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10 Shows You Need to See This Winter

Here's a preview of what New York theater has to offer in the first quarter of 2019.

Dozens of plays, musicals, and everything in between will open over the next few months. But there's so much to see, and only so much time and money to do so. With that in mind, we're bringing you a list of the most buzzed-about shows this winter. These are the ones we're most excited for — and you should be, too.

The stars of Fiasco Theatre's Merrily We Roll Along in rehearsal.
(© Jenny Anderson)

1. Merrily We Roll Along (begins January 12)
After a creative Into the Woods in 2015, inventive off-Broadway troupe Fiasco Theatre returns to Roundabout Theatre Company to reimagine Stephen Sondheim and George Furth's 1982 musical about the way success impacts the lives of a trio of old friends. While Merrily We Roll Along was last seen in 2012 at Encores!, this staging marks the musical's first full production in New York City since 1994. It's finally "our time" to see it.

Lin-Manuel Miranda and Thomas Kail bring Freestyle Love Supreme to the Greenwich House Theatre.
(© Tricia Baron)

2. Freestyle Love Supreme (begins January 30)
The hip-hop improv troupe cofounded by Lin-Manuel Miranda is back off-Broadway with a new production at the Greenwich House Theater. Hamilton director Thomas Kail helms this 80-minute show and features six performers — Anthony Veneziale, Chris Sullivan, Utkarsh Ambudkar, Bill Sherman, Arthur Lewis, and Andrew Bancroft — who take suggestions from the audience to create fully realized musical numbers. Surprise guest performers may include busy alumni Daveed Diggs, James Monroe Iglehart, Christopher Jackson, and even Miranda himself, so it makes sense that all cellphones will be checked at the door for an experience unimpeded by Instagram.

Jake Gyllenhaal will appear at the Public Theater this winter.
(© David Gordon)

3. Sea Wall / A Life (begins February 1)
Tom Sturridge and Jake Gyllenhaal return to the stage in this double bill of solo shows by their frequent artistic collaborators, playwrights Simon Stephens and Nick Payne. Sturridge stars in Stephens's Sea Wall, a monologue about our need to know the unknowable, while Gyllenhaal performs Payne's A Life, a work that explores how to say goodbye to those we love most. Carrie Cracknell directs this Public Theater production, which not only promises to be one of the most intimate experiences of the young year, but also looks practically guaranteed to sell out.

Debra Jo Rupp in artwork for Manhattan Theatre Club's production of The Cake.
(photo provided by Boneau/Bryan-Brown)

4. The Cake (begins February 12)
One of the timelier new plays to be presented this winter, Bekah Brunstetter's The Cake tells the story of a baker from North Carolina whose faith is put to the test when her late best friend's daughter asks her to bake a cake for her upcoming lesbian wedding. Manhattan Theatre Club's off-Broadway production stars That '70s Show mom Debra Jo Rupp in a performance that has already garnered her multiple awards and a ton of buzz in its several regional appearances.

Kelli O'Hara and Will Chase in a promotional image for Kiss Me, Kate.
(photo provided by Polk and Company)

5. Kiss Me, Kate (begins February 14)
Tony winner Kelli O'Hara makes her highly anticipated return to Broadway in a new production of the beloved Cole Porter classic. With a song list that includes the standards "Always True to You in My Fashion," "Another Op'nin', Another Show," and "Brush Up Your Shakespeare," Scott Ellis's Roundabout Theatre Company production boasts a company that also includes Will Chase, Corbin Bleu, and Stephanie Styles, as well as choreography by Tony winner Warren Carlyle. It's sure to be "too darn hot."

Ephraim Sykes, Jeremy Pope, Jawan M. Jackson, James Harkness, and Derrick Baskin in Ain't Too Proud.
(© Matthew Murphy)

6. Ain't Too Proud — The Life and Times of the Temptations (begins February 28)
Playwright Dominique Morisseau makes her Broadway book-writing debut with this new biographical musical about the Motown super group the Temptations. Staged by Des McAnuff and the team behind Jersey Boys, Ain't Too Proud has broken box office records across the country, so get ready, Broadway, 'cause here it comes.

Phoebe Waller-Bridge in the London Soho Theatre production of Fleabag.
(© Tristram Kenton)

7. Fleabag (begins February 28)
Writer-performer Phoebe Waller-Bridge (creator of the binge-worthy TV show Killing Eve) brings her acclaimed solo show – also the basis for her cult-favorite sitcom — to Soho Playhouse for its New York debut. Waller-Bridge, stars in the blistering dark comedy, which follows a woman named Fleabag as she navigates life and sex in contemporary London, while also coming to terms with a recent family tragedy. Soho Playhouse was also home to Hannah Gadsby's Nanette before it became an international sensation, so don't sleep on this one.

Laurie Metcalf is the star of Broadway's upcoming Hillary and Clinton.
(© David Gordon)

8. Hillary and Clinton (begins March 16)
Laurie Metcalf and John Lithgow as the Clintons? Count us in. Lucas Hnath's new comedy at the Golden Theatre looks at the former first lady's troubled 2008 primary campaign against Barack Obama (played by Peter Francis James), but not everything is as it seems. We know how history plays out, but when it comes to this year's awards contest, we're still with her.

Santino Fontana as Dorothy Michaels in Tootsie.
(© Robert Trachtenberg)

9. Tootsie (begins March 29)
For his second show of the spring, Broadway's resident director of musical comedy, Scott Ellis, directs Santino Fontana and a cast of veteran Broadway scene-stealers in this new adaptation of the 1982 Dustin Hoffman comedy. Costarring Lilli Cooper, Sarah Stiles, Julie Halson, and Michael McGrath, this new musical by David Yazbek (The Band's Visit) and Robert Horn (Designing Women) floats to the Marquis Theatre on a jasmine wind of buzz, laughs, and enthusiastic reviews from its Chicago tryout. Time to learn how to walk in high heels.

A scene from the UK production of James Graham's Ink.
(© Marc Brenner)

10. Ink (begins April 2)
A new drama about the rise of Rupert Murdoch will play a Broadway stage that's just an avenue away from the New York headquarters of Murdoch's Fox News channel. Written by James Graham, this West End hit charts Murdoch's rise after purchasing the struggling British tabloid The Sun as he turns it into a sensationalist must-read paper. Bertie Carvel reprises his Olivier Award-winning turn as Murdoch, with fellow Olivier winner Jonny Lee Miller returning to Broadway as Larry Lamb, the paper's longtime editor.


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