"In my mind it sounded so different from the way it came out. It sounded hilarious. But it came out so not hilarious."

Way back in 2009, when "mumblecore" was still a word you might say without being eye-rolled out of the room, Alex Karpovsky's first acting gig found him stumbling though the line above, which, odds are, will aptly describe his career for as long as he chooses to continue it. The film in which it appears, Andrew Bujaski's Beeswax, was the first and last time Karpovsky, who you probably know better as Ray from HBO's Girls, would find himself playing the role of the "nice guy."

The New York-based actor/director/writer will be at the Castro Theatre this Saturday for a screening of his latest film, Red Flag, at the San Francisco Jewish Film Festival. Red Flag and its sister film, Rubberneck, which were made at roughly the same time and released simultaneously on-demand and in (very select) theaters back in February, have been steadily gaining low-key acclaim since their release. Though Red Flag also plays Sunday at Grand Lake Theatre in Oakland, Karpovsky will be in and out before it shows again, a hazard of a ravenous promotion and production schedule that includes a new Cohen brothers film, his own work, and (of course) his role as the 30-something lost boy in the HBO hit series.

When we speak over the phone a few days before his visit, he has a confession to make: "I enjoy playing the jerk, I do. It's fun for me to do because I've found there's only a handful of ways you can even portray a straight man or a nice guy, but there are an infinite number of ways to play a jerk and that versatility, that spectrum, is something that I'm interested in."

Is Karpovsky really as much of a misanthrope as the characters he plays? Our conversation seems to suggest the opposite, though he admits that most of his characters are "negotiating with a lot of conflict and dissonance on a very daily level." His two most recent roles are certainly riddled with dissonance. In Rubberneck, he plays an accidental stalker whose one-weekend stand with a coworker escalates to a dangerous and legitimately creepy obsession, and Red Flag’s quasi-autobiographical film tour (for his real-life first film, Woodpecker) finds him floundering after his girlfriend breaks it off.

If there’s a whiff of Woody Allen coming through, it hasn’t gone unnoticed–the catalog for SFJFF mentions the Manhattan director not once but twice in the notes for Red Flag. Karpovsky is fated to suffer, and benefit, from the shorthand for a long time to come, and although he namechecks Allen, Larry David, and Louis CK as inspiration, there's a certain signature blend of arrogance, modesty, and good-natured humor that distinguishes him from these neurotic self-destroyers. He may have bigger fish to fry: Red Flag, in which Karpovsky’s character plays a jacked-up version of himself á la Woody, has been favorably compared to Michael Winterbottom's The Trip, which he considers a "huge influence" for his own entry to the buddies-on-a-road-trip-into-darkness genre. "I get a kick when people play amplified versions of themselves," he says with a calculated sense of understatement.

Later in our conversation I mention that I'd always assumed that Girls was produced as a collaboration and he's similarly deflective, pinning the praise to the show’s creator Lena Duhnam: "I think that sentiment is a testament to just how perceptive Lena is and how good of a writer she is." When I ask about his role in the Cohen brothers' Inside Llewyn Davis, in which he appears along with fellow Girls guy Adam Driver, it's apparent that his modesty always comes tempered with an equal dose of sarcasm. Though he's humbled by the opportunity to work with the Cohens, whom he calls "two of his favorite filmmakers working today," his schedule has been so busy he hasn't yet seen their film. "I know I'm not cut out, that's all I know."

Red Flag plays at The Castro Theatre this Saturday, July 27th at 7:30pm as part of the San Francisco Jewish Film Festival.