To produce a play about suffering, Kevin O’Leary hired two men who have suffered more than most.

In an all-male version of “King Lear” opening this week, O’Leary cast Charles Michael Howard in the title role of a tired monarch going mad and Tony Reilly as the beleaguered Earl of Gloucester. The recent lives of both actors have been marked by tragedies the depths of which, O’Leary suggested, only Shakespeare could measure.

Reilly and his wife of 20 years, Susan, were driving from their home in South Portland to New York for the Christmas holiday in 2014 when a truck crashed into Reilly’s car on the Massachusetts Turnpike. Susan died, and Reilly suffered multiple injuries, including the loss of his left leg, which was severed in the accident. He was in a coma three weeks and in rehab for months, learning, among other things, how to walk with a prosthetic leg and how to live without his beloved Susan.

In January 2015, as Reilly lay in a coma in Massachusetts, Howard’s wife of 40 years, Carol, was diagnosed with ovarian cancer. She died March 24. One week later, still reeling from grief and fighting his way forward, Howard crashed his car driving from his home in Kennebunk to teach a night class at the University of New England in Biddeford. Among the injuries he suffered was a shattered left femur. He spent months in rehab, learning, among other things, how to walk with an 18-inch rod running through his upper left thigh and how to live without his beloved Carol.

O’Leary brought together these two men, both friends of his, because he wanted to help them heal.

Charles Michael Howard and Tony Reilly

“King Lear” gives them the opportunity to make sense of their pain, he said. The play, opening Thursday at the Portland Ballet Studio Theater, is Shakespeare’s most disturbing family drama about a ruler whose descent into madness diminishes his desire to lead and destroys his family and the lives of those around him. It includes one of Shakespeare’s most desperate lines, spoken by Gloucester, who has been blinded by his enemies and reeling from loss: “As flies to wanton boys are we to th’ gods, They kill us for their sport.”

Apart and simultaneously, Howard and Reilly have suffered their wives’ deaths and the loss of their own flesh and blood, and are grieving on stage because that’s what good actors do. “We’ve all lost. We’ve all suffered.” O’Leary said. “Some of us check in, some of us check out. Michael and Tony have chosen to live, and are choosing to live.”

Howard said the role of King Lear was “God-sent.”

“All of the past experiences of loss can come into play,” he said.

Gloucester is Lear’s trusted elder who is at odds with the younger generation of the court, including his own sons, who betray him. As an actor, Reilly trained to summon grief. Since Susan’s death and his long and painful recovery, grief comes naturally. “Now it doesn’t take much to get me to that place,” he said. “Emotional grief is the fuel of so much.”

The seeds of this production were sown on the streets of New York, where Howard and O’Leary traveled to see English actor and playwright Mark Rylance in twin productions of “Richard III” and “Twelfth Night” late in 2013. Rylance presented the shows back to back, afternoon and evening, with the same all-male cast in a format known as “original practice,” where men play all the roles as they did in Shakespeare’s day.

O’Leary was mesmerized by the energy of the cast and asked Howard if he could do an all-male version of any Shakespeare play, what would it be? Howard answered “King Lear,” because of the enormity of the role. Because of the lyrical complexity of Lear’s lines and his flight into madness, it requires mental dexterity and physical stamina. It also requires the experience of an actor seasoned on stage and in life. Howard had played the role once before, at Mad Horse several years ago, and he wanted another crack at it. Even before his personal tragedies, he told O’Leary he could bring “a sense of truth” to the role.

Charles Michael Howard, left, and Kevin O’Leary rehearsing a scene from King Lear.

The play was supposed to happen a year ago. Howard had begun reading with O’Leary, director Daniel Burson and other members of the cast when his wife received her diagnosis and died less than three months later. O’Leary postponed the show, enabling him to fill another role in Howard’s life: Savior.

“I do believe he saved my life,” said Howard, 69. O’Leary and other friends helped Howard to walk again, encouraging him mentally and supporting him in material ways, like building a ramp at Howard’s Kennebunk home to make it easier to get in and out during rehab.

The play itself gave Howard something to focus on other than his own personal grief and loss, while also providing a channel for expressing those emotions.

As producer, O’Leary’s job is to bring together the creative team of actors and directors with funders, who share the producer’s vision for the play. He arranges the details, including booking the performance space, handling publicity and ticket sales, and coordinating rehearsal times and locations.

Kevin O’Leary

O’Leary, who plays the Fool to Howard’s Lear, had specific ideas for this version of “King Lear.” Inspired by Rylance and his company, O’Leary wanted to do an all-male version that was loyal to Shakespeare’s language and spirit, and he wanted to recruit Portland’s most committed Shakesepearean actors to help him.

In addition to Howard, Reilly and O’Leary, the cast includes Rob Cameron, Ian Carlsen, Peter Brown, J.P. Guimont, Corey Gagne and Mark Rubin. Burson directs.

The men who play Lear’s daughters dress as women. It’s a simple set, with a few props and an occasional bench or chair. It is set in a non-specific time period. As the play’s elders, the characters of Lear and Gloucester dress more traditionally, while the rest of the cast wears contemporary costumes.

On the 400th anniversary of Shakespeare’s death and following the display of Shakespeare’s First Folio — the earliest compilation of Shakespeare plays, published in 1623 — at the Portland Public Library in March, O’Leary wanted to build something grand. A Portland native, O’Leary, 57, teaches drama at Morse High School in Bath. He’s an actor, director and playwright. He’s also a cheerleader for the theater community, which he calls “the tribe.” He attends about 50 plays a year, posting reviews and words of encouragement on Facebook to other actors and theater companies. His goal is to create “good energy” for theater in Portland and around Maine. “I know how hard it is to do theater, and I know what people have to sacrifice to be artists,” he said.

It was in that spirit that he launched “Lear,” to create a platform for actors to do their best work on a play that demands their best work. More than that, he wanted to mount a play that helped the Portland theater community heal. Through its “kaleidoscopic view” of grief and anguish, “Lear” enables us to make sense of pain, he said.

Charles Michael Howard, left, and Tony Reilly in rehearsal.

Cameron, artistic director of Fenix Theatre Company, which will produce “Much Ado About Nothing” at Deering Oaks this summer, said working on “Lear” has been enlightening. The real-life losses suffered by Howard and Reilly have infused rehearsals with urgency, he said. “I think that these losses served to bring the show to fruition by the urgent need to celebrate life and recovery and find a new normal through doing what Michael and Tony, and really all of us in the cast, love doing most in our lives: Making theater,” he said.

During a recent rehearsal, Dramatic Repertory Company Artistic Director Keith Powell Beyland stopped by to watch. Beyland suffered a stroke last year, and is working to rebuild his life. His stroke and recovery are another part of the Portland theater community’s story of loss these past 18 months.

As Beyland watched, Howard and Reilly worked out theatrical grief, their characters embrace at center stage, one comforting the other, trying to make sense of a world gone mad and “this great stage of fools” while acknowledging their mistakes, their shortsightedness and their humanity.