An audacious conceit in search of a bolder movie, “Dear Dictator” has 85-year-old Michael Caine as a Latin island tyrant whose overthrow improbably lands him in the garage of a suburban American teen. That casting and concept alone have a certain goofy appeal that makes writing-directing duo Lisa Addario and Joe Syracuse’s third feature a pleasant watch for a while. But instead of heading in the logical directions of farce or black comedy, it ultimately goes warm-and-fuzzy, making for possibly the most curiously inoffensive movie about a fictive despot ever. There are things to like here, but there’s also something more than a tad queasy-making about a film whose key figure admits to political torture and executions — yet which viewers are likely to shrug off with “Well that was kinda cute.”
Doing her best not to be cute is Tatiana Mills (Odeya Rush), a consummately disgruntled high-schooler who listens to vintage punk bands and repels all social contact beyond incongruously ultra-Christian bestie Denny (Jackson Beard). She’s fatherless, her flaky single mom Darlene (Katie Holmes) having conceived her at the start of a lifelong pursuit of Mr. Wrong. Currently holding that position is dentist (and foot fetishist) Charles (the always-welcome Seth Green), who is an especially apt choice, as he’s married — and hygienist Darlene’s boss.
Social studies teacher Mr. Spines (Jason Biggs) tasks students with writing a letter to “a luminary who inspires you.” Pushing rebel-girl cred a bit into red flag territory, Tatiana writes internationally deplored dictator Gen. Anton Vincent (Caine), because in her glibly nihilistic view, he’s “cool.” To her amazement, he writes back —perhaps because he’s estranged from his own daughter, perhaps because he needs distraction from his tottering regime. When actual, U.S.-backed rebel forces storm his palace, he’s forced to flee, and for lack of other options winds up at Chez Mills.
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To a point, “Dear Dictator” is a likable, promising mash-up of “Lady Bird”-type teen misfit comedy and “Children of the Revolution”-type impudent political satire. Never mind that the ever-charming Caine is bizarrely miscast — what’s that London accent doing in a third-generation Latin martinet’s mouth? — or that Anton seems terribly nice, even harmless, for someone guilty of crimes against humanity. There’s a certain esprit to his training Tatiana in Machiavellian techniques so she can win her own “class struggle” (against the school’s mean-girl triumvirate), and to the fact that while waiting to launch his own counter-counterrevolution back home, he proves rather handy around the house.
But “Dear Dictator” doesn’t do as much as one would like with the good ideas it has, and then it has increasingly bad ideas — like waterboarding as a slapstick gag.
It’s not just that the creators don’t have the chutzpah to take their own concept far enough. It’s that they betray that concept by embracing a very conventional sentimentality in which the eccentric but nice old man teaches mom and daughter to be better versions of themselves. Surely it wasn’t their intention, but Addario and Syracuse really do wind up unironically amplifying the wisdom of “Oh, Hitler wasn’t so bad — after all, he liked dogs and babies!” A different movie might’ve pulled even that off, albeit in subversive terms. But “Dictator” is less subversive than the ancient likes of “Eating Raoul” or “Death to Smoochy,” neither of which dared name-drop the Khmer Rouge.
Rush (“Lady Bird”) is an impressively versatile young actress. Holmes is quite good in a role that feels like a particularly happy fit — arguably she hasn’t been this relaxed and in-character since “Pieces of April” 15 years ago. Green and Biggs seem very game for better comic material than ever arrives for them here. Caine is a treasure, but this isn’t one of his best roles, even if it’s one of his largest in recent years.
Pleasant enough to watch, even innocuous, “Dear Dictator” is something that gets worse the more you think about it. That reaction is forestalled by smooth tech/design contributions, the one inspired element being music supervisor Asif Ahmed’s mixtape soundtrack of prime vintage punk-pop tracks by Circle Jerks, the Dead Milkmen, Operation Ivy, Bikini Kill, Team Dresch and more.