At about this time each year, the Chain Winter One-Act Festival showcases new works by established and emerging artists. The headlining program this year consists of three short plays performed in roughly 90 minutes; they include the New York premiere of a piece by a renowned playwright, David Rabe, who has a long association with the Chain Theatre — an independent company promoting locally based talent — and a world premiere from another noted stage and screen veteran, Lyle Kessler, best known for “Orphans,” a searing tragicomedy that has been a vehicle for such stars as Albert Finney and Alec Baldwin.

The first and most entertaining entry in this trilogy, though, was written by the Chain’s literary director, John Arthur Long, who is less widely known. Provocatively titled “The Robot, The Spy, and the Love of A.I.,” it focuses on three characters, only two of them human; Robie, the other, is a robot, voiced by David Rey and physically represented by the Unitree G2 Pro Quadrupled robot dog, operated by Dariel Garcia, in its theatrical debut.  

Mr. Long poses a question that’s also being addressed uptown in “Maybe Happy Ending,” a gorgeous new musical that had its premiere on Broadway last fall: What if robots were to develop emotions? In this case, Robie develops a sort of crush on one of his operators, a young woman called Melanie; the device prefers to call her Melody, singing the name to convey its affection, and gives itself a goofy nickname as well.

Melanie is, understandably, a bit unnerved by the attention, particularly when Robie begins describing, graphically, aspects of male-female intimacy for which it feels anatomically unequipped. Yet when it’s revealed that Melanie’s caddish supervisor, Trevor, is using her and Robie for his own secret agenda and with sinister intent, both the woman and the robot are moved to protect each other.

Guided by the Chain’s artistic director, Kirk Gostkowski, human actors Monica Park and Gabriel Rysdahl prove fine foils, with Mr. Rysdahl’s aggressively obnoxious, leering Trevor underlining Ms. Park’s low-key sweetness as Melanie. Predictably, though, it’s Robie who steals the show; not only does the gadget get some of the best lines, but its movement, alternately suggesting a loyal canine companion and an overexcited frog, can be as touching as it is hilarious.

Mr. Kessler’s “Brothers” is a more traditional, low-tech affair. Like “Orphans,” it features a pair of siblings in a tough spot, though in this case the circumstances are less twisted and, crucially, there’s no dark humor in their predicament — or none that I could find, at least. The setting is a college dorm, where Van sits staring dreamily into space until interrupted by the arrival of his brother, Mark, a medical student who has interrupted his own studies at the behest of their parents.

What follows is a desperate negotiation, as Van, who has given away his possessions and generally creeped out the authorities on campus with his behavior, rambles on about Gandhi and the Buddha and Mark tries to convince him, without offending, that he needs help. Whether Mr. Kessler is suggesting there’s reason in Van’s madness becomes increasingly insignificant as the exchange grows more excruciating, with the siblings begging and battling each other.

Under Mr. Kessler’s direction, Connor Chase Stewart and Chistopher Cortez Adams give robust, stirring performances as, respectively, Mark and Van. But the play delivers tension without relief, or catharsis.

Mr. Rabe’s contribution, “By the Look of Her,” offers more levity, but also more bitterness, and the combination can seem awkward. The author of plays such as “Hurlyburly” and “Sticks and Bones” has proven adept at channeling uglier aspects of the human condition and our search for meaning into satire; here the playwright introduces a family that is drawn together, reluctantly, when its matriarch, Clara, falls into a diabetic coma.

An element of absurdism is immediately established when the sole doctor available can’t be tracked down, and Clara’s devoted daughter, Lorna, seems skeptical that any of her relatives will show up either; her husband, for instance, seems more interested in watching a sporting event on TV. There’s also a brother, a World War II veteran — the play is set in 1963 — who like Lorna speaks to the audience periodically.

Clara is (spoiler alert) eventually revealed to be such a monster that you can’t really blame any of them, and Sachi Parker gets to have some nasty fun in the role. The other actors are less fortunate, especially Christina Elise Perry, who as the long-suffering Lorna is saddled with a monologue that stretches on and on, becoming ever more depressing. By the end, I was feeling nostalgic for that robot.

More information about the festival, including other programs, is available at chaintheatre.org.