On an oppressive late-August afternoon in Los Angeles, Brian Bress and I sit together in front of his computer screen watching It's Been A Long Day, one of two videos that will debut in less than two weeks as part of his first solo show at Cherry and Martin. Clocking in at approximately two minutes, the video features an unnamed sad sack (played by Bress) looking in a mirror and tending to a weeping bullet hole in the middle of his forehead. Poking at the wound with clumsy fingers and muttering to himself in a voice that will certainly keep the flies away, Bress's character quickly refocuses his efforts from caring for the wound to painting his face with it.

Still from It's Been a Long Day, 2009. Courtesy the artist and Cherry and Martin.

Just when I expect that the piece will settle into a jab at painters and painting, I lean in and look again. A series of sly reveals—prostheses peeling from the character's face, hands holding the container of fake blood for all to see—spotlights the use of "masking" and pitches my assumed position. Is Bress performing an actor acting? Is that actor to be understood as Bress himself-and if so,  is this cheeky self-portrait of the artist? Or if a critic of painting, is this bumbling creep worth listening to? Whatever the answers, or the other questions Bress, true to form, deals (head-on) with the punning of face value.

Since receiving his MFA from UCLA in 2006, Bress has produced a number of self-starring, character-driven videos that with a deft sleight of handcraft spin this kind of viewer vertigo down a rabbit-hole dug somewhere between the worlds of Cindy Sherman and Pee Wee Herman. Walking around his studio, Bress discusses his work, his source materials, and the organic process by which he shoots and edits the videos, then re-shoots and re-edits over and over again  until the work feels complete. His studio is littered with art supplies, accessories and props: scenic flats lean next to wig stands that share a table top with power tools, rolls of tape and storage boxes.

He shows me three sets currently in use for the production of his second video, the 18-minute Because It's the Depression. The first set is an entrance to a mineshaft meticulously hand-drawn in graphite on cardboard; another, a stage painted in perspectival quilt patterns is a personalized twist on the standard video test patterns; and the third entails a massive galactic backdrop of blue paper cut-outs adhered to black cardboard and a black scrim. Bress's materials are often recycled or rescued. The cardboard for the mineshaft was found in the hallway of his building, as were a pair of plaster columns that stand nearby  The hundreds of paper cut-outs were painstakingly excised from a collection of thrift store books. So too are the characters collected. At one point in our visit, Bress plays an audio recording he made (clandestinely) while his dental hygienist,both hands in Bress's mouth, regaled the artist with an off-color story that ended in a joke involving an elephant and a naked man. (The punch line is yours to infer.) The artist tells me that initially, he was only  interested in studying the man's whine in order to imitate it later, but with this comedic material now in his possession, he may construct an entire character out of this recording. While Bress offhandedly sums up the origin and affect of his characters with the deceptively simple equation of "me plus them," he also says with a laugh that he always talks about his characters (their actions, personalities, and plotlines) in the third person, even when-in almost every sense-he is in fact talking about himself. (LEFT: BECAUSE IT'S THE DEPRESSION, 2009. COURTESY THE ARTIST AND CHERRY AND MARTIN)

There are still plenty of reveals left to wrestle, for Bress and his audience. As he and I screen the rough cut for Because It's the Depression, he cackles and comments on the shittiest acting ever" while watching himself play an astronaut who slurps coffee and asks his cardboard ship for a status report.  I ask Bress why he considers this version "rough" when all the elements (no matter how strange or deranged) seem to harmonize beautifully, even the so-called "shitty acting."  He then tells me about the many additions and revisions he is still simmering. He may shoot a sequence that will determine a different fate for one of his characters, add a sequence that plays with ideas of scale, paint the back-side of the spaceship so that it will be camouflaged against its background. With so much left to do, I compliment him on how calm and cool he seems so close to the show opening, He smiles and performs a big sigh of relief, "Good to know my acting's not as bad as I thought."

Brian Bress: The Royal Box runs from September 12–October 24. Cherry and Martin is located at 2712 S. La Cienega Boulevard, Los Angeles.