Dear Dictator appropriates and then drains all subversion out of its punk and revolutionary trappings in favor of contrived, melodramatic pap.
There’s an argument to be made that the ensuing culture clash when an authoritarian island-nation strongman is forced to hole up with an angsty teenager in suburban America is fertile ground for incisive satire—you just won’t find anything to support that argument in Dear Dictator. This hapless, stultifying comedy—which also stars Katie Holmes as a romantically-desperate single mom and Seth Green as her foot-fetishist dentist boss—grasps at some modicum of watchability simply due to Michael Caine’s reassuring presence. The venerable actor’s poor decision to take the tonally inconsistent role of the exiled General Anton Vincent, a third-generation British-Caribbean tyrant with an affable demeanor despite his penchant for public executions, may not rank up there with skipping his first Oscar win to work on Jaws: The Revenge, but then again, with such a small budget, Dear Dictator isn’t going to buy him a new house either.
When wannabe-punk high-schooler Tatiana (Odeya Rush) is mildly bullied by the popular girls and can’t score with her prudish, evangelical bandmate (Jackson Beard), she thinks outside the box on an assignment from her teacher (Jason Biggs) to write a letter to someone she admires. Enamored with the fashionable regalia of the crumbling General Vincent regime, Tatiana strikes up an inexplicable correspondence with Caine’s besieged dictator, and when he’s overthrown via coup, Anton somehow turns up in her garage seeking refuge.
Tatiana’s punk credentials include wearing chunky combat boots and T-shirts with messages like “Piss Off” and “Don’t Look at Me” printed in block letters, along with her stated interest in seminal hardcore punk bands like Dead Kennedys and Black Flag. To establish her quirky rebelliousness, she’s got her relatively obscure cultural references down pat: she even disguises Anton in the wig and mustache she used for a Halloween costume of Dennis Hopper’s “Well-Dressed Man” getup from Blue Velvet. But as Dear Dictator unfurls, it becomes apparent she’s anything but anti-establishment, pining after a sanctimonious pretty boy and clearly influenced by the machinations of high school social hierarchy. That her interactions with the avuncular Anton only lead her to stage her own “coup d’éTatiana” to overthrow the “mean girls” (the film even directly name checks that culturally enduring 2004 film) diverts what could’ve been sociocultural satire into the most well-trod of high-school movie clichés.
When it’s not outright tone-deaf, Dear Dictator is at best toothless. Though Anton is an erstwhile Communist ruler, socialism versus capitalism is only given lip service—his lone speech to Tatiana about destructively voracious American consumerism feels shoehorned in, especially when he’s also involved in an obligatory shopping-spree montage. And the film’s fealty to teen melodrama touchstones is puzzling given the rich vein of commentary it leaves completely untapped. The clumsy subplot, involving Holmes’ pathetic, Daisy Dukes-sporting mom character getting fired by her philandering, toe-sucking boss, is played for laughs but comes off as simply ugly in the #MeToo era. Lacking any semblance of plausibility or, conversely, the satiric bite of effective farce, Dear Dictator appropriates and then drains all subversion out of its punk and revolutionary trappings in favor of contrived, melodramatic pap.