Filmed during the very real tour of his 2008 film Woodpecker, writer-director Alex Karpovsky stars in Red Flag as heartbroken, recently-dumped filmmaker Alex Karpovsky. In need of money to ameliorate his debt, Alex travels through six Southern states to introduce and moderate Q&A's for his film, explaining to his brother that this mini-journey will be "a good opportunity to reflect on things and gain perspective." Alex believes this even less than the audience is expected to believe him, as only a second later he's on the phone, calling everyone in his phone book and inviting them on the tour. Without any takers, Alex is forced to spend most of his next two weeks trapped in a dinky rental car or seedy motel, grappling toward modes of distraction and further developing self-destructive compulsions.
Alex finds short-term relief in River (Jennifer Prediger), a bespectacled, sycophantic young woman who attends a screening; she compliments him, drawing a parallel to Woodpecker by calling Alex a "charismatic megafauna" (Prediger's delivery perfectly nails obnoxious Q&A lingo, as River "doesn't have a question," but she "just felt she had to say that"), and it's not long before they're having awkward, aggressive sex. Alex delivers a post-coital, passive dismissal of her, after which he heads to the next location, where his charmingly affable and hirsute quasi-friend, Henry (Onur Tukel), has agreed to join him on the tour. Alex doesn't correct Henry when Henry implies that Alex and his ex-girlfriend of nearly five years, Rachel (Caroline White), are still together, and Alex quietly becomes more and more obsessed with the idea of winning Rachel back.
Karpovsky has fun with Alex's inability to communicate with Rachel over the phone, amusingly mangling the speech he's prepared, ironically referencing a constellation when he can't cobble together his ideas to create one coherent, genuine thought. Snippets of Karpovsky's unique docu-drama Woodpecker appear while Alex presents the film to mostly old audiences, and the same theme of redemption is repeated multiple times to highlight Alex's unconscious intent to force an epiphany on himself ("When you're called down and out. When you're called extinct, you get a second chance" is just one of the on-the-nose soundbites).
The most surprising aspect of Red Flag, however, is how it abandons its obvious meta elements and unfolds as a straightforward road-trip flick, opting for an exhibition of self-loathing rather than self-reflexivity. The film is reminiscent of the work of monolithic Jewish artists (namely, Woody Allen, Albert Brooks, and Larry David) without approaching their heights of thorny social awareness; the result is a teasing, gag-filled experiment—more a trifling specimen of self-analysis through exaggeration rather than a bold undertaking of artistic vision. Kaprovsky exhibited his ability to play with form in the more accomplished, Ross McElwee-like The Hole Story, but with Red Flag he seems determined to play down his conceit.
Karpovsky punctuates many moments with goofball, slapstick humor (e.g. hurting his back while packing the car as he moves out of his ex-girlfriend's house, getting hit in the face with beads at a parade), which is meant to disarm and amuse, but instead comes off as disingenuous affectation. The facile physical comedy robs Red Flag of the wry bitterness that Karpovsky the writer-director occasionally captures via Karpovsky the character's acute ability to lie to himself. In Alex's introduction to a classroom of ostensibly stoned teenagers, Karpovsky allows his bitterness about life to cannibalize his explanation of Woodpecker, and you wish that vituperation had bled into a majority of his directorial decisions in Red Flag, which is far too preoccupied with using comedy to defang truths rather than inform them.