Alex is having a rough time. His inflated ego and crippling fear of commitment cost him his relationship with his longtime girlfriend who, after five years of disappointments, finally got sick of his shit and kicked him to the curb. Desperate to avoid the loneliness of the open road, Alex tries to recruit a friend to join him on his film tour, but he soon finds out that most of his friends aren't too happy with him either. With some series debt to take care of, Alex can't afford to cancel the tour, so he convinces himself to try to make the best of his solo journey.
But he's not alone for long. Alex's old friend Henry (Onur Tukel), a spacey children's book illustrator, is the first to join him on the tour. Things seem to be looking up until Alex decides to rebound with a tenacious fan (Jennifer Prediger) who, after following him from city to city, forces her way into his life by jumping into a crazy fast relationship with Henry, adding to Alex's misery. Eventually Alex's ex-girlfriend Rachel (Catherine White) joins the group after he begs her to fly out to New Orleans as a poorly timed last-ditch effort to save his failed relationship. The inevitable awkwardness that arises from placing four people dealing with their own individual existential crises in a single car together creates great space for comedic opportunities.
Karpovsky's owes a lot of RED FLAG's success to his stellar supporting cast. Tukel's charisma is irresistible, and his portrayal of Henry--incredibly sweet and totally willing to risk everything in pursuit of the love of his life--is a much-needed counterbalance to Alex's intense cynicism. Jennifer Prediger is absolutely perfect as Alex's gorgeous-but-creepy stalker fan, and Caroline White nails the pissed off ex-girlfriend role.
Karpovsky seems to have no qualms about portraying himself as a total screw-up, a talented bullshitter who'd do anything to feel a little less fucked up inside, and can see the humor in his own misery. Alex's misadventures are so absurd that you can't help but laugh at his self-induced suffering and hope he somehow finds his way. (One of my favorite scenes is when his mother calls him up at one of the many crappy hotels he crashes at and yells at him in Russian for being such a wuss. "I would've dumped your father if he made me wait so long too!") It's Karpovsky's willingness to not paint himself as a sensitive genius, misunderstood by the world, that makes RED FLAG such a compelling and amusing film.