'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!