Some may see May as the month when theater people are waiting for the Tony Awards in June, but don’t be fooled. There are at least 21 shows opening in New York this month, including one on Broadway. AND there are a half dozen major New York theater awards announcing their winners in May. Below is a list of May awards by the date when the winners are announced, and May shows organized chronologically by opening date, with descriptions. Each show title is linked to a relevant website. (And each award is linked to a list of nominees — for those awards that announce nominees in advance.) Nothing, of course, is guaranteed about any of these shows, even those that seem the most promising. (This is why I write reviews.) There are always surprises. Color key: Broadway: Red. Off Broadway: Purple. Off Off Broadway: Green. Awards: Orange
May 2
Love Me (Funny Sheesh at The 4th Street Theater) It’s the mid-1990s in New York City, and underachieving writer/motivational speaker Charlie Styptic searches for love and artistic achievement.
May 4
New York Drama Critics Circle winners announced
Fred and Estelle Astaire nominees announced Forever (New York Theatre Workshop)
Framed with the story of the pilgrimage that Dael Orlandersmith took to the cemetery where Marcel Proust, Oscar Wilde and Jim Morrison are buried, she offers a semi-autobiographical exploration of the family we 
are born into and the family we choose. Dinner With The Boys (Theatre Row – Acorn) Written by and starring Dan Lauria (The Wonder Years, Lombardi), this comedy tells the story of two wise guys from the old neighborhood who find themselves at odds with the Family, and prepare them dinner to make amends.
May 5
Theatre World Awards announced
Toast (The Public Theater) Lemon Anderson (County of Kings) tells the story of a group of inmates “fighting to keep their minds free amidst the 1971 riots that rocked Attica Prison.”
May 7
Melissa’s Choice (Theatre Row, The Lion) A passionate lawyer must decide between two men, and is helped by her unlikely guides at a local campsite. Cool Hand Luke (59e59) Under the scorching Florida sun, Boss Godfrey watches the chain gang and keeps his eye on Cool Hand Luke – war hero, trouble-maker, and inspiration to his fellow inmates – just the kind of man the Boss needs to crush. (They make no mention of the Paul Newman movie. Both are based on the novel by Donn Pearce.)
May 9
Summer and Smoke (T. Schreiber Theatre Studio) The Tennessee Williams play is directed by Terry Schreiber
May 10
Lucille Lortel Awards ceremony
One Hand Clapping (59e59) Adapted from Anthony Burgess’ (author of ‘A Clockwork Orange’) 1961 novel, this darkly comic story about the winner of a TV quiz show who makes a sinister proposition to his wife.
May 11
Outer Critics Circle winners announced
The Painted Rocks at Revolver Creek (Signature) A new play by Athol Fugard inspired by the life of outsider artist Nukain Mabusa.
May 14
The Glass Menagerie (47th Street Theatre) The Tennessee Williams play presented in the inaugural season of the Masterworks Theater Company. The multicultural cast includes Olivia Washington, Denzel Washington’s daughter, as Laura.
May 15
Drama League Awards
May 17
What I Did Last Summer (Signature Theatre) The latest in the Signature season of plays by A.R. Gurney: With her husband overseas near the end of World War II, Grace fights to save the splintering bonds of her family by taking her teenage son and daughter to spend the summer on Lake Erie. Starring the fabulous Kristine Nielsen, with the up-and-comer Noah Galvin.
May 18
Obie Awards
The Flick (Barrow Street Theatre) A new production of last year’s Pulitzer Prize-winning play by Annie Baker about three employees of a movie theater. (My review of original production.)
May 19
The Way We Get By (Second Stage) Amanda Seyfried and Thomas Sadoski in Neil Labute play about the morning after a one-night stand.
May 20
Permission (MCC Theater) Written by Robert Askins (playwright of Hand to God), directed by Alex Timbers: A couple’s new commitment to “Christian Domestic Discipline” upends their lives.
May 21
The Other Thing (Second Stage Uptown) Kim is a journalist, writing what she thinks will be a run-of-the-mill article about a father and son team of ghost hunters in rural Virginia.
May 24
Incognito (MTC at New York City Center) A new play by Nick Payne (Constellations) about a pathologist who steals the brain of Albert Einstein; a neuropsychologist embarks on her first romance with another woman; a seizure patient forgets everything but how much he loves his girlfriend
May 28
An Act of God (Studio 54) Jim Parsons stars in a ” 90-minute comedy where the Almighty and His devoted angels answer some of the deepest questions that have plagued mankind since Creation.”
Cagney (York Theatre Company) A musical about the actor from his humble beginnings in New York City’s Lower East Side through his rise as a vaudeville song-and-dance man, to his superstardom in Hollywood.
May 31
Drama Desk Awards
R/Evolution (Robert Moss Theater) A new musical set 150 years in the future, when governments have been replaced by corporations.
