May brings new plays with big names. Here are 10 Chicago theater picks for the month.

Want to see a great performance this month? Here are 10 solid options, from splashy musicals to gritty new dramas.

In the world premiere of “Judgment Day,” Jason Alexander of Seinfeld fame portrays a sleazy lawyer who’s visited by an angel, played by Candy Buckley.
In the world premiere of "Judgment Day," Jason Alexander of Seinfeld fame portrays a sleazy lawyer who's visited by an angel, played by Candy Buckley. Courtesy of Liz Lauren / Chicago Shakespeare Theater
In the world premiere of “Judgment Day,” Jason Alexander of Seinfeld fame portrays a sleazy lawyer who’s visited by an angel, played by Candy Buckley.
In the world premiere of "Judgment Day," Jason Alexander of Seinfeld fame portrays a sleazy lawyer who's visited by an angel, played by Candy Buckley. Courtesy of Liz Lauren / Chicago Shakespeare Theater

May brings new plays with big names. Here are 10 Chicago theater picks for the month.

Want to see a great performance this month? Here are 10 solid options, from splashy musicals to gritty new dramas.

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May brings new works with big names, from “George Costanza” as a shady lawyer at Chicago Shakespeare to former popstar Michelle Williams in a pre-Broadway musical reimagining a cult classic. Michael Shannon will once again take the stage in Chicago, and it will happen in a storefront theater that puts audiences up close to the two-time Oscar nominee.

I’m excited for the shows that may get a little weird, such as the new musical parody of every musical ever from Hell in a Handbag Productions. I’m also ready to see all three shows with playwright/actress “Nambi E. Kelley” in the credit lines. May will also have tear-jerkers about sisterhood — oh, and a play about white people trying to create a non-offensive Thanksgiving play. Whatever you may be into, I’m sure this list will have you covered.

Here are our top 10 theater picks for the month of May. Thoughts? Suggestions? Tell us at arts@wbez.org

The debut play by Rob Ulin, 'Judgment Day' runs through May 26 at Chicago Shakespeare.
The debut play by Rob Ulin, ‘Judgment Day’ runs through May 26 at Chicago Shakespeare. Courtesy of Liz Lauren / Chicago Shakespeare Theater

Judgment Day

Where: Chicago Shakespeare Theater

When: Through May 26

In yet another world premiere, Emmy- and Tony-award winner Jason Alexander, best known for his iconic role as George Costanza in Seinfeld, will make his Chicago stage debut as a morally corrupt lawyer being threatened by eternal damnation. This witty comedy covers themes of religion and morality and strives to answer the philosophical question: Are people good or bad? WBEZ’s Courtney Kueppers caught up with Alexander for an interview here.

If you go: 800 E. Grand Ave., tickets from $41

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Death Becomes Her

Where: Presented by Broadway in Chicago at Cadillac Palace Theatre

When: Through June 2

The Academy Award-winning film from 1992 is now a musical. Tony-nominated Broadway star Megan Hilty will grace the stage in the lead role formerly played by Meryl Streep on screen, and Tony-nominated Jennifer Simard will play the former role of Goldie Hawn. But not to be overshadowed, Grammy-winner and former Destiny’s Child member Michelle Williams will play Viola Van Horn, the mysterious woman wielding a magical potion. This pre-Broadway tryout will give Chicago audiences the first look at the musical adaption of the cult classic about an aging actress who finds a way to achieve immortality.

If you go: 151 W. Randolph St., tickets from $29.50

The cast of Thanksgiving Play (from left) includes Nate Santana, Audrey Francis, Paloma Nozicka and Tim Hopper.
The cast of Thanksgiving Play (from left) includes Nate Santana, Audrey Francis, Paloma Nozicka and Tim Hopper. Courtesy of Joel Moorman / Steppenwolf Theatre

The Thanksgiving Play

Where: Steppenwolf Theatre

When: Through June 2

This Broadway hit written by MacArthur “Genius” award winner Larissa FastHorse places four well-intentioned theater people in an elementary school and tasks them with creating a non-offensive Thanksgiving play. This satirical comedy offers a criticism of “woke” American culture through a viewpoint not often seen — the pen of an Indigenous woman. FastHorse said in pre-show interviews that she was told in the past that her plays were uncastable because the characters were Native American. So she placed the issues she cared about in the voices of white-presenting characters. This should be fun.

If you go: 1650 N. Halsted St., tickets from $40

The Midwest premiere of 'Jump' runs through June 1 at Theater Wit. Pictured here is actor Jazzma Pryor.
The Midwest premiere of ‘Jump’ runs through June 1 at Theater Wit. Courtesy of Liz Lauren / Shattered Globe Theatre

Jump

Where: Presented by Shattered Globe Theatre at Theater Wit

When: Through June 1

I saw this Midwest premiere on opening night, and it was a treat. Secrets are revealed, forgiveness is earned and a few tears are shed in a delicate story of two sisters experiencing love, loss, and critical friendships. I appreciated how the heavy subject matter was presented in a digestible way. Characters experienced trauma, but it was never overwhelming, and there are moments of joy and laughter that happened between sisters.

If you go: 1229 W. Belmont Ave., tickets from $15

Michael Shannon returns to A Red Orchid for the world premiere play 'Turret,' written by Chicago playwright Levi Holloway.
Michael Shannon returns to A Red Orchid for the world premiere play ‘Turret,’ written by Chicago playwright Levi Holloway. Taylor Glascock for WBEZ

Turret

Where: Presented by A Red Orchid Theatre at Chopin Theatre

When: May 2 - June 9

Excitement is building over this world premiere, which stars character actor extraordinaire Michael Shannon back on stage in Chicago. Set in the Pacific Northwest woods, this story, described by the theater as “a claustrophobic carnival of carnage,” follows two isolated soldiers stuck in a time loop as they figure out whether the enemy is outside or inside their bunker. Read more here.

If you go: 1543 W. Division St., tickets from $45

'Poor People the Parody Musical' is a mash-up of the genre and will include plenty of familiar showtunes.
‘Poor People the Parody Musical’ is a mash-up of the genre and will include plenty of familiar showtunes. Courtesy of Rick Aguilar Studios / Hell in a Handbag Productions

Poor People the Parody Musical

Where: Presented by Hell in a Handbag Productions at the Chopin Theatre downstairs

When: May 2 - June 16

This world premiere is not your average musical. But it does parody most of your favorites. Set in a gritty New York city, this song-filled production follows an orphan fleeing from her horrible mother (played by Sydney Genco). While embarking on a farcical journey that leads through a magical manhole, the young orphan meets characters and sings songs you may loosely recognize from Annie, Oliver Twist, Les Miserables and Sweeney Todd, just to name a few.

If you go: 1543 W. Division St., tickets from $25

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Native Son

Where: Lifeline Theatre

When: May 10 - June 30

Based on the novel by Richard Wright, this adaptation tells the story of Bigger Thomas, a 20-year-old living on Chicago’s South Side who struggles to find his place in the world. Penned by Nambi E. Kelley, who says Native Son was her favorite book as a child, this powerful play presents Wright’s story to a new generation. 

If you go: 6912 N. Glenwood Ave., tickets from $25

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English

'English' is making its Chicago premiere at the Goodman.
‘English’ is making its Chicago premiere at the Goodman.

Where: Goodman Theatre

When: May 10 - June 9

This 2023 Pulitzer Prize winner was a hit Off Broadway and is now making its Chicago premiere. Four students in Iran are studying for an English test. Passing this test is the key to medical school, reuniting with family, and other life-changing opportunities. Through games, puzzles, and experiences, audiences discover whether learning English will build these students up or break them down.

If you go: 170 N. Dearborn St., tickets from $15

The third and final play in playwright Joshua Allen's trilogy opens at Raven Theatre on May 16.
The third and final play in playwright Joshua Allen’s trilogy opens at Raven Theatre on May 16. Courtesy of Dean La Prairie / Raven Theatre

The Prodigal Daughter

Where: Raven Theatre

When: May 16 - June 22

This world premiere is the third and final play of the Grand Boulevard Trilogy written by Chicago native Joshua Allen. Set on the South Side during the Red Summer of 1919, this story follows a woman who comes back home to Chicago to visit her family. Unresolved feelings and family tension meet hot weather and racial conflicts, creating a pressure cooker of emotions sure to boil over onstage.

If you go: 6157 N. Clark St., tickets from $35

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Stokely: The Unfinished Revolution

Where: Court Theatre

When: May 24 - June 16

This world premiere, also penned by Nambi E. Kelley (read more about the playwright here), follows civil rights activist Kwame Ture (born Stokely Carmichael) as he rises to prominence. The story is historical, but digs deeper than Ture’s political identity to explore who he was as a person, and to shed light on the people who assisted and guided him on his ascent.

If you go: 5535 S. Ellis Ave., tickets from $23.50