For fifty years, Fidel Castro, CIA code name “the Beard,” has been ashing his cigar in our laps. First, he deposed an ally of ours, Fulgencio Batista. Then he embarrassed our president by foiling an ultra-secret invasion. And, of course, he almost started World War III. But, worst of all, he just won’t die.

It’s no secret that, for decades, the US government has tried, and failed, to take out El Presidente. As the apocalyptic tensions of the Cold War have eased and Castro’s senescent regime winds down, our occasionally bizarre attempts to kill him have become cloak and dagger clichés, geopolitical gags from a nearly bygone era. The smart UK documentary 638 Ways to Kill Castro, released in the US on May 8th, lets us laugh at the more absurd death plots. But, in the end, director Dollan Cannell reminds us that our government’s Machiavellian interventions can be lethally serious.

Cannell’s style tastes of one part Michael Moore, one part Adam Curtis. The conversational narration, scholarly interviews, and newsreel outtakes give the film an engaging but journalistically rigorous depth that approaches Curtis’s brilliant Century of the Self or The Power of Nightmares. But Cannell throws cheeky found-footage into the mix, including clips of Cuban TV shows and snippets of old American gangster and spy movies. This irreverent collage effect puts the viewer in the same laughing-to-keep-from-crying mood as vintage Moore, but without the first-person subjectivity or political tendentiousness.

Much of the comedy derives from the weird schemes cooked up by Castro’s foes and their US backers. The “exploding cigar” is the most famously wacky of the plots, but compared to many of the others, it’s downright sane. One early bright idea was to spray an aerosol mist of LSD into a Cuban television station while “the Beard” was being interviewed. Others featured a poisoned diving suit, botulism pills, and mafia hit men. When the contrivances and wise guys failed, US spooks enlisted vengeful Cuban exiles like Antonio Veciana, a mild-mannered but fiercely anti-Castro accountant. But the results were more or less the same.

Veciana’s first of many attempts to kill Castro involved a bazooka in a hotel room. That’s right, a bazooka. A pistol wouldn’t do. A rifle was simply not grand enough. The only implement that could measure up to the rage and violence in Veciana’s heart was, apparently, a bazooka. As happened time and time again with Castro’s enemies though, Veciana’s own zealousness caused him to fail. When his hit men prepared to point the massive weapon out the window of their hotel, they realized its size and power would give their position away.

These kinds of farcical scenes, which would fit right into the Pink Panther series or even the Three Stooges, surely have a lot to do with Cannell’s cheekiness and irreverent approach. But the humor serves a separate, thematic purpose as well. By now, our government’s misadventures in Cuba have become wink-and-nod media yarns, kitschy narratives spiked with 100-proof realpolitik. Tom Clancy meets Forrest Gump. When George W. Bush looked for “those darn WMD’s” at the White House Correspondents’ Dinner several years ago, he was trying to shift his false pretext for the invasion of Iraq into the “exploding cigar” category of our history, a regrettable but ultimately well-intentioned blunder. Part of Cannell’s modus operandi is to engage, and ultimately rebuke, this American impulse to laugh away our morally suspect actions. And like a good cigar, the film lulls us into a pleasant, daydream-like reflection. Then it blows up in our face.

Orlando Bosch, 1970s

Posada Carriles, 1976

When George Herbert Walker Bush took over the CIA in 1976, our country’s efforts to kill Castro lost their farcical qualities. Instead of the accountant Veciana with his bazooka, we turned to genuine killers, like Dr. Orlando Bosch and Luis Posada Carriles. Hardliner blood merchants of the first order, these men did not bother with goofy stratagems like poisoned diving suits or exploding cigars. They killed their own people in Florida for trying to negotiate with Castro. They bombed hotels. And, in a horrible foretelling of tactics turned most powerfully against the United States, they downed a civilian airliner, Cubana Airlines’ flight number 455. Seventy-three people died in what was then the most violent act of terror in the Western Hemisphere. Cannell fades the screen to black as a visual stand-in for the carnage and, for most of the remainder of the film, the yucks die as well. The consequences of our country’s imperial machinations turn suddenly and nauseatingly real and, in the viewer, a hard pit of shame replaces the mirth.

Yet Cannell doesn’t choose sides in the back and forth between Castro and his enemies. While exiled activist Enrique Encinosa describes a public execution he saw on Cuban television as a child, Cannell cuts to file footage of an actual firing squad. The brain matter that sprays the wall behind the condemned man is real and, as Encinosa says, these disgusting spectacles were broadcast regularly as examples of what would happen to “anti-revolutionaries.” Enrique Ovares, one of the CIA’s first would-be assassins, weeps over all the lives he believes would have been saved if he had carried out his mission.

Posada Carriles and Bosch also speak candidly to Cannell. But their interviews are far from flattering. Bosch, a former medical doctor (like Osama Bin Laden’s number two, Ayman Al-Zawahiri), can barely contain his self-satisfaction as he neither denies nor confirms his role in the over fifty bombings to which he has been linked. “I don’t say yes or no,” he says with a grandfatherly gleam in his eye. He goes on to offer a patently Bin Laden-esque justification for his alleged acts: “In war, everything is valid.”

Cannell smartly avoids any direct comment on this smug declaration, but he makes clear that no important officials from the Cuban government were on the passenger manifest of Flight 455. The only victims remotely linked to Castro’s power structure were, of all things, the members of the national fencing team. Instead of hitting Cuba’s military or its decision makers, these self-righteous dolts butchered a bunch of athletes whose only weapons were intentionally blunted blades.

Cubana 455—as well as US-sponsored hotel bombings in Havana and the hundreds of assassination attempts on Castro—could easily be written off as regrettable episodes from our past, if not for the fact that the players involved remain not only at large but prominent in the public sphere. As head of the CIA, our former president, and the current president’s father, at the very least permitted the slaughter of innocents aboard the airliner and at the very worst, aided and abetted it. Florida Governor Jeb Bush first made a name for himself as campaign manager for future congresswoman, Ilena Ros-Lehtinen. Their winning slogan was “Free Orlando Bosch.”

Worst of all, Bosch and Posada Carriles are free and living in our country. Bosch spent time in jail for trying (with, you guessed it, a bazooka) to sink a Polish freighter heading to Cuba. But, in 1990, over the objections of advisors and the attorney general’s office, the first President Bush granted the doctor a pardon. In 2000, Posada Carriles was imprisoned in Panama for his role in the final, 638th attempt on Castro’s life. But shortly thereafter, he was mysteriously pardoned and wound up here in the United States. Just this month, a federal judge in El Paso dismissed immigration charges against him on an absurd technicality. The fact that he was only charged with minor “visa irregularities” is bad enough, but now he has even been cleared of those offenses.

Cannell repeatedly splices in clips from a hit Cuban television show based on Fidel Castro’s security detail. Far from fomenting discontent with “the Beard’s” rule, our meddling in Cuba has turned him into a primetime hero, an embattled underdog fending off a superpower’s aggression. Think of it as Cuba’s version of 24. Only their Jack Bauer doesn’t foil Muslim extremists. He nabs US-backed agents and saves Cuba from American-sponsored terrorism. Orlando Bosch’s pardon and Luis Posada Carriles’s exoneration are the latest acts in the drama.

Toward the end of the film, Cannell flashes our president’s now-famous declaration that, in the War on Terror, anyone harboring terrorists will be considered terrorists. The words are revealed as more than mere hypocrisy. In light of our actions in Cuba, the base cynicism of the rhetoric warps our national consciousness, creating the kind of free-floating mistrust of our leaders that spawns conspiracy theories and disenchants large swaths of our voting population. And this internal antipathy has done far more damage to our country than any bomb or bazooka ever could. Call it Castro’s revenge, an exploding Cohiba going off in our hearts.

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JB Powell is a contributing writer and the author of Republic: A Novel. Bottom image is of a memorial to the victims of the Cubana 455 bombing erected outside the courthouse in El Paso where Posada stood trial for visa irregularities last month.