Sam Kissajukian’s performance “300 Paintings” resists easy categorization, and that’s by design. It is one of the most unconventional pieces of art I’ve ever seen in a theater: part comedy set, part TED Talk, part play and part gallery show. In under 90 minutes, Kissajukian narrates how he walked away from a decade in stand-up comedy, crashed into painting and learned to treat his bipolar disorder not as an obstacle to be conquered but as a fundamental part of his artistic identity. I found the experience utterly absorbing in the moment, and it stayed with me long after leaving the theater.
The show, which runs from Oct. 1 to Oct. 25 at the American Repertory Theater (A.R.T.), begins with a hard reset. Kissajukian explains how the stand-up circuit shaped him into a comedian rather than an artist, someone chasing laughs instead of pursuing expression.
As he tells it, quitting sent him into an abandoned cake factory, where a six-month manic period ignited a burst of ferocious, unsustainable creation. The title of the play isn’t metaphorical. Kissajukian produced hundreds of paintings, along with miniatures, dioramas, T-shirts, digital art and business plans. In this creative explosion, he rode a wave that was at once productive and alarming. After its peak came a depressive episode just as intense, finally provoking Kissajukian to seek treatment and support.
Kissajukian is the show’s plot, protagonist and only actor. The aesthetic is stripped down and direct: one person onstage framing paintings and episodes from his life with the timing of a comic and the self-reflection of a playwright. Both the form and the narrative are tough to pin down. He moves from joke to sober reflection to cultural theory, enacting the very volatility he describes.
Early on, he announces that he’s working without a script, channeling the images unfolding in his mind. As a result, the energy, and even the content, can vary with his mental state at any given performance. When I attended, he was quietly witty, with a dry edge.
Crucially, “300 Paintings” rejects the tidy narrative of “overcoming” a mental health condition. Kissajukian does not glamorize bipolar disorder, but he shows how he has learned to harness periods of elevated mood while putting guardrails in place to protect himself and others, including therapy, medication and collaboration. He is upfront in acknowledging harm and recovery. The result is art made neither despite nor because of bipolar, but with it.
Beyond its thematic weight, “300 Paintings” is often bitingly funny. I erupted in laughter as Kissajukian described pitching an absurd business plan to a hedge fund investor who gamely sent him a five-figure check. He promptly blew the advance buying out Kmart’s clearance stock of black T-shirts (which he bleached with the label “Pisscasso”) and amassing a cache of out-of-circulation World War II-era Australian pennies for use as currency in a virtual art museum. The antics Kissajukian recounts are so surreal that I found myself wondering if they could really be true, before realizing I was missing the point.
Humor is personal, and some of Kissajukian’s jokes unsettled me as much as they amused me. There are also moments that may feel opaque if you’re not familiar with stand-up as a craft or with the pressures of the industry. Kissajukian puts viewers in the awkward position of laughing as he details how stand-up audiences can exploit performers, erasing the artist behind the act. A short detour explaining why he uses humor in “300 Paintings” and how those dynamics differ might have clarified his critique of stand-up, though at the risk of breaking the momentum and intimacy. It is a tension that lies at the core of the show. In a nightclub, humor can substitute for real connection; in a theater, it can foster it.
I found “300 Paintings” insightful, frequently hilarious and deeply moving. If you’re deciding whether to go, it’s important to know what the show isn’t. It’s not a traditional play with scenes and supporting characters, nor is it a stand-up hour engineered for easy laughs. It’s one performer telling his life story, folding painting, comedy and confession into a singular, personal work that may change how you look at humor and art.
