"Joachim is useful — he knows many important people in England."
"Yes, mein Führer, but unfortunately they know him."
— Adolf Hitler and Hermann Goering, on Joachim von Ribbentrop.
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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All of the Nations in Axis Powers Hetalia are this when interacting with each other, often culturally insensitive, argumentative, and rude. However, some are this more often than others - particularly America and France.
Justified in Log Horizon with the merchant Marval, who is actually an agent tasked with provoking the country he's visiting into causing an international incident, disrupting the vitally important diplomatic event it's holding and discrediting its leadership. He does this by being the most gigantic asshole possible.
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.
Later we meet Hansel (who was previously exiled for murdering his sister, Gretel) as the ambassador from The Empire. The mere choice of him as ambassador was a deliberate insult, but he then proceeds to be such a spectacularly JerkassSmug Snake that he would certainly have alienated Fabletown even without his previous history with them. The fact that they soon discover he's been sent as an infiltrator actually makes the Fables' lives easier, as it frees them of any moral obligation to not screw with him any way they can, and they only need to rely on the letter of diplomatic immunity rather than the principles of negotiation and compromise.
In the Ghost Trick fanfiction Twisted Fates, the Little Ambassador's generally a nice guy, but he also keeps his office full of spiders, snakes, and a live bear. Anything that's not poisonous (including the bear) is left to wander freely. The animals do seem tame enough that they don't hurt guests, but he tends to forget that they make visitors uncomfortable.
In the Holocaust drama Conspiracy, Martin Luther is the Undersecretary of the Foreign Ministry, representing Joachim von Ribbentrop at the conference. He's almost as obnoxious as the disgusting Klopfer, participates in a bunch of lurid jokes about forced sterilization and proudly declares that he would be willing to sign up for Major Lange's death squad if they needed someone to shoot women and children.
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 — or rather, the most fundamentalist dwarves do. The country he is sent to apparently tends to regard it as a terrible and important responsibility).
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.
In the novel Sarek, Klingon Ambassador Kamarag (identified as being the same ambassador as seen in Star Trek IV and Star Trek VI, who was never canonically named) attempts to start a war between the Federation and the Klingon Empire, with the intention of returning as a conquering hero and usurping the current Chancellor. And it turns out that a another ambassador, Taryn of Freelan, had his agents telepathically manipulate Kamarag into doing this, because the "Freelans" don't actually exist as a people; they're really just disguised Romulans.
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.
Which is probably because they did try-Descroix at least is a secret agent for the Mesans, and they really badly want Manticore and Haven to destroy each other.
From Crown of Slaves is the ambassador responsible for bungling the Erewhon alliance, one Countess Deborah Fraser. Her cousin, Captain Michael Oversteegen, is less than impressed with her (lack of) diplomatic finesse:
Oversteegen: I will leave out of all this the petty consideration that we're talkin' about the life of a teenage girl. I realize that's a matter beneath your contempt. I will just take the opportunity t' tell you, since I don't believe I've ever done it before at one of our family gatherin's — not precisely, I mean — just how brainless you are, Deborah. Truly brainless. Not simply stupid. Bar-ain-less. As in: brains of a carrot.
Fraser: You can't—!
Oversteegen: You imbecile! First of all, the entire inhabited galaxy will most certainly hold us responsible for our own actions—or inaction—in this episode. But it really doesn't matter, Deborah. It certainly won't matter t' you, that's for sure. Because if Anton Zilwicki decides you were responsible for his daughter's death, I can assure you that the man won't be in the least impressed by your official lack of responsibility. He's a rather notorious fellow, don't you know? Not given, so far as I can see, t' much in the way of respect for his betters. This conversation is ended, since it was obviously pointless t' begin with. I will remind you, Madam Ambassador, that as the senior naval officer in the system, I am obliged to 'coordinate' with you but am in no way under your authority. So, Deborah, consider us havin' 'coordinated' — you are a cretin and I told you so — and I will attend t' the Queen's business.
Sealer Greenlaw in Diplomatic Immunity is a mild example. While she claims long diplomatic experience she has clearly never dealt with an interstellar crisis before, makes a hash out of what is really a harbor brawl that got out of hand, and waste time on petty self-righteousness. Still she does have enough to be angry about. A worse example from the same book is Admiral Vorpatril, who sends a security patrol onto sovereign foreign territory to apprehend an AWOL, and messes things up when said patrol beats up a dancer and renders her unable to perform in the process of said apprehension. Which in turn forces The Emperor to send an Imperial Auditor (Miles) when a little tact might have gone a long way toward solving a problem that was reasonably similar to normal jurisdictional difficulties with local police that an admiral should be used to.
For the Emperor, the first Ciaphas Cain novel, has an aide to the Tau ambassador Cain suspects of having a death wish. After the ambassador is murdered, he starts accusing every human in sight of doing it and attempts to kill the governor due to sheer paranoia. Later, when the Tau are being smuggled back to their embassy through a hostile part of town, he jumps up at a mention of a Tau conspiracy, forcing Cain to order the PDF roadblocking them shot. Cain notes no small amount of irony when, half a book later, it turns out the governor he tried to shoot was the assassin.
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 Jerkass 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. Heck, he was even getting effective in the gap between doing his job and usurping Scotty and Kirk's job, which was spent wielding a disruptor and being ready to use it. Definitely a cut above most TOS Federation officials, if only because that's not much of a contest.
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-Betazoids (despite having married one), 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 actual negotiations, however, she is shown to be ludicrously efficient and effective, making her a cross between this and Bunny-Ears Lawyer.
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.
In the computer game Star Trek Trivia Challenge, one of the questions is about what Picard accuses Spock of in "Unification, Part II" with one of the possible answers being "Putting the 'ass' in 'ambassador.'" (The correct answer, by the way, is "Cowboy diplomacy.")
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 finally snaps to Sisko: "NOTHING MAKES THEM HAPPY! They are dedicated to being unhappy, and spreading that—UN-happiness wherever they go! They are—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 Tellarites literally have this as their Hat. The above-mentioned "Journey to Babel" shows that this has not changed at all a century later, as that episode's Tellarite ambassador is the biggest ass of them all.
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 Head-in-the-Sand Management.
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. On the other hand, he does manage to get the UN Security Council to re-schedule its debate on the invasion of Not!Iraq, at Malcolm's behest, something he assured Malcolm was totally impossible. Twice.
Cory in the House: Raum Paroom, the Bahavian ambassador to the United States, and father of the title character's best friend/love interest, smugly asserts the superiority of his own culture while disparaging American 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.
One of Barry Humphries' comedy personas, the rude and loud-mouthed 'cultural attaché' Sir Les Patterson, is this to a tee.
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.
Warhammer 40,000: One of the Tau codices has a fluff piece concerning a diplomatic visit to a Tau world. While the diplomat himself is an Ordo Xenos inquisitor and quite polite, his bodyguard is a Space Marine Captain of the Imperial Fists, and considerably blunter (that the tour just happened to take them past an assault course looking remarkably like a gutted and plasma-blasted Imperial city didn't help).
In the musical Leave It to Me!, Alonzo P. Goodhue is unwillingly appointed ambassador to Russia, invokes this trope in order to get himself recalled.
Possible in 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 Jerkasses. 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) - thus making him both self-centered, arrogant, narrow-minded and stupid. However, Udina's actions are all consistent with his goals being to further human interests. Also, Renegade or Paragon, Shepard leaves death and mayhem in their 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 sells out the rest of the Council to Cerberus. Whether this is simple avarice and a selfish power grab, or desperation brought on by Earth being little more than rubble, is hard to figure out since you kill him before he can say anything.
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.
Elenwen of the Thalmor is this in The Elder Scrolls V: Skyrim, as she's openly hostile to her Imperial allies while ruthlessly sending off her own subjects to be tortured. She almost sabotages a temporary peace conference that you need to complete in order to trap a dragon. And she helped start the civil war by using psychology to guilt trip Ulfric into believing that he had to "own up" to his mistakes when in fact he didn't cause that intel failure that killed a legion of Nords.
Ancano is the mage equivalent of ass. It's obvious from the get go that his job is ambassador to Winterhold is to harass everyone (even the altmer living there) and look for any opportunities for the Thalmor. Suddenly, a giant orb containing an intricate flux of pure magicka so strong that the first settlers caused genocide to prevent it from seeing the light of day. What does Arcano do? Call for reinforcements, kill everyone in the College, and use the orb to conquer Skyrim, and possibly Nirn? Nope! Worse! He programs it to self-destruct and does his best to make sure that no one intervenes, threatening to destroy all of Nirn in the process. You'd think that the Thalmor would ostracize him for almost killing everyone, but we're not sure. Given certain details about Thalmor philosophy, Ancano may very well have been doing what they wanted the whole time. They certainly don't appreciate the Dragonborn stopping him, as they send agents to kill them after Ancano's death.
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 he's posted to 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."
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.
Shocking enough Wonder Woman of all people is this in Justice League: War. She bails on meeting the president because she didn't want to wait, cares little to nothing about the customs of the Nation she is in, and constantly thrusts her sword at people which clearly terrifies them. It has gotten so bad that at the beginning of the movie there is a protest group wanting her gone.