There are certain actors worth catching in any project they take on, even if, to borrow a now quite dated cliché, it’s reading the phone book. Then there are times when such actors find roles that fit like perfectly tailored suits, and it’s nothing short of cause for celebration.

Well, break out the champagne and the party favors, because a new match has been made in heaven, between a two-time Oscar-winning stage and screen veteran, Dianne Wiest, and a rising playwright, John J. Caswell Jr. In Mr. Caswell’s ingeniously wacky, weirdly moving, altogether wonderful “Scene Partners,” Ms. Wiest is cast as the 75-year-old, newly widowed Meryl Kowalski, who leaves behind Milwaukee and her bleak life to pursue movie stardom at Los Angeles.

Sure, it’s a long shot; as more than one supporting character will note in the play, set in 1985, Meryl is burdened not only by her age but by sharing a first name with Hollywood’s most celebrated actress of the moment. Yet our heroine is undeterred: After threatening an agent with a gun (loaded with blanks), she secures a spot in the class of a prestigious acting coach and director. He’s so impressed by Meryl’s unique voice and sheer grit that he eventually decides to devote a film to her life story.

Or, does any of this really happen? Mr. Caswell has earned acclaim using highly theatrical and even surreal elements to address sobering themes in previous plays such as “Wet Brain” and “Man Cave.” In tackling fame and ambition, as well as mortality, “Scene Partners” offers especially ripe terrain for the playwright and director Rachel Chavkin, whose flair for the darkly fanciful has been evident in musical productions such as “Hadestown” and “Natasha, Pierre & the Great Comet of 1812.” 

For this play, Ms. Chavkin has recruited a video and projection designer, David Bengali, her collaborator on last season’s “The Thanksgiving Play,” who embellishes Meryl’s adventures — or visions — with both old movie and television clips and striking images of the present, meaning the 1980s. That decade is also represented in song — Corey Hart’s maudlin hit “Never Surrender” is a recurring reference — and by other playful touches, like the inclusion of a medical doctor named Noah Drake, named after a popular soap opera character during that era.

Mr. Caswell’s whimsical text also nods further back, to Arthur Miller and Tennessee Williams; Meryl’s ogre-like spouse, we discover, was named Stanley Kowalski, just like the brutish husband in “A Streetcar Named Desire.” “Yes, I know what you’re thinking,” Meryl tells her drama teacher and classmates after disclosing this coincidence. “And I have no idea who’s responsible for feeding the details of my life to Mr. Williams for his little play.”

Ms. Wiest is every bit as wry and marvelous delivering such lines as you’d imagine she’d be, suggesting a character who could have wandered in from one of her sometime colleague Woody Allen’s movies, were he (or most other leading directors, in fairness) to write parts for women her age. Like her castmates here, many of whom juggle two or more roles — Josh Hamilton is a standout as the oily agent and comically eccentric acting coach — she also serves the poignant and sometimes ominous aspects of Mr. Caswell’s story.

In the play’s most chilling scene, which unfolds on video, Meryl is interrogated by a smiling but cold-eyed and aggressive reporter, and we’re reminded how, during this period, seemingly innocuous figures such as Oprah Winfrey and Barbara Walters laid the groundwork for our current obsession with the everyday lives of celebrities — and ordinary people who, like Meryl, are desperate to be celebrities.  

Then again, as Mr. Caswell observes in his playbill notes, “We make things up in life,” because “otherwise there’d be nothing there. … We are inherently creative by necessity of survival.” Occasionally, as “Scene Partners” reminds us, that creativity can be not only entertaining but inspiring.