At La Jolla Playhouse, ‘The Luckiest’ looks at who sticks around when crisis strikes

When Melissa Ross sets out to pen a play, the “pen” is not just a figure of speech: She writes everything in longhand the first time around.

Those early drafts, Ross says, become a kind of life history of the play. As she puts it: “I keep them so I can go back. So if I ever got lost, I can get back to what that was.”

Getting back to where one began — and grappling with what might’ve been lost — is in some sense at the heart of Ross’ latest play, “The Luckiest,” which is about to receive its world premiere at La Jolla Playhouse.

The time-jumping piece centers on a young woman named Lissette (portrayed by Aleque Reid) who receives a dire diagnosis that turns her life upside down.

But this is not Lissette’s story alone, which is part of the point: “The Luckiest” also looks at the roles that her mom, Cheryl (Deirdre Lovejoy of TV’s “The Wire”), and best friend, Peter (Reggie D. White), play in all that Lissette is facing.

“The themes really are about the times in our life when we need to ask for help from other people,” says Ross, who wrote her first play when she was about 9 years old. “And about our friendships — the friends that are our family, and the family that’s our family. And our relationships with both.

“So in addition to this illness, it really is about how we show up for one another in this world. And how (the three characters) all do that for each other; they all show up for each other in different ways throughout the story.”

The birth of “The Luckiest” has been a bit of a family affair itself: The play was first developed and presented in staged readings last year as part of the Playhouse’s DNA New Work Series, under the direction of Jaime Castañeda, who is also now staging the full production.

It represents a return to the La Jolla theater for Castañeda, who left the Playhouse last year after a fruitful four-year stint as associate artistic chief that included directing such productions as Rajiv Joseph’s “Guards at the Taj” and Mike Lew’s “Tiger Style!”

For Ross — a much-produced playwright, Juilliard School grad and onetime actor who’s a member of New York’s LAByrinth Theater Company — “The Luckiest” also has some origins in a health crisis that once roiled her own life.

About five years ago, the Massachusetts-raised writer was getting into a taxi when she slipped and fell on ice.

“And when I tried to stand up, there was nothing holding my leg together,” she recalls now.

The injury was what Ross describes with a rueful laugh as “the unhappy triad,” meaning she damaged three major supporting structures of the knee.

And that wasn’t the only blow she received: “Around that same time, I also lost some people who were dear to me,” including a beloved grandmother, says Ross.

“So there were scenes of grief, and I was sort of homebound. My mom came and took care of me, which was amazing.

“(And) I was abundantly grateful for the amount of support and help I received at the time — from friends, from family. It was really amazing. I was abundantly grateful for how many people were there me.

“It’s one of those times in your life when you have to stop and regroup and pause. And at the time, I sort of went, ‘I think there’s a play in here!,’” Ross adds with a laugh.

“I didn’t know what it was, but there was something sort of brewing, and I kind of filed it away for the future and said: ‘Someday I’m going to revisit that time in my life.’”

Sickness and health

“The Luckiest” is not the first play Ross has written that deals with illness and its intersection with family issues. Her 2015 work “Of Good Stock,” whose off-Broadway production with Manhattan Theatre Club starred Alicia Silverstone, centered on a woman battling breast cancer.

“The three sisters in the play also lost their mom to cancer,” she says of the piece, which had its world premiere at Orange County’s South Coast Rep, a key artistic home for Ross.

“That play was dealing a lot with legacy, and the things we pass on. The father was an author, so it was dealing with books and the legacy of parents to children — what we pass along and what we leave behind.”

(“The Luckiest” also is not the first Playhouse show in recent years to confront issues of sickness: In 2012, former Playhouse artistic chief Des McAnuff staged the imaginative and hi-tech rock musical “Yoshimi Battles the Pink Robots,” whose heroine was fighting cancer; and last year brought “Hundred Days,” the real-life-derived piece by The Bengsons about health scares, mortality and more. “The Luckiest” cast member White was in that production as well.)

“The Luckiest,” says Ross, spans about 10 years in Lissette’s life, from her late 20s to her late 30s.

And “I don’t think it’s giving away too much to say the play is told non-linearly,” Ross says. “We go to different periods in time, and see these people in different combinations with each other.

“I write a lot about about the family we come into this world with and the family we choose. I have a few plays that sort of deal with those themes. So I think that’s something that’s revisited in this particular play.”

The piece, she adds, is not without its humorous side, despite the sobering themes.

“I never write jokes — if I try to write a joke, I guarantee it will not be funny,” says Ross. “But usually humor comes out of people in very real situations. I think that’s where the humor emerges (here).”

What comes next after the Playhouse for “The Luckiest” is not something Ross seems particularly focused on just now. In her mind, the next chapter in the play’s life has yet to be written — in pen or otherwise.

Her preference is “to be present with where the play is now. It feels like the play is figuring out what it is with this group of people. That first production is really special — the first time it’s really finding its way in the world.

“That’s a lot.”

‘The Luckiest’

When: Previews begin June 30. Opens July 8. 7:30 p.m. Tuesdays-Wednesdays; 8 p.m. Thursdays-Fridays; 2 and 8 p.m. Saturdays; 2 and 7 p.m. Sundays. Through July 28.

Where: La Jolla Playhouse’s Sheila and Hughes Potiker Theatre, Playhouse/UC San Diego Theatre District, 2910 La Jolla Village Drive, La Jolla.

Tickets: $39 and up ($25 and up for military; other discounts may be available)

Phone: (858) 550-1010

Online: lajollaplayhouse.org