cut in, right on cue.

As Rihanna’s “Diamonds” thundered over the speakers, Ms. Banfield revealed that she had gotten a smooch from the Newark mayor.

“We had a Cory Booker sandwich,” swooned Ms. Guilfoyle.

As things were wrapping up, at least one guest took on a reflective air. Mr. Close told us that he was overwhelmed by the turnout and notable faces. “I’ll make sure to be at the 50th anniversary,” he promised. “I’ll be 98.”

Shindigger likes a man who can forecast that far ahead—or, for that matter, with any type of math skills.

Here’s to the next 25 years!

Jared Kushner, Katie Holmes and Mike Bloomberg (PMc)

- The intimidatingly assiduous Peggy Siegal greets people at the door; thanks us for coming to celebrate party with The New York Observer. "We are The New York Observer!" We cry. She doesn't even pause. "Well, it's great to see you anyway."

-Terry McDonell: I've always loved the Observer, I have great respect for Peter Kaplan. The coverage of everything I was interested in New York in the past 25 years was reflected in The Observer at the highest level.

- Ray Kelly recalls the last time he was at the Four Seasons. "[We] feel like you never leave," we tell the Police Commissioner. His reply: "A lot of people feel that way."

- Spike Lee keeps on puffy coat all evening, talks to Katie Holmes, Donald Trump. Catch tail end of his conversation with Mr. Trump: "Well, that's one thing we agree on."

- Mayor Bloomberg gets onstage, proceeds to riff about slipping Harvey Weinstein a script (Bloomie on Bloomie), Cory Booker ("The handsomest mayor West of the Hudson") and The Observer ("It's OK when you needle somebody else, but not me.")

- Michael Shannon confounds half the party with his celebrity status. "What famous person is that?" we are asked more than several times. We finally after give up and refer them to Boardwalk Empire after several of our "the Future General Zod" joke receives blank stares.

- Nick Denton refuses to take photo with Rupert Murdoch because it's "too obvious."

-Chuck Close: I love the Observer almost in spite of myself. At first it was a guilty pleasure. When I go to Europe and can't read you, I get really upset.

- Mayor Cory Booker meets Manhattan Borough President Scott Stringer’s press secretary/Girls actress Audrey Gelman. Mr. Booker finds a way to bring the conversation back around to Star Trek.

- Game Change’s Emmy-winning screenwriter Danny Strong still getting recognized for his years on the TV show Buffy the Vampire Slayer. But he's a good sport, and challenges fanboy to name the one episode of the hit show that was nominated for an Emmy. (Answer: "Hush.")

-Former editor Peter Kaplan begs off with the excuse that he is trying to wean himself off of anti-anxiety medication.

-Ronald Perelman: I love the publication! I think everybody here is great. I think this is the best collection of New Yorkers I've seen in 20 years!

- Jay McInerney inquires about the after-party; never shows up.

The Four Seasons Restaurant, 99 East 52nd Street, (212) 754-9494, 6:30-9:30pm, by invitation only.

'Grace' star Paul Rudd

Chaplin

Barrymore Theatre

Opens September 10

In the footsteps of the Judy Garland biographical play End of the Rainbow tramps Chaplin, a musical about the life of Chaplin. Unlike other attempts to illuminate the lives of showbiz legends--a subgenre that also includes Master Class’s portrayal of Maria Callas--Chaplin is to have a cast of 22 in what surely will be splashy musical numbers. Rob McClure, previously of Avenue Q and, well, the La Jolla out-of-town tryout for Chaplin, takes on Charlie in a production that is likely to showcase every element of the actor’s legendary film career but for the silence.

Grace

Cort Theatre

Opens October 4

Paul Rudd, suddenly more prolific than he’s ever been with TV and film gigs, is headed back to Broadway. (He previously played second fiddle to Julia Roberts in Three Days of Rain--but now he’s the star!) Mr. Rudd is to play one-half of an innocent couple moving to Florida in order to start religious-themed motels; his better half is to be played by Kate Arrington, whose real-life partner, Oscar nominee Michael Shannon, joins the fracas as the pair’s new neighbor, while legendary TV fixture Ed Asner plays an exterminator. (With all these mainstream stars, is this a Broadway show or the SAG Awards?)

Cyrano de Bergerac

American Airlines Theatre

Opens October 11

It’s been five years since the last Broadway production of Cyrano de Bergerac, and theater writers have been storing up nasal puns since then. (Who nose if this will be a success? We’ll be sniffing for hints from the producers! Etc.) Tony-winner Douglas Hodge straps on the prosthetic nose for the title role of the lovesick, prohibitively ugly French nobleman, while Clémence Poésy is to allure as Roxane, the not-so-obscure object of desire, and onetime Spider-Man villain Patrick Page makes us all glad he survived that production as he plays Cyrano’s erstwhile ally Comte De Guiche. We smell a good night at the theater!

Who’s Afraid of Virginia Woolf?

Booth Theatre

October 13

To celebrate the fiftieth anniversary of Edward Albee’s rollicking domestic nightmare, the New York stage welcomes a production by way of Chicago and Washington. Tracy Letts, who moonlights as a Pulitzer-winning playwright, is to take on George, while Steppenwolf star Amy Morton (previously, too, a Tony nominee for Mr. Letts’s August: Osage County) has been honing her piercing shriek as Martha. Both actors appeared in the original production, which earned raves from local critics--and surely they’re ready for the big time--the three-hour play is the sort of marathon you can only really train for by two years and three cities’ worth of practice.

'Dead Accounts' star Katie Holmes

The Heiress

Walter Kerr Theatre

Opens November 1

Taking over the role of Olivia de Havilland and Cherry Jones? That’d be ultra-fast-rising starlet Jessica Chastain, who, like Paul Rudd, is taking a break from her prolific film career to portray Catherine Sloper. Catherine, originally a character in Henry James’s novel Washington Square, possesses that Jamesian fragility, shyness, and moth-to-flame attraction to callous villains; the character is set to inherit an enormous fortune, but is so taken aback at the love of a churlish fellow that she may just squander it all. Ms. Chastain’s Broadway debut will be watched closely by all those who love and/or envy her, but with support including castmate David Straitharn and director Moisés Kaufman, Ms. Chastain may not return to her day job anytime soon.

Annie

Palace Theatre

Opens November 8

Little girls of New York, begin beseeching your parents for tickets. After a long search, the producers of what may become the season’s most lucrative revival found their girl--preteen brunette Lilla Crawford is to strap on the red wig and belt out “Tomorrow” in the latest Annie. Though it’s toured the U.S. frequently, the saccharine show hasn’t been seen on Broadway since its 1997 revival. It’s not entirely for kids: James Lapine, a frequent collaborator of Stephen Sondheim’s, is to direct the production, while two-time Tony winner Katie Finneran assays the role of Miss Hannigan. Ms. Crawford, get former red-wig-wearer Sarah Jessica Parker on the phone to discuss how to be deal with newfound fame!

Glengarry Glen Ross

Schoenfeld Theatre

Opens November 11

Al Pacino, who starred in the film production of Glengarry Glen Ross as young, robust Ricky Roma, is showing his age: he’s coming to Broadway this season as Shelley Levene. Levene, scholars of David Mamet will surely recall, is the once-great real estate salesman who has grown unable to generate good leads (much as an actor of Al Pacino’s caliber has, for years until just now, been unable to get a lead on a role that required much more than senseless bellowing). The cast is rounded out by the high-toned likes of Bobby Cannavale and Richard Schiff; the “Coffee’s for closers” monologue is from the film and not the play, but we can dream it’ll be included.

Rebecca

Broadhurst Theatre

Opens November 18

Daphne du Maurier via Alfred Hitchcock via Christopher Hampton! The well-loved playwright and screenwriter has adapted into English the book of a musical that played Vienna in the mid-2000s, recounting the twice-told tale of a second wife who must confront the ghost of her new, controlling husband’s former wife. As in du Maurier’s novel, the naive protagonist is never named but for “I”; Jill Paice is to attempt to make a name for herself in the role. The directors are about as prestigious as Mr. Hampton; Michael Blakemore won two Tonys for directing a play and a musical in the same year back in the day, while Francesca Zambello is an opera director with, one presumes and hopes, a flair for the dramatic.

Dead Accounts

Music Box Theatre

Opening Date November 29

When we think about Broadway’s breakout ingenues of the past decade, our minds don’t immediately leap to Katie Holmes’s turn in All My Sons in 2008. She was... fine? Certainly her time in New York, and exposure to paparazzi therein, engendered a high-water mark in the sales of “boyfriend jeans” nationwide. But the stage is apparently a safe place for Ms. Holmes, as it’s to Broadway she returns for her first new role post-extremely-notable-divorce. The midwestern woman trying to start over while living with her parents is to play a midwestern woman trying to start over while living with her parents. Well, Ms. Holmes is from Toledo and her character’s from Cincinnati. And her parents, we read, are in off and on. No matter--the play’s by super-prolific Theresa Rebeck, and could allow for a Kidmanian career renaissance.

The Anarchist

Lyceum Theatre

Opens December 2

A new work on Broadway playing blocks away from a revival of his best-loved work, and a daughter who’s one of those TV Girls? Could things get sweeter for David Mamet? Well, there was the little matter of actress Laurie Metcalf dropping out of the role of a women’s-prison warden in The Anarchist, the newer of his two currently produced plays--but no matter. Debra Winger removed herself from exile to drop in for the role, and Patti LuPone, playing a radical prisoner pleading for her own parole. Mr. Mamet’s neoconservative bent may well inform just how we see the role of the anarchist played out onstage, but we’d forgive Mr. Mamet anything!

Kim Kardashian expected at FNO. (Getty Images)

It's already time for Fashion Week again? How did that happen? And not just Fashion Week, but the one that includes New York's annual Fashion's Night Out event. This evening marks the third-most important night of the year for Anna Wintour (besides the Met gala and whenever the president is in town), and we're looking forward to all the celebrity sightings that are sure to occur. Here are our five best guesses of A-list names to appear tonight.

1. Ryan Lochte: The Olympic swimmer was already spotted last night at the Joseph Abboud menswear show at the New York Public Library ... marking the first and last time you will ever see "Ryan Lochte" and "public library" in the same sentence. We just hope he'll be able to pick up some styling tips and avoid future disasters like this one. (We should have known Mr. Lochte would show up at any event that promised a sighting of Kanye West.)

2. Katie Holmes: The recent hermit is making her first appearances at New York's Fashion Week. Her Holmes + Yang fashion collaboration with stylist Jeanne Yang is getting its first Lincoln Center runway show. In the meantime, she's already shown up at the Style Awards, held last night in the same location, presenting the "Designer of the Year" award to Caroline Herrera, so there's a good chance she'll be sitting front-row at her show. Not to mention that she's just been announced as the face of Bobbi Brown Cosmetics. Looks like life's good after Tom.

3. Sarah Jessica Parker: Now that she's such good friends with Anna Wintour and Oscar de la Renta, how could the star prepare for an upcoming Glee cameo anywhere else?

4. Kim Kardashian: She'll be taking a break from talking about the economy on CNBC to tackle fashion at Lord & Taylor tonight. (She'll be there selling her new perfume, True Reflection.)

5. Pippa Middleton: O.K., it's a long shot, but there's a possibility that Kate's sister will stick around post-birthday/U.S. Open and see all the beautiful people at Fashion Week. Especially since she's having so much fun juggling the men here.

My, how things change!

The unwilling Vanity Fair cover girl and tabloid culture's summer star is to appear in the new play Dead Accounts, which just announced its full cast. Ms. Holmes has surrounded herself with a coterie of respected performers significantly less renowned for non-artistic endeavors. The male lead is Norbert Leo Butz, a two-time Tony-winner; the other stars are prolific character actress Judy Greer, Coast of Utopia star Josh Hamilton, and Tony nominee Jayne Houdyshell, who just appeared in Broadway's Follies.

It seems that Ms. Holmes is interested in reinventing herself as a real Broadway actress--that All My Sons, with its all-movie-star cast and classic script, was a significantly  safer bet than Dead Accounts. Since the newly divorced, newly intriguing actress is sure to sell tickets on her own merits, choosing a new play with less famous performers is a good way to use her fame for good--all while ensuring she'll be the one in the spotlight throughout.