An Ambassador's job is two-fold: to maintain healthy relationships with the country he is sent to, and to be well-versed in the customs and minutiae of their culture. The Ass in Ambassador forgets this. He is rude, makes no attempt to do as the Romans do, and shows little sign of being friendly (or even respectful) at all. Even attempts by his staff at Tactful Translation rarely undo the harm he causes. As a result the other ambassadors or representatives are forced to bend over backwards and take every insult or unreasonable request, because if they ever decide to resist for one moment, the ambassador will be immediately insulted and threaten to break all ties.
A variant on this is an ambassador who is friendly, but perhaps too much. They are eager to learn the customs of the new culture and are constantly asking questions. While not mean, they seemed to have skipped the chapter that teaches about personal space, privacy, and uncomfortable questions.
See Diplomatic Impunity for when ambassadors are outright criminals. A subtrope of Poor Communication Kills. When the Ambassador is trying to be good, but his government's spies are doing everything he says they wouldn't do, it's Right Hand Versus Left Hand. Contrast (hopefully) Ambadassador.
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Sinbad shows up as an ambassador in Fables; while he ends up being basically reasonable he does start off insisting on being allowed to keep his slaves and refusing to speak with women. A more severe example is Sinbad's adviser, who tries to kill everyone due to the differences in culture.
The novel The Ugly American, which has a number of characters who act like this, including an ambassador. Not, however, the title character, who's called that because of his appearance, not his actions.
One book in the 'Tom Clancy's Net Force series subverts this. The antics of the usual types at an embassy are used as cover by the intelligence agents there. A covert intelligence agent's dearest wish is to be dismissed by opposing counter-intelligence as a drunken fratboy. So the trick at an embassy party is determining who's a real drunken lout, and who is just pretending to be one.
In the Discworld books, Vetinari keeps using Vimes as a diplomat knowing full well that Vimes doesn't care for niceties. Tends to be the first kind but manages not to be horrible at it. For example, at a meeting with the Istanzian ambassador Vimes indicated that further military indiscretions across the Slipnir River (notably not toward Ankh-Mopork itself) would result in the ambassador, as Vetinari quoted, 'going home in an ambulance'. After which the forces pulled back so far they were almost in the next country. Vimes did apologize to Vetinari, who claimed Vimes's opinion complied only with the general thrust of his own view but had at least been effective, claiming it had been a very long day and all, but Vetinari says plain speak confuses the diplomatic corps, which is as he likes it. Or there's the time he's sent as ambassador to a very fundamentalist Uberwaldian Dwarf kingdom, taking as his attaches a hulking unlicensedtroll and a visibly female dwarf, both deliberately chosen to raise hackles. This is the rough equivalent of visiting Iran with a Mossad agent and a transvestite. In the same mission Vimes also manages to (unintentionally) insult a dwarven bigwig through his somewhat limited grasp of the Dwarven language, and (again, unintentionally) alienate parts of the dwarven religious caste by jokingly appending "blackboard monitor" to his already overly long list of titles (fundamentalist dwarves believe erasing words is sin).
Most Terran ambassadors in Keith Laumer's Retief stories are pompous, ignorant of the societies to which they're accredited, and overbearing or obsequious depending on whether you're weaker than or equal to/more powerful than they are. In one historical preface, Laumer uses phrases like "fearlessly cowardly, uncompromisingly venal, and deviously sincere" to describe them.
And then in some cases, Retief arguably took this role in order to get something done while his superiors are too busy trying to not upset the people in power in any way to do their jobs. These incidents were intentional, deliberately calculated, and got results (for which his superiors promptly took credit).
It is worth mentioning Laumer was a member of the diplomatic corps for several years. Most of the stories are supposed to have some reality behind them...
WhatMaltsev and the Persian government portray Griboyedov to be at the end of The Death of the Vazir Mukhtar. They are not entirely incorrect - he has allowed himself some shockingly reckless behavior on both trips to Persia, though that was more of a calculated gambit than a product of stupidity or ignorance. He has allowed himself to be entirely polite and helpful in other, less seemingly critical matters.
In Starfighters of Adumar, Wedge Antilles maneuvers around this trope. He's sent to Adumar to try and bring it into the New Republic purely because Adumarians love great pilots, and he's the best. But he will not kill the terribly unskilled Adumari pilots in practice combat. He outright refuses. That makes his diplomatic liaison bring this trope up; by not respecting their traditions, he's making the New Republic look bad, and the Imperial ambassador looks better. Wedge still refuses. He hates a lot of aspects of this society, like their bloodthirstiness, their readiness to kill each other, and their concept of honor; he'll respect their other traditions, but not these. It does work out better in the end.
The real ass in the book is the liaison himself. After Wedge refuses to play the Adumari's game, he tries to have them killed by telling the Cartann ruler that Wedge, Tycho, Janson, and Hobbie want to die in order to restore some lost honor.
Young Jedi Knights Book 4 "Lightsabers" has Ambassador Yfra, who tries to have Tenel Ka and her grandmother Ta'a Chume assassinated several times. With Tenel Ka's parents gone from the planet she would have no problem taking power, and she assumes power when she mistakenly believes she's succeeded.
Justified in Romance of the Three Kingdoms; Cao Cao sends Mi Heng as an ambassador to Liu Biao because he's an ass: Cao Cao wants Mi Heng dead for insulting him, but doesn't want to sully his reputation by killing as reputable of a scholar as Mi Heng was. Cao Cao figures that Mi Heng will do something that will get him executed by Liu Biao while acting as ambassador. Mi Heng quickly manages to offend Liu Biao, but he responds by sending him off to one of his subordinates, to show he understood Cao Cao's intentions. The subordinate ended up executing Heng over the following insult:
Mi Heng: You are like a god in a temple: You sit still and receive sacrifice, but the lack of intelligence is pitiful.
Justified in that he didn’t actually need to establish good relations with the heroes—Sauron fully intended to annihilate them all anyways.
The Star Trek Novel Verse has a few of these (this being Star Trek; see below). Among them is Ambassador K'mtok of the Klingon Empire. He's introduced in Star Trek: A Time to... as a particularly hawkish diplomat, appointed as a replacement to the far more reasonable Ambassador Lantar. When Federation President Zife went over Lantar's head to talk directly with Klingon Chancellor Martok, Martok's political rivals on the Klingon High Council used the opportunity to force their man into the ambassadorship, claiming Lantar had been proven ineffective. However, K'mtok gets better over time, showing President Bacco some degree of genuine respect in Star Trek: Articles of the Federation and Star Trek: Destiny. By this point, Ambassador Tezrene of the Tholian Assembly has taken over as the biggest Ass In Ambassador.
In Star Trek Vanguard, set over a century before K'mtok and Tezrene's time, the Klingon and Tholian diplomats also love being this (especially the Klingons). Federation Ambassador Jetanien sometimes acts this way too, partly to throw it back in the Klingons' faces. Funnily enough, he and Klingon Ambassador Lugok end up in Vitriolic Best Buds territory.
The High Ridge administration, and in particular Descroix, who was the Foreign Secretary, handled the diplomatic relations with Erewehon so badly that they switched sides, and it was mainly their refusal to negotiate a peace with Haven that created a situation in which Eloise Pritchart felt justified in resuming hostilities against Manticore. Several characters note that they couldn't have done a better job of alienating Manticore's allies if they'd tried.
Star Trek is in love with this trope, especially if the planet has a hat. They will go around rudely asking random questions, or sometimes just throw the hat in the face of the crew and expect them to deal with this. As often as not, however, they have legitimate reasons behind their behavior.
This goes all the way back to Star Trek: The Original Series, which still probably features more of them than any other series. It's no wonder there was a Space Cold War with the Klingons going on in that era. Seriously, you could populate a friggin' starship with all the dickish, snotty, and sometimes suicidally idiotic Federation officials the Enterprise had to ferry around.
High Commissioner Ferris from "The Galileo Seven" was the earliest example. He had a legitimate reason (the Enterprise had to deliver urgently-needed medical supplies) but that still didn't stop him from being a total Jerk Ass and even seeming to relish news of the shuttle and all hands being lost.
There's Robert Fox from "A Taste of Armageddon," who was also completely incompetent at his job and seemed to have a total lack of intuition. If it hadn't been for Scotty, the Enterprise would have been blown to smithereens. In the end, he's left behind to help negotiate the peace treaty between two planets that have been warring for centuries! Yeah, good luck with that...
In justice to Fox the subtext is his mistake was trying to usurp the duties of a Starfleet officer. Once he focuses on his proper job, diplomacy, he becomes effective and even likeable.
In the episode "Journey to Babel," we find out that when you put a group of Ass In Ambassadors on a starship together, they start killing each other.
One of these ambassadors is none other than Spock's father, Sarek, and the two have been estranged for many years - it turns out that Sarek was even an Ass In Ambassador to his own son.
Star Trek: The Next Generation: Counselor Troi's mother, Lwaxana Troi, is the Federation ambassador to Betazed. How she acquired the post is anyone's guess. She's openly disdainful of all non-Betazeds, hates space travel, and is insanely chauvinistic to the point of objectifying every man she encounters. To say nothing of casually endangering the Enterprise in order to bed Captain Picard, who's desperate just be rid of her.
In "Liaisons," we meet one ambassador who fits type one to a tee, along with a second brusque one, and a third who is a bit obsessed with sweets and desserts once he learns of them. Each of them, however, was specifically attempting to understand the human species, and the behavior of the first two is different than their actual meanings. The second apologizes for their behavior, aware he may have crossed a cultural line.
While there are technically no Ambassadors in "Code of Honor", the episodes represents the spirit of this trope very well. A planet of barely civilized aliens has a vaccine for a deadly illness happening in the Federation. And so the Enterprise crew put up with tons of crap from them, including the kidnap of Chief of Security Tasha Yar, by the leader of these people. Picard even mentions that this qualifies as an act of war, but that doesn't mean he'll attempt a rescue.
Star Trek: Deep Space Nine: In one episode, we meet a race whose hat is Games. Upon traveling through a wormhole and meeting their first alien species, the ambassadors... decide to go to Quarks. After proclaiming that all of his games are too dull (apparently, they're not a fan of most gambling games, but rather board games), they start their own game, which puts all but one player in hazardous situations inside the game, while the other makes decisions as to what they should do. It isn't until the end that we are told this is all harmless.
In another episode, one of the subplots involves Dr. Bashir getting stuck escorting a group of Federation ambassadors on the way to the Gamma Quadrant around the station; they are so annoying that he proclaims them "the ambassadors of unhappy."
The infamously-bad episode "A Night in Sickbay" has both sides acting like this. Archer brings his dog down to a planet known to be populated by a species that's very hung up on tradition and ritual, and the dog proceeds to pee on a sacred tree, greatly offending the aliens. He then spends the rest of the episode behaving like a petulant child over both the fact that the aliens got pissed off and the fact that his dog contracted a disease on the surface of the planet — and only gets worse when the aliens demand an elaborate ritual of apology.
Ambassador Soval of Vulcan is a bitch until the fourth season. It takes Admiral Forrest dying while saving his life to finally defrost him.
The US Ambassador to Bulgaria, Ken Cochren, slept with the Prime Minister's daughter. The President knew Mrs. Cochren. Ken ended up very fired. Cochren also is a jerk to Charlie about the fact that the ambassador had been a member of a all-white club, which leads to a very funny moment with the president.
The Iranian Ambassador to the US was also a jerk.
Bartlet also considers the Indian ambassador this, although it appears to be more personal dislike rather than any inherent failings on the ambassador's part. The Pakistani ambassador also has some strained meetings with the President in the episode they both appear, although that's probably more to do with the increasing and potentially war-creating tensions between India and Pakistan at the time than ineptness on his part.
Another episode made a small subplot out of the relatively minor but very real problem of UN diplomats parking willy-nilly in New York and relying on their immunity to get out of paying the tickets. The diplomats complain to the Secretary-General, who wants to complain to the president, except that Leo asks Charlie to make sure he doesn't take the call because he knows it'll piss him off. The Secretary-General manages to get through at the end of the episode, by which time Bartlet is in no mood.
Narn ambassador G'Kar, especially during the Pilot Movie and first season, was a giant Smug Snake very good at stepping on pretty much everyone's toes (though especially Londo's, due to the Narn/Centauri feud). He mellows down significantly after the events of the first season and ends up becoming a Messianic Archetype to his people.
Vorlon ambassador Kosh, a Sufficiently Advanced Alien who barely attends diplomatic functions at all and when he does appear speaks entirely in Cryptic Conversation, Koans and Mathematician's Answer. He ends up becoming The Mentor to Sheridan, but the rest of the station still find him very distant at best. We later learn he is one of the most alien-friendly Vorlons in existence, and his replacement Kosh II (Ulkesh) is downright malicious and view the younger races as flawed tools at best.
As an inversion, Vir Cotto makes an honest attempt in being a proper ambassador to Minbar, but to his dismay, Londo insists on "correcting" his report to the Royal Court. It turns out that the Royal Court is tired of sycophants and would have preferred Vir's original version.
In the episode "Acts of Sacrifice," Ivanova had to deal with the Lumati ambassador. A Social Darwinist elitist race believing in "survival of the fittest", the ambassador wouldn't even talk to Ivanova, letting his attaché speak for him, until he is certain that humans are worthy, which happens when he misinterprets Down Below as a human scheme to separate the inferior members of their race from the rest of them. This leads to one of B5's Crowning Moments of Funny/Awkward: Awkward, because the Lumati seal treaties by having sex; funny, because of how Ivanova gets out of it.
We also meet several Earthdome diplomats over the course of the series, usually sent from homeworld to negotiate some background deal or another. Almost all of them are short-sighted jerks, except for a kind old man who turned out to be The Chamberlain.
Sir Jonathan Tutt, British Ambassador to the United Nations, in In the Loop. His over-friendliness with spin doctor Malcolm Tucker just comes across as really inept flirting.
Cory in the House: Raum Paroom, the Bahavian ambassador to the United States, and father of the titular character's best friend/love interest, smugly asserts the superiority of his own culture. He also forces his daughter to stand out like a sore thumb and restricts her relationships in the name of maintaining her cultural identity and not getting too assimilated in American culture. He mellows out somewhat, but still has his moments.
One episode of Night Court features an ambassador from a small nation next to Switzerland who abuses his powers because the US needs them to spy on the Swiss. Of course, part of the reason that he is so irritable is that his people have nothing better to do than watch the Swiss.
John Adams, as portrayed in John Adams. "Obnoxious and disliked" in his own words, his somewhat puritanical opinions and bluntness make him wholly unsuited for the position of Minister to France; he is later sent to the Netherlands, who like his style better but are too cautious to act.
Doctor Who: In "Marco Polo", Tegana spends most of the serial attempting to murder Marco and undermine Kublai Khan's court.
Horatio Hornblower: Mr Tapling joins the Navy in order to act as a diplomat, helping to establish contact with Muslims and buy food from them. He's demanding and rude and constantly complains about conditions on naval vessels, and his attitude towards said Muslims is not very understanding either. He improves after Horatio puts him to work with the steward as cooks. They are on a quarantined ship and everybody must lend a hand. Later he even owns that seeing people content with his work gives him a sense of accomplishment and satisfaction.
In Doonesbury, Duke served as ambassador to China in the mid-1970s, where he introduced himself by saying that he had come "in the hope of fulfilling a life-long ambition — dropping acid on the Great Wall." During his stay, he was protected from causing any serious diplomatic incidents by his translator Honey's Tactful Translation.
Possible in Video Game/Tropico if your foreign affairs minister you hire is too incompetent. He or she can trigger a random disaster resulting in decreased relations with a particular country, triggering a rebel attack, or cutting of foreign aid if you don't fire them.
In a traffic case of L.A. Noire, The Consul's Car, you have to investigate in a theft of an Argentinean Consulate vehicle (while not an embassy's, it still counts). As Argentina was a Fascist Dictatorship at the time, it is practically a given that her diplomats and consuls would have been Jerk Asses. The Consul General himself even checks in at the police station for questioning (one officer comments on him wearing gloves and refusing to take them off at any point). He is not only snobbish and strong-headed, but may or may not also be a pedophile.
The final case of Ace Attorney Investigations features two ambassadors. One is overly-enthusiastic, while the other is incredibly self-deprecating. The latter eventually turns out to be the Big Bad.
Ambassador Donnel Udina in Mass Effect is at least equal-opportunity... he is abusive and arrogant towards both the other Citadel Races AND his fellow humans. He'll constantly insult and belittle you, whether you play the Renegade or Paragon, and at the end, he honestly thinks that you're gonna recommend him for a high post (Humanity's representative on The Citadel Council, or Emperor of the New Terran Empire, depending on your choice towards the end) - thus making him both self-centered, arrogant, narrow-minded AND stupid. However, Udina's actions are all consistent with his goals and reactionary to the situation at hand. Renegade or Paragon, Shepard leaves death and mayhem in his/her wake and keeps going on about the Reapers. Udina plays the consummate politician, spinning each step of the way to make humanity look competent, independent, strong, cooperative, trustworthy, and sane.
Although in the third game, he turns out to be a traitor, selling the rest of the Council out to Cerberus.
A moreminor example is the Krogan ambassador from Nokmore clan. However, this is justified due to Values Dissonance, as in Krogan culture, the ambassador must represent the strength of his people.
The Volus ambassador acts this way towards humans, resenting them for being on the fast track to the top of Citadel politics, while his own people have been waiting for a seat on the Council for centuries. Of course, he forgets to mention that he doesn't actually represent a sovereign state but a protectorate and thus has no right to expect a seat.
Luke fon Fabre in Tales Of The Abyss once gets appointed as an ambassador, whereas he started abusing his 'given authority' like hell, hence, his Fan Nickname for him in that period is 'Ambassador Asshat'.
In Final Fantasy VIII, this is Sorceress Edea's intended role when she's appointed ambassador of Galbadia; the Galbadian government plans to hold "peace talks" and use the sorceress's power to intimidate other nations in order to Take Over the World. Of course, she ends up taking over Galbadia herself.
Playing a Dark Side consular in Star Wars: The Old Republic lets you do some atrocious things, ostensibly on behalf of the Republic and Rift Alliance.
In Gunnerkrigg Court, neither the Court nor Gillitie Wood is particularly diplomatic. The Court tends to treat the Forest denizens like irritations, and the Forest tries to gain dominance by being aggressive and abusive. It falls to the Mediums to be diplomatic for both sides.
In Errant Story, Lucian, the elves' newly appointed Tsuirakuan ambassador really gets off to a bad start being both aggressive, demanding and above all loud. But referring to the Councilman/Archmage's beloved half-elf granddaughter as an "IT"in his presence, really took the cake, as the resulting explosion can attest to.
Lucian's predecessor Rarune was complicit in a previous abduction and imprisonment of said granddaughter, who was also his biological daughter. Yes, he had knocked up a Councilman's daughter on a diplomatic mission. Needless to say, elves aren't very good at diplomacy with humans.
In The Inexplicable Adventures of Bob!, starfish alien Ahem is still hanging around on Butane as a "foreign dignitary'', despite the fact that he no longer has any legitimate business there. Voluptua has called him a freeloader, and he doesn't deny it.
The blue-skinned ambassador from Oglaf would fit the bill, being a hedonistic rapist. However, the ruler of the country is much much worse and as such, really likes the guy.
Tesa, from The Meek considers her host to be a savage and a war criminal. As such, she is not particularly respectful. Her companion, Lethy, is much calmer and polite. Unfortunately for the two of them, their visit coincides with their host's wife being murdered. Lethy escapes relatively unscathed, but Tesa has half her face burned off.
In Quentyn Quinn, Space Ranger the Empire of the Seven Systems averts, or perhaps inverts, this with the Space Rangers. Despite being the vanguard of interstellar exploration and thus the most likely to engage in First Encounter situations, Rangers are given little to no training in diplomacy—- on the ground that the natives EXPECT the alien to act "alien", and the most common response to alien contact has historically been paranoia and mistrust of smooth talkers. A rough-spoken loner with a gun on his hip, paradoxically, calms people down because that is what they tend to expect and how they expect they themselves would act in a similar situation. well-trained diplomatic envoys come much later, after the new race sees that the citizens of the ESS put their pants on one leg at a time, metaphorically speaking.
In the Canadian cartoon series Chilly Beach, the local US consul is grossly incompetent and belligerent towards the local population, attempting to run over people in her limousine and referring to a Mountie as "that guy in the bellhop costume."
In the animated adaptation of The King and I Kralahome is an evil sorcerer who wants to kill the king.
He's just a Grand Vizier. Some actual Asses In Ambassador show up from Britain though; the king and even the Kralahome try to be nice to them, but they're still contemptuous of Siam.
See how large the Star Trek entry is above? Well, there's one in Star Trek The Animated Series, too. "Commander Bem" (a pun on the acronym for "Bug-eyed-monster") starts off by spending weeks of his supposed ambassadorial tour of the Enterprise locked in his quarters, then suddenly insists (despite repeated gentle warnings against it) that he accompany them on their next away mission. And during the away mission, he steals their phasers and replaces them with duds, and harasses the local natives and gets himself caught at spear point. The planet itself needs to tell him to grow up before he starts acting tolerably. Is he trying to piss everyone off on purpose, or is his brain just not plugged into reality?
Which brain - the one in his head or the one in his butt? He is revealed to have several, so consistency of behavior may be a little to much to ask.
As for being "well versed in the customs and minutia of their culture," one way diplomats fail to adhere to this in real life is failing to realize how the government and legal system of their posting works, therefore making illegal and even impossible demands of their hosts. Any situation in which an embassy makes demands like "Punish those who belittle my country, or else!" will usually be an example of this trope. Sometimes this is due to ignorance. Other times it is done knowing that the other nation can't comply, but it looks good on their propaganda to say, "Hey, we asked them to stop it and they didn't. See? They don't care about us. In fact, they condone that behavior." Though to be fair, carrying rude messages from one's government is just a part of a diplomat's job sometimes. It doesn't mean that particular person is rude.
Diplomats from various authoritarian countries (China in particular) have pestered the Norwegian foreign ministry and warned them that there will be repercussions if the Nobel committee awards the Nobel peace prize to dissidents from their countries. Of course, the government has no say in who the committee chooses to give the award to, nor do they have any legal means of sanction against it.
The Chinese Embassy in Australia recently asked a local film festival to cancel the screening of a film by a Uighur film-maker and activist for Uighur rights. Needless to say, the festival refused to do any such thing, much publicity was raised, and many more people went to see the film than would have if there had been no such demand. Some even went just because of the Chinese demands, as a kind of small personal show of support for democratic rights and freedoms.
Another incident like this occurred in Denmark in the wake of the Muhammad caricature controversy. A group of ambassadors from predominantly Muslim countries requested a meeting with prime minister Anders Fogh Rasmussen, ostensibly to discuss perceived belittling of their religion and ask him to intervene against the paper that published the offensive drawing. Rasmussen flat out refused to see them, rightly pointing out that no Danish law had been broken and that his powers in no way allowed him to interfere like they wished and that therefore they had absolutely nothing to discuss.
William Dodd, ambassador to Nazi Germany from 1933 to 1937, attempted and failed to explain several times that the US Government has Freedom of Speech and Freedom of Assembly, and thus it can not shut down anti-Nazi rallies. The concept was entirely alien to the Nazi government.
Averted in the case of Antoine-François Andréossy, the French Ambassador to Britain during a brief truce in the Napoleonic Wars. Despite Napoleon taking offense of caricatures of him in the British press, Andréossy frequently advised him to ignore it. Not that that stopped Napoleon from pressuring the British into trying one of the journalists for libel. His secretary wrote that his dislike for British caritcature was the main reason the peace failed.
American ambassadorships are generally used by the President to pay off favors incurred during the campaign, and are not usually given to particularly qualified individuals. The station chief in the embassy is a career State Department official, and actually runs the embassy.
No driver of a diplomatic car has ever been taught the meaning of the no parking sign. At least they sometimes get karmic justice when whatever was the reason for the no parking zone falls on their car. Much fun will be had by all.
Historical examples (arranged in rough chronological order):
Apparently a missionary to China was once asked if Confucius had been saved (in the Christian sense). The missionary replied that if the great Greek and Roman philosophers had not been saved, what chance did Confucius have?
As noted above, John Adams was wholly unsuited to being Minister to France: he was puritanical where the French court was not, he was very blunt where the French were typically underhanded, and to top it, his French wasn't very good. The Dutch, on the other hand, did like him; you see, they were also puritanical, capitalist, and straightforward people, and he got considerably better results in Amsterdam than Paris.
The French Ambassador to the United States during the XYZ affair in 1798. He managed to start a war between the USA and France almost on his own.
Talleyrand and Metternich were both well known for being Insufferable Geniuses. Talleyrand was known not only for that but for being incredibly corrupt and treacherous enough to compete with Alcibiades in the treachery scale. Oddly enough their respective employers (France and Austria) seem to have known their faults but accepted them because each one was a Magnificent Bastard, which was often useful.
Joel Poinsett managed to be an ass before the USA even appointed official ambassadors. As a Special Envoy To Mexico, he became known as so meddling and quarrelsome, in Mexico they call a no-good politician a "Poinsettismo" to this day. At least he managed to get the Poisettia named after him.
Henry Lane Wilson made the American Government unhappy when they found out he was one of the guys responsible for Francisco Ignacio Madero's death and subsequent coup d'etat.
Joseph P. Kennedy, father of President Kennedy and American Ambassador to Great Britain in 1938-1940, was a strong supporter of appeasement (which, by itself was not indicative of this trope, as many people were prior to the war). However, when war finally broke out, his comments along the lines "Democracy is finished in England," and that Britain was going to lose the war were not taken well by the British (and were seen as particularly insensitive seeing as he moved himself to the countryside during the worst of the Blitz). He was also something of an Anglophobe, which didn't help endear him to his host nation. He was replaced by John Gilbert Winant whom the British loved.
Franz von Papen was an internationally recognized Ass In Ambassador. Before his assignment to Turkey in World War II he had gotten himself declared persona non grata in the USA, helped engineer the Anschluß in Austria, and even been credited with helping Hitler rise to power.
Joachim von Ribbentrop was a notorious ass. He entered Britain full of admiration for the British; he left seething with resentment because they let him know how much of a pompous asshole he was. Most Nazis didn't like him either and he was far too egotistical and fraudulent to be good at his job (the "von" part was a title he got by paying his aristocratic aunt to adopt him; hence the taunt that he "bought his title"). He managed to make the Molotov-Ribbentrop Pact though.
His portrayal by Turtledove (see above) is even worse. He's not shown as a competent ambassador at all. Molotov constantly sneers at him both for Germany's betrayal of the Pact and him being incompetent. During the negotiations with the Race in Cairo, von Ribbentrop refuses to back down on Germany's claim to Poland, despite Molotov also saying that the Eastern half belongs to the USSR, and despite the fact that the lizards are much stronger militarily than most of the world nations combined. Molotov is just about ready to scream out "You fool!" then barely remembers that he's supposed to be stone-faced.
The man was accommodating when he should have been harsh, meaning that other countries wrung excessive concessions from him, and harsh when he should have been accommodating, which meant that everyone thought him a Jerk Ass. Case in point: In order to try to get Turkey to join the Axis, he cancelled a Turkish order of 60 howitzers and refused to refund it. This had the result of making the Turkish Army despise him and oppose any relationship with Germany.
Ribbentrop's time as ambassador to the UK could be the subject of a sitcom. Here are some of his triumphs: Nearly knocking King George VI over by giving him a surprise Nazi salute, believing Britain to be run by an aristocratic clique maintaining a democratic facade, advising Hitler that the Wallis Simpson affair would lead to civil war, making appointments with all the fashionable tailors of London and then throwing them off, with the result that they then told all their (influential) clients how much of an ass he was, and, his crowning moment of moronic,telling Hitler than Britain and France didn't have the will to fight over Poland.
When the BBC filmed a documentary about him, every single interviewee expressed a passionate hatred for him. In all the memoirs of diplomats and politicians describing the lead up to war, there are only two positive references to Joachim von Ribbentrop. Neither refer to his skill as Ambassador or his personality. His aide said of him:
Reinhard Spitzy: When Ribbentrop strutted through the [Foreign Office] corridors like a peacock, his head thrown back, it was a miracle that he did not fall over. His deportment aroused great mirth among the British officials, who often grinned at me with a pitying look...
Herman Goering, despite being a Fat Bastard, got a brilliant crack at him:
Adolf Hitler: He knows many important people in England.
Herman Goering:Mein Fuehrer, that may be right, but the bad thing is, they know him.
Molotov. He was more like a school bully than a diplomat. How many diplomats have their names used as nicknames for "improvised hand grenade"?
The term "Molotov Cocktail" comes from his diplomatic machinations. When Russia started bombing Finland, he claimed to the rest of the world that Russia was dropping food aid, not bombs. So the Finns started calling Russian bombs "Molotov bread baskets." Then the Finns decided they needed something to drink to go with the food.
Being a former revolutionary terrorist does not necessarily make for savoir-faire. He was quite good at his job, all things considered.
Harry Turtledove's portrayal of him in Worldwar is a definite historical upgrade. He's shown to be a pretty decent negotiator, even though he staunchly sticks to Soviet ideology. He does, however, have to deal with Stalin almost on a daily basis, which is never a pleasant experience. A wrong word can get you sent to the gulag. He greatly despises von Ribbentrop, partly because the latter has fooled him into negotiating the Non-Aggression Pact, which Germany then violated. He also, apparently, feels himself perfectly fine in free fall when taken aboard the Race Conquest Fleet bannership in orbit. He's particularly known for never showing his emotions and hating flying.
Whilst Molotov was certainly an immoral human being, he was an extremely good negotiator. During his summit with Hitler and von Ribbentrop in 1941, Ribbentrop was to meet him in the morning and Hitler in the afternoon. Molotov whipped Ribbentrop so badly that the man had to flee and get the Fuehrer to help him. Molotov proceeded to take apart the Fuehrer too. All they could do was repeatedly claim that the British Empire was finished (despite a British air-raid forcing them to have their conference in an underground bunker) and offer feeble territorial concessions from it. His response was one of the cheekiest things anyone had ever said to Ribbentrop.
Nikita Khrushchev in his famous "shoe pounding" incident. In fact he planed that deliberately as a propaganda gambit; he even brought an extra shoe in so he wouldn't have to take one off. In that case he was a head of state but he was in a diplomatic meeting and anyway that story is just too memorable to forget.
Charles De Gaulle's little speech ("Vive le Québec Libre!") at Montreal, during Expo 67, was not a very clever move on his part. Quebec separatists view him as a hero; Quebec federalists, Ottawa, and the rest of the country were deeply insulted. To top it off, he took umbrage when then Justice Minister Pierre Trudeaugave him a taste of his medicine publicly musing how the French President would like it if the Canadian Prime Minister went to France and said, "Brittany to the Bretons."
More recently, France's former president Jacques Chirac, while not an actual ambassador, was a real life instance of the ambassador too eager to learn of another country's history. Specifically, he was very knowledgeable about Japan's history and customs, to the point of knowing more about Japan than Japanese officials. Things started to get awkward when he tried to ask them precise questions about minor points of Japan's history, and they were unable to reply.
One Saudi prince tried to sexually harass a woman from a rich family and ended up sent home for it. His father Abdul Aziz Ibn Saud beat him with his own hands for embarrassing him. Apparently the prince never dreamed that her family would react the way an Arab family might react (except some Arab families prefer daggers to persona non grata on such occasions; but same principle).
Another Saudi Prince quite recently thought he could get away with beating his servant to death under questionable motives. Whilst he dodged prosecution in the UK for his crime, he fled home only to face down homosexuality charges for his supposed indiscretion, which carries the death penalty in his country.
Paul Celucci, US ambassador to Canada from 2001-2005, started off well when he was about the only US government official to remember Canada's role in the events following 9/11...and then things went downhill from there. He was noted for his speech chastising Canada for not supporting the US invasion of Iraq, while claiming the US would never hesitate to assist Canada in the event of a conflict (people immediately pointed out that in the United States, World War 2 officially began in 1941, two years after Canada had entered the war), and his general attitude which was summed up as "ambassador to a friendly nation trying to act like its governor." When his term ended, Rick Mercer joked that the speech covering his farewell would be called "Don't Let the Door Hit You on the Ass."
The Romanian diplomat who caused a car accident in Singapore, refuses to apologize for it and will not stand trial for it either. His chances of being tried are low, considering the two countries have no extradition treaty.
The foreign relationships of Venezuela had suffered for having diplomatic posts given more because of loyalty to the regime than actual capacity for the job, with results often quite detrimental for the country image. Gustavo Coronel compiled a selection of the most notorious gaffes, including the murder of the Ambassador in Kenya Olga Fonseca, suspected to be payback for her hasty dealings with the people who accused her immediate predecessor of sexual harassment.