What to see in New York in May

Here's our top picks of theatre to check out in May 2021.

New York Theatre May 2021

With smaller New York theatres opening across the city, audiences are now returning to live entertainment once more. Last month, Perfect Crime, the longest-running play in New York history, reopened its doors in April 2021. Mayor Bill de Blasio declared Perfect Crime as the “official return of New York City theatre" — theatre is definitely back. 

New York theatre in May continues to be a mix of streaming offerings, as well as in-person productions. Here’s our top 10 theatre picks for May 2021.

Underground Cabaret

Live theatre, tick. Burlesque, tick. A three course meal, tick. Underground Cabaret is the one-stop shop for all things New York entertainment in May 2021, with award-winning burlesque artists, aerialists and variety acts taking to the stage. While you’re watching the action unfold, you’ll also dine on Israeli cuisine, created by Miznon celebrity chef Eyal Shani. This show really has it all.

Underground Cabaret, from May 1. Underground Cabaret tickets are on sale now

Rooftop Movie Musicals

We’ve spent over a year binge watching television series and films on repeat. Now you can reunite with friends and family at a rooftop movie musical and make memories together. Film musicals being shown in May 2021 include Chicago, West Side Story, Cabaret and Cats. All audience members will be given a pair of headphones to watch the movie, so if you’re singing out loud with the film, then nobody can hear you.

Green Room 42, from May 6. Rooftop Movie Musicals tickets are on sale now

Waiting for Godot

Samuel Beckett’s famed drama will receive a new and virtual lease of life in May 2021, thanks to The New Group’s upcoming season. Ethan Hawke and John Leguizamo will star in the production, setting out to to “collaborate in a hybrid, on-screen world, finding a way to make a play newly alive for themselves.”

Online, from May 6. More information here

Restart Stages at Lincoln Center for the Performing Arts

Lincoln Center for the Performing Arts (LCPA) will be welcoming hundreds of theatregoers to their new outdoor venues as part of their latest festival. 24 events will take place throughout May, with highlights including a Norm Lewis concert, choral performances, poetry readings and presentations from Juilliard. An extra bonus; they’re free to attend.

LCPA, from May 10. Restart Stages at Lincoln Center for the Performing Arts lottery tickets are available now.

Watch on the Rhine

Broadway’s Best Shows Spring ‘Spotlight on Plays’ series continues with two virtual offerings this May. Up first is Lillian Hellman’s Watch on the Rhine, directed by Sarna Lapine. The World War Two drama follows an American family realize the fatal consequences of Nazi ideals spreading globally.

Online, from May 13.


American novelist Jodi Picoult is part of the creative team for Breathe, a series of musical presentations all about love during the pandemic. Five duos will star, including real-life couples Patti Murin and Colin Donnell and Matt Doyle and Max Clayton. Breathe comes ahead of the Jodi Picoult book Between the Lines at Second Stage Theater.

Online, from May 14. More information can be found here

Miscast 2021

MCC Theater’s annual Miscast gala sees some of Broadway’s biggest names take on roles they’d never typically perform. It’s online for a second year, but you’ll still be treated to exciting performances from Annaleigh Ashford, LaChanze, Billy Porter and Idina Menzel to name a few. Once you’ve seen a Miscast gala, you’ll never hear some musical theatre songs in the same way again.

Online, from May 16. Miscast 2021 tickets are on sale now

The Freedom Series

During the pandemic, we’ve spent most of our time cooped up indoors, locked away from the world. As events begin to happen again and we can reunite with friends and family, what does it mean to be free? Exploring how the human body reacts to freedom, choreographer Francesca Harper’s newest work will encourage audiences to be in tune with themselves once more.

The Green-Wood Cemetery, from May 19. The Freedom Series tickets are on sale now

The Sisters Rosensweig

If you haven’t been able to see your sisters during the pandemic, why not organize a virtual screening together to watch The Sisters Rosensweig. Wendy Wasserstein’s family drama tells of three sisters who reunite, with direction from Anna D. Shapiro and starring Kathryn Hahn.

Online, from May 20.

NY PopsUp

Okay, we don’t know where and when NY PopsUp events are happening in New York City. We’re not sure who’ll be starring in them either. One thing is for certain though. They’ll be showstopping. So far, Broadway theatres have been open for one-off performances, with stars including Nathan Lane, Savion Glover and Amber Iman returning to the stage. 

We’re looking forward to upcoming NY PopsUp performances in May 2021.