FOR FOUR YEARS, playwright Leslye Headland worked as an assistant for studio executive Harvey Weinstein, and watching her play Assistance at Theatre Vertigo, it’s difficult to forget this fact.

Assistance deals with a familiar scenario: a soulless New York office environment where entry-level employees do the bidding of an equally soulless boss—a brilliant, awful man named Daniel Weisinger, who never appears onstage but who is definitely Meryl Streep in The Devil Wears Prada (while also bringing to mind petulant nouveau riche tech bros like Jeff Bezos and Elon Musk).

Headland’s dialogue is fast and quippy, and it takes a while to settle into it for both audience and performers—but when it’s working, it’s highly entertaining. The cast, too, is uniformly strong, and it’s nice to see Jenn Hunter, whose improv skills I adore, in the mix with Vertigo mainstays like R David Wyllie and Tom Mounsey. Wyllie and Kaia Maarja Hillier play Nick and Nora (yes, those are their names), assistants to the invisible Daniel, as they gradually implode over three years of workplace misery. But while the characters are miserable, the audience can’t be, and there are enough jokes and moments of human connection in Headland’s script, effectively teased out by director Brenan Dwyer, to keep things interesting. Supporting players Clara-Liis Hillier and Heath Hyun Houghton both inject some humor into the whole morose proposition as Nick and Nora’s fellow assistants whose dedication to their jobs borders on pathological. There are also some endearing design choices, like a soundscape comprised of all of the electronic nuisances we’ve grown to accept as part of our everyday lives, and an ongoing low-tech sight gag involving a growing pile of crumpled papers.

This delightful confluence of neuroses is disrupted by some genuinely WTF moments now and again—I’m not convinced a final dance number was strictly necessary, and a sex scene in profile through a window will never not be porny. But in capturing the monotonous emotional labor of a sad desk life spent in service to a domineering personality, Assistance succeeds almost a little too well. It gave me flashbacks to the bizarre string of poorly compensated J-O-Bs I had in my early twenties, limbic territory I’m not interested in revisiting for too long.

But given that a 2013 Gallup study found that only 30 percent of US employees report that they genuinely enjoy their jobs, a miserable work life is clearly a systemic, distinctly American problem. However uncomfortable, it’s worth a visit.