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It's Cuban

 It's Cuban
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It's Cuban
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In American media, Cuban cigars, which were banned in the United States after Fidel Castro seized Cuba in 1959 (an embargo that was temporarily lifted in 2015, but mostly resumed in 2017), have generally been considered items that cannot be acquired without the right connections and/or money. Therefore for a character to offer or have a Cuban cigar is usually used as shorthand for having one or both. Because of the reasons why Cuban cigars had that status in the first place, there is usually also a sense of nefariousness added to whoever has or offers the cigars in question.
Sometimes a case of Creator Provincialism and/or Eagleland Osmosis, when a character boasts about their cigars coming from Cuba in works set outside the U.S., where there are no trade embargoes against Cuba to restrict their availability in the first place.
The current political situation is not quite a Trope Breaker just yet, but it does greatly diminish the significance of a character possessing Cuban cigars, since they're no longer considered contraband in the US, and all that's needed to get them is a passport. Do note, though, that while restrictions against importation have been relaxed to the point that quantities can be purchased from outside the US and legally brought into the country, the cigars are for personal use only and are not legal to resell. They still cannot be bought wholesale from Cuba and resold by retailers in the U.S., so until such a time that the trade embargo is fully lifted, calling your local tobacconist to ask for Cuban cigars will only get you an annoyed tobacconist.
See also Good Smoking, Evil Smoking and Made in Country X.
Note: While this trope usually refers to cigars, it can also apply to Cuban rum, especially Havana Club.
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Zig-zagged in Super Troopers 2. Cuban cigars are among the contraband the troopers find and it's never pointed out that the embargo against them does not apply in Canada (the setting), but the cigars are intended for smuggling into the U.S., where resale is still illegal.
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In The World Is Not Enough, Bond meets with a shady Swiss banker in Bilbao, Spain, and the banker's assistant offers him a Cuban cigar in a silvery holster. After fighting his way out and coming back to London, Bond offers the cigar to Moneypenny... who promptly throws it in her trash can.
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It's Cuban
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Heroes Reborn: Fantastic Four: In Issue 7, Johnny brings a hospitalized Ben a Montecristo cigar "straight from Havana" as a nice gesture.
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In King of the Hill one episode had Hank being offered a Cuban cigar. Being the strict rule-follower he is, he breaks it in half and says "you might not have known but this is Cuban, I'll just destroy it for you."
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Labyrinths of Echo: In the second book, after becoming a successful magician detective, Max accidentally discovers his former supervisorsnote Middle managers in a small news outlet. smoke Sumatra cigars despite claiming them to be Havana. Considering, how little the price differs in Russia and Germany, this makes them real cheapskates.
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James Bond:
In The World Is Not Enough, Bond meets with a shady Swiss banker in Bilbao, Spain, and the banker's assistant offers him a Cuban cigar in a silvery holster. After fighting his way out and coming back to London, Bond offers the cigar to Moneypenny... who promptly throws it in her trash can.
In Die Another Day, Bond goes to Cuba to find a sleeper agent who happens to have a cigar factory as his cover. Bond asks for "Delectados", to which he's answered that "they don't make them anymore". It's actually the sleeper agent's Code Name.
The "Delectados" get a Mythology Gag in No Time to Die, where Bond finds the remains of a cigar of that very brand at his house in Jamaica. It turns out the cigar was smoked by his CIA friend Felix Leiter, who appropriately recruits him for a mission in Cuba and tells him to bring back a cigar for him. Paloma finds one in a car used by a SPECTRE goon and gives it to Bond to take back. Tragically Felix dies without having a chance to enjoy it.
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In The Cleaning Lady, Arman has sufficient connections that he's able to procure whole boxes of Cuban cigars. He gives them to favored customers as a bonus to help sell his regular merchandise, sometimes having his wife Nadia smoke one to demonstrate their supposed potency.
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The boxes of cigars occasionally found in BioShock are labeled "Habana Especial". In this case, the embargo being skirted is Rapture's own, having banned travel to the surface (and, by extension, acquiring goods from there) since its founding. Though given Rapture's lax attitude towards business ethics, it's just as likely that they're not even genuine.
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Played for laughs several times in Seinfeld. In one instance, Kramer gets a box of Cuban cigars from George's fiance's father, which he accidentally uses to burn down her father's cabin. Another time, Kramer hatches a scheme to bring in Cuban refugees to roll Cuban cigars for him in America, but they turn out to be Dominicans and thus inferior cigar rollers. A third episode has a man named Todd Gack sell Jerry a box of Cuban cigars for 300 dollars. They turn out to be from Peru, and Jerry finds it impossible to get his money back.
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In Far Cry 3, Hoyt Volker offers Jason Brody a Cohiba after Jason- undercover as one of his privateers- presents him with a list of traitors and photos that Hoyt has to get rid of. When Jason states that he doesn't smoke, Hoyt remarks that he needn't worry about getting cancer, because on the Rook Islands, "cancer won't be what kills you".
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Invoked in an episode of Hogan's Heroes. Klink tries to butter up the visiting General Burkhalter by offering him a tray of delicacies from across German-occupied Europe. Burkhalter takes one of Klink's cigars, sniffs it, and sours in disgust. Klink apologizes and explains that he could only get German cigars, and Burkhalter muses that they should've invaded Cuba.
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Parodied in Futurama with Zuban cigars. Likely from the planet Zuban 5, mentioned in another episode.
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In KGB, which is set in the notoriously destitute Soviet Union, a character's possession of Cuban cigars is one of many clues that he's corrupt. This in spite of how the U.S.S.R. was a close ally of Cuba and never imposed any trade embargo against them; Cuban cigars were the kind of luxury a Soviet bigwig would be most likely to possess.
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Spider-Man: In The Spectacular Spider-Man #21, mob boss Kingpin invites himself to a superhero poker game for fun, bearing a Briefcase Full of Money to sweeten the pot. If the heroes win, they can donate it to a charity. If Kingpin wins, he'll buy a boat to rub their loss in their faces, as well as a Cuban cigar:
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Father of the Bride (2022): Just before the wedding, Billy scoffs at Hernan ordering boxes of Mexican cigars. After it, he busts out a couple of Cuban cigars and shares one with his new consuegro, clarifying that these cigars were pre-Castro.
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In Metal Gear Solid 3: Snake Eater, Major Zero offers a hospitalized Snake a Cuban cigar.
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Subverted in The Punisher (2004). Saint tells Mike, one of the Toro criminal brothers to not touch the Cubans as Mike walks towards his cigar collection and helps himself to one. When Mike takes his leave, he indignantly notes that the cigar was Honduran, and tosses it on the floor.
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CSI: In "Forever", the CSI team finds tobacco shreds in a horse's mouth. Identifying the tobacco as coming from a Cuban cigar, they start looking for a suspect who might have access to (illegal) Cuban cigars. This leads them to a former concierge from a top-end hotel.
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In the first season of JAG Harm and Meg go to Cuba and enjoy local cigars. Subsequently, Harm is shown enjoying Cubanos in the States for several seasonsnote the character eventually quit on screen because David James Elliott quit smoking in real life, implying he either smuggled a large stash back with him or he found a source after acquiring a taste for them.
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Dr. Strangelove touches on the politics behind the embargo in a scene where Soviet Ambassador DeSadesky asks for "Havana cigars". When an American general offers him Jamaican cigars, he sneers that he "does not support the work of imperialist stooges", to which the general responds "Only Commie stooges, huh?"
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In the megacrossover event Underworld Unleashed, the Joker sold his soul to Neron for a box of cigars. When mocked by Circe for selling his soul at such a low price, he defended himself by stating they were Cuban.
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Superman '78: After Brainiac III carts Superman away in Issue 3, evil billionaire Lex Luthor offers Lois a Cuban cigar, and comments that it's her loss if she's too distracted to have one.
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In How I Met Your Mother when Ted gets upset by Barney smoking a cigar in his car, Barney mentions that it is a Cuban cigar and that people pay to make their cars smell like them.
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Black Hawk Down has captured arms dealer Osman Ali Atto offer General Garrison a Cuban cigar. Garrison shows he has his own, which Atto dismisses as a knock-off in a subtle commentary over which side has a clearer view of the conflict.
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The Sopranos: In "A Hit is a Hit" Tony gifts his next-door neighbor Bruce Cusamano some premium Cuban cigars. Bruce marvels at them, and throughout the conversation, it's implied Tony managed to procure them because he's a mafioso.
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In Die Another Day, Bond goes to Cuba to find a sleeper agent who happens to have a cigar factory as his cover. Bond asks for "Delectados", to which he's answered that "they don't make them anymore". It's actually the sleeper agent's Code Name.
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The following is a list of statements referring to the current page from other pages.

 It's Cuban
processingCategory2
The Smoking Section
 Superman '78 (Comic Book) / int_37707f7a
type
It's Cuban
 The Kingpin (Comic Book) / int_37707f7a
type
It's Cuban
 The Spectacular Spider-Man (Comic Book) / int_37707f7a
type
It's Cuban
 Black Hawk Down / int_37707f7a
type
It's Cuban
 No Time to Die / int_37707f7a
type
It's Cuban
 Scarface (1983) / int_37707f7a
type
It's Cuban
 The Family Man / int_37707f7a
type
It's Cuban
 The Punisher (2004) / int_37707f7a
type
It's Cuban
 Wall Street / int_37707f7a
type
It's Cuban
 Labyrinths of Echo / int_37707f7a
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It's Cuban
 How I Met Your Mother / int_37707f7a
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It's Cuban
 The Cleaning Lady / int_37707f7a
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It's Cuban
 KGB (Video Game) / int_37707f7a
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It's Cuban
 The 3 Little Pigs: The Movie / int_37707f7a
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It's Cuban