Top theatre to see in New York in May

Discover new Broadway shows and Off-Broadway shows to check out across New York City in May 2023, including star-studded plays, original musicals, and more.

Gillian Russo
Gillian Russo

The month kicks off with Tony Award nominations on May 2 this year. It's the height of the theatre awards season — now that all this season's Broadway shows have opened ahead of the Tonys ceremony, it's campaign time, so keep an eye out for articles, subway ads, posters, and more featuring the hopeful honorees when you're online or walking around the city. But even though there are only a few new Broadway musicals and plays this month, that doesn't mean there's any lack of theatre to see.

You can still catch performances of Broadway shows that opened in April, as they're still running through May and beyond, or be the first to see the earliest premieres in the 2023-24 season. There are also plenty of Off-Broadway shows opening anew, so why not check some of those out and go to a theatre you might not otherwise visit? Here are our picks for Broadway and Off-Broadway theatre to see in May.

Get tickets to a New York show on New York Theatre Guide.

The Sign in Sidney Brustein's Window

Oscar Isaac and Rachel Brosnahan on stage together is already an unmissable event. Put them on stage in a lesser-known Lorraine Hansberry (A Raisin in the Sun) masterwork, and it's even more crucial to go. For 80 performances only, the pair reprises their roles from off Broadway earlier this year as Sidney and Iris Brustein, who face the hard reality that their progressive ideals are unattainable — and could cost them their marriage.

Get The Sign in Sidney Brustein's Window tickets now.

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Grey House

Frights await in the Grey House — that is, the Lyceum Theatre. Enter an abandoned cabin in the mountains with a stranded young couple, who are initially glad for shelter but soon afraid for their livelihoods. Tony and Emmy winner Laurie Metcalf stars as the head of this supernatural household, and her performance — alongside those of Tatiana Maslany, Paul Sparks, Millicent Simmonds, Sophia Anne Caruso, and more — are worth seeing. They're expecting you.

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Once Upon a One More Time

It's Britney, Broadway! We're so lucky that we can hear the Princess of Pop's biggest hits in the new musical Once Upon a One More Time. Fittingly, Britney Spears tunes tell a story about fairytale princesses who create their own happily ever afters once they read The Feminine Mystique. After jamming out at the show once, you'll want to go, baby, one more time.

Get Once Upon a One More Time tickets now.

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King James

Abbott Elementary's Chris Perfetti and Glenn Davis put on a thrilling one-on-one match in Rajiv Joseph's King James. They're not playing basketball, but over the course of the play, the sport — and particularly their love of LeBron James — brings them together and apart. Even non-sports fans will enjoy this show about friendship up until the final buzzer.

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Days of Wine and Roses

The writers of The Light in the Piazza are debuting a new musical for the first time since that Tony-winning hit premiered in 2005. That new musical is Days of Wine and Roses, a bittersweet look at love. Broadway favorites Kelli O'Hara and Brian d'Arcy James star as Kirsten and Joe, a couple struggling to save their relationship and family after falling into alcoholism.

Check back for information on Days of Wine and Roses tickets on New York Theatre Guide.

The Great Gatsby

Join the party, old sport! This immersive adaptation of The Great Gatsby turns the Park Central Hotel New York into Jay Gatsby's lavish mansion, where one of his infamous bashes is in full swing. Don your 1920s best (if you wish) and hobnob with Gatsby, Daisy Buchanan, Jordan Baker, and all the characters from F. Scott Fitzgerald's Jazz Age novel about love, dreams, and glamour.

Get The Great Gatsby tickets now.

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Primary Trust

What if you had the chance to start anew? That's the gist of Primary Trust, a new play by Eboni Booth. When Kenneth is laid off from his bookstore job, upending his rigid routine for the first time in ages, he's encouraged by various characters to go out and explore the wider world he's avoided for so long.

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Bees and Honey

Experience a Washington Heights love story in Midtown. Based on a love song by Juan Luis Guerra, the new play Bees and Honey sees married couple Johaira and Manuel on the brink of career milestones — as well as tragedy. As these new challenges mount and they change as a result, they must discover whether love is enough to keep their once-carefree romance alive.

Check back for information on Bees and Honey tickets on New York Theatre Guide.

Wet Brain

John J. Casewell's new play uses horror and humor to explore loss. A run-down family in a run-down home is dealing with the loss of their patriarch, who has succumbed to alcoholism. The family cope with wisecracks and the knowledge that he may or may not have been abducted by aliens, but they also search for true closure.

Check back for information on Wet Brain tickets on New York Theatre Guide.

The Comeuppance

Join the reunion at Branden Jacobs-Jenkins's The Comeuppance. In this new dark comedy, a group of former classmates meet up before their actual high school reunion to drink and catch up. Grave truths come out as they play games, chat, and realize how much they've all changed, and their only common ground — their time at school — is a bygone memory.

Check back for information on The Comeuppance tickets on New York Theatre Guide.

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