Orlando Bloom Swoons, Sierra Boggess Sings Britney & Late-Night Double Trouble in This Week’s Datebook

What’s going on in New York City? The Broadway.com Datebook has you covered! From Orlando Bloom’s Broadway debut in Romeo and Juliet to two world premieres at the Pershing Square Signature Center, the coming week is filled with theater-related things to see and do. Read below for lots of fun ideas!


MONDAY, AUGUST 19
SIERRA BOGGESS IS PART OF YOUR WORLD
The lovely and talented Sierra Boggess is back on the New York stage, and this time she’ll be singing a few of her favorite tunes at theater hotspot 54 Below. No word on which songs the Little Mermaid and Love Never Dies alum will include on her setlist, but we’ve got our fingers crossed we’ll hear a few Phantom of the Opera jams, with a touch of Britney Spears thrown in for fun. Catch Boggess’ solo show through August 26.

ALSO: Annie Golden sings Sondheim Unplugged at 54 Below; Julie Halston brings Classical Julie to Birdland; Tony winner Hugh Jackman chats on Late Night With Jimmy Fallon; Tony winner Catherine Zeta-Jones stops by The View.


TUESDAY, AUGUST 20
IT TAKES TWO AT THE SIGNATURE CENTER
Not one, but two plays will make their world premiere at off-Broadway’s Pershing Square Signature Center today: The Old Friends, a play by Horton Foote receiving its posthumous debut, starring Betty Buckley and Lois Smith; and stop. reset., a new work by Regina Taylor. The Old Friends tells the story of two Texas farming families, while stop. reset. explores the fate of a book publishing company in the digital age.

ALSO: Jenni Barber begins performances as Grace Farrell in Annie; Boardwalk Empire season three, starring Broadway vet and Emmy nominee Bobby Cannavale, now available on Blu-ray; Ethan Hawke heads to The Late Late Show With Craig Ferguson.


WEDNESDAY, AUGUST 21
AWAKEN THE AMERICAN DREAM
Clifford Odets’ Awake and Sing! is reborn at The National Asian American Theater Company, which is celebrating their 24th-anniversary season with a new revival of this 1935 family drama. Awake and Sing! tells the story of a lower-middle class family struggling to make ends meet in a Bronx apartment during the Depression. The production will play through September 8.

ALSO: Spring Awakening alum Robi Hagar performs a concert version of his musical Captive Eyes at the Bitter End.


THURSDAY, AUGUST 22
A DOUBLE DOSE OF BROADWAY ON JAY LENO
The Tonight Show With Jay Leno will get a taste of the Great White Way when Tony winner Kristin Chenoweth and Tony nominee Josh Gad stop by the show on the same night! Gad is plugging his new film Jobs, while Chenoweth will chat about her appearance on the season premiere of Say Yes to the Dress. Even so, we demand fully staged musical numbers, lots of jazz hands and a 13-minute long tap number.

ALSO: Adam Chanler-Berat headlines Bromance in Concert at Joe’s Pub; Harlem’s Big Otis Jump Up Blues Revue, starring Tony winner Lillias White, is in full swing at Ginny’s Supper Club.


FRIDAY, AUGUST 23
JACKÉE MAKES HEADLINES
Emmy-winning star Jackée Harry is spreading the news as the newest addition to the cast of off-Broadway’s NEWSical the Musical. After hilarious stints on TV’s 227 and Sister, Sister, Harry will make ‘em roll in the aisles in the spoof tuner through August 27 at the Kirk Theatre. The show is constantly updated with new jokes and sketches, so now is the time to catch NEWSical for a second side-splitting time.


SATURDAY, AUGUST 24
ORLANDO BLOOM DRIVES CONDOLA RASHAD WILD
Summer may be almost over, but things are getting steamy at the Richard Rodgers Theatre, where an updated production of Romeo and Juliet (with motorcycles!) begins previews. Starring screen heartthrob Orlando Bloom as Romeo and two-time Tony nominee Condola Rashad as Juliet, the new mounting features an all-star ensemble cast that includes Jayne Houdyshell, Chuck Cooper, Roslyn Ruff and Justin Guarini.

ALSO: Cougar the Musical creator Donna Moore steps into her own show.


SUNDAY, AUGUST 25
LAST CHANCE TO MEET TOM DURNIN
The compelling drama The Unavoidable Disappearance of Tom Durnin is closing at the Laura Pels Theatre, and now is your last opportunity to catch Steven Levenson’s play about a family struggling to connect after their patriarch is released from prison. The Roundabout Theatre Company production stars David Morse, Sarah Goldberg, Christopher Denham, Lisa Emery and Rich Sommer.

ALSO: Vanya and Sonia and Masha and Spike plays its final performance on Broadway; I Forgive You, Ronald Reagan and The Designated Mourner close off-Broadway.