The emotional impact of plays about musicians tend to have a high floor and a low ceiling. Heartbreak Hotel, Hank Williams: Lost Highway, Lady Day at Emerson’s Bar and Grill, Always . . . Patsy Cline—it’s a category of theater that’s by and large informative and unchallenging and, at best, an excuse for a solid live revue. These shows also usually feel like they’ve been pressed out of the same Mold-A-Rama with a different name and songbook.

Dael Orlandersmith’s latest monologue, now making its world premiere at the Goodman, does not.

In part, that’s because her central figure, jazz singer Billie Holiday, never appears, and her music is only heard as an accent around the edges. Instead, Orlandersmith explores and grapples with the themes of Holiday’s music entirely through the lens and life of one of her fans. It’s a thoughtful twist on the typical chronological, paint-by-numbers biographical format, and it treats the contributions artists bring to the world as immortal gifts that continue to resonate and communicate long after their creator has passed.

We meet Helene (Linda Gehringer) in her spacious Andersonville home, realistically rendered by set designer Andrew Boyce, as she’s cleaning up after her late husband’s 80th birthday party. She’d been planning the celebration long before the unexpected and aggressive recurrence of his stage 4 stomach cancer, so instead of canceling, she memorializes him with a party he’d have loved, full of wine and cigarette smoke and Danish dishes and nonstop Holiday on the record player.

“I just had a party and everyone is gone” is a common setup for solo shows, but it’s tricky. It’s no doubt a practical solution for how to organically introduce anecdotes about different characters, but its ultimate premise is the idea that the space was, moments ago, occupied by lots of vibrant people you would have loved to meet whom you’ll now be passively told about. This model could probably use some retooling.

Anyway, Helene tells us, as her loneliness creeps back in, “this house is both house and tomb.” But Billie, she says, “is my friend in the dark.” When a loved one dies, years of inside jokes, casual references, and a shared appreciation of particular works of art die with them, but for Helene, the bittersweet passion inherent in Holiday’s voice takes on new meaning, one that provides comfort rather than despair.

About two-thirds into Chay Yew’s production comes a This American Life chapter-length vignette about how Helene met Holiday during her 1954 appearance in Copenhagen, and it’s during this stretch that Lady in Denmark really comes to life. The combination of Stephan Mazurek’s projections, Gehringer’s performance, and Orlandersmith’s storytelling recalls the vitality of Emily Mann’s Having Our Say: The Delany Sisters’ First 100 Years, which has a similar speaking-to-an-audience-directly structure.

But Helene’s monologue is ultimately about death, and the lingering grief that haunts surviving spouses even when they’re afforded a comfortably long life span, a support structure of attentive family and friends, and a lovely home in a vibrant neighborhood full of vintage furniture shops and brunch joints.

That translates into a lot of time listening to a grieving septuagenarian describe a barrage of cancer-related horrors in excruciating detail after excruciating detail in a very quiet theater—the silence is remarked upon at least twice.

From my seat in the back of Goodman’s Owen theater, I wondered how many people in the audience had firsthand knowledge of that despair, and how they could possibly stand to benefit from sitting and stewing in it for so long. Were the iTunes sample-length snippets of thematically parallel Billie Holiday songs illuminating or redemptive enough to justify going through that melancholy?

That wasn’t the case with Orlandersmith’s most recent work, Until the Flood, which handled material audiences should be be agitated about, the enduring crisis of unarmed black men in America being gunned down by police. Although Orlandersmith’s multitude of characters expressed their grief, there was a forward momentum and a sense of urgency and action amid the anguish.

Lady in Denmark is about a quieter struggle, and in its way, it does speak very well to Holiday’s music from a new perspective. Once the drop-in visits from concerned friends vanish, Helene warns us, “This is the beginning of real pain.”

And yet, the quote that sticks with me the most comes not from the play, but from a couple wiping their eyes on the sidewalk outside the theater after the show: “Yesterday, a funeral, and then that?”   v