Twenty years ago, Richard Scheuer Jr. died from a brain hemorrhage at the age of 48. His obituary in the May 12, 1996 New York Times identified him as “a general partner in a Manhattan arbitrage firm who supported education and the arts as a trustee of his family’s charitable foundation.” But his first love, according to his eldest son Benjamin—who’d turned 14 just before his father’s passing—was playing music. The two were not on speaking terms when Richard died, and Benjamin’s lingering guilt over that sad fact has carried him a long way. The Lion, Benjamin’s solo musical about his attempts to whup grief and deadlier diseases, opened at Manhattan Theatre Club in 2014. After winning a Drama Desk Award for Outstanding Solo Performance and enjoying a successful run in London, it’s now ensconced at Arena Stage’s intimate Kogod Cradle, part of a two-year tour.

It’s easy to see why the show has been so popular. Scheuer is a dextrous guitar player (he uses between six and eight of them, most in different tunings, during the show) and an earnest singer. More importantly, he’s an ingratiating, outsized personality, his smile beaming out from between his artfully distressed thicket of sandy hair and his pre-loosened tie. His songs, often liberated from rigid rhyming schemes, are more upbeat than confessional acoustic balladry often is; they tend to be pointed and short, even while permitting lyrics like “You explain what baby acorn squash is / Wearing leopard-print galoshes.”

The show is short, too: A brisk 70 minutes. The dozen-plus numbers are stitched together by banter as terse as a police report, sketching out the conflict between tweener Benjamin and his mercurial dad, his alienation as a young adult from his mom and younger brothers, and the arc of a romance in his 20s. Curiously, these micro-monologues feel like they’ve been workshopped and pruned more fastidiously than the songs have been.

They also elide details that might complicate his portrayal of himself as an indefatigable underdog, like the fact that the unnamed English boarding school his mother sent him to was Eton College, where royals and future prime ministers are groomed, or that at some point during his years back in the States as a not-especially-struggling rock and roller he graduated from Harvard University, as his father had done. Benjamin can hardly be blamed for the privileged circumstances of his birth, any more than he can for the bodily misfortune that befalls him later. He’s free to tell his own story as selectively as he likes, as we all are, and as we all do. Material comfort does not ease emotional isolation. If you feel alone, then you are.

It would be nice if the show acknowledged the material part of it, though, especially once his estranged family moves from England to the U.S. to support him through a terrible trial — the kind that spares no one, but that you’d rather face with resources than without.

The ordeal he describes in this show has now been documented in an album, The Bridge; an art book, Between Two Spaces; and a stage show that will spawn a second album. In the show, he mentions a long convalescent vacation that helped him get his groove back. That’s nice. The person I know best who got sick young had to move in with her parents, and then return to work before she was ready because she couldn’t afford to lose her job.

Again, it would be unfair—that word again—to downplay Scheuer’s talent and charisma on account of the advantages he doesn’t mention. Being rich didn’t save his old man from dying young, it didn’t prevent him from getting sick, and it didn’t make repairing his familial relationships any easier. Money doesn’t make “Cookie-Tin Banjo”— the conciliatory show opener about the toy instrument his father made for him when he was child—any less moving, or the musical’s title song, about learning to draw comfort from your family, any less reassuring.

Does it sound like I’ve convinced myself? I nearly have. The Lion is a marvelous show that seemed disingenuous to me only in hindsight. Maybe there’s a lesson in that, too.

1101 6th St. SW. $45–$70. (202) 488-3300. arenastage.org.