There are already enough jerkasses in the world, even without tossing in things like Poor Communication Kills. On the other hand, you get the genuinely nice and well-meaning people who honestly want to compliment someone else.
It fails horribly, of course.
There may be a few reasons for this: Suppose Julie wants to compliment Alice, but goes wrong because...
Chrono: Nanoha's combat ability is considerable. Your irresponsible reliance on your magic power complements your basic true character. Nanoha: Er... Chrono: You're extremely solid and quick to recover too. Nanoha: Er... Are you praising me or are you insulting me? Fate: Oh, he's praising you, really.
Akari, a character in the Ranma 1/2 manga, loves pigs and complimented Ryoga repeatedly by comparing him to a pig. He did not see this as a compliment, in part because he turns into a pig.
Akane did this herself to Ryoga once. He was very depressed and using that depression for a special attack, and Akane tried to cheer him up by saying "You're a good friend!" Cue Ryoga, who has unrequited love for Akane, getting even more extremely depressed than he was already! (note the Real Life section below)
Nodoka has insulted Ranma before by complimenting him on his cute, girlish looks or his talent at feminine tasks, because she has no idea that "Ranko" is actually her son. While Ranma loves being better than everyone else, he's not too thrilled that it's coming from his mother, the one person whom he needs to consider him manly.
Nodoka: You'll make a good wife to some lucky man, Ranko!
Ruby: Look at Ilya-san! Skip logic or the process and only imagine the result! Like that, optimistic thoughts are better than practical ones for being a Magical Girl! Ilya: Somehow, since a little while ago, you've been saying cruel things!? Ruby: No no, I was praising you. Having an empty head means you can stuff it with more dreams. Ilya: Don't just selfishly make people into idiot characters!
Naruto, when attempting to encourage Sakura, calls her a "master of brute force." Of course, being Naruto, he meant well, but that didn't stop Sakura from getting mad. And then hitting him.
On that note, there's also when, during the "Invasion of Konoha Arc", Kakashi's ninken (summoned tracking ninja dog who can talk), who is leading Naruto and Sakura on the search for Sasuke, stops in his tracks. The reason? To comment to Sakura that he's just realised - from the smell - that she uses the same brand of shampoo in her hair as he uses for his fur. Cue Colour Failure and Narutoof all people calling him out on this random comment.
Dramatic version in Gundam SEED Destiny: After destroying the Freedom Gundam, Shinn tells Athrun "I got revenge, for me and for you," and gets punched in the face, prompting a "What the hell is wrong with you?!" Shinn was referring to a battle where the Freedom shredded Athrun's Gundam and badly injured him, but he has no idea that the Freedom's pilot is Athrun's Childhood Friend, whom he apparently just killed.
Also Played for Drama in Kodomo No Jikan, Aoki-sensei is pushed to transfer to a joint primary-middle school. He thinks this shows that the school board didn't trust him, despite everything he had done for his students. It turns out that they were more than satisfied with the job he had done; they merely wanted him to teach somewhere that his skills would be put to better use.
In Yu-Gi-Oh! GX, Judai Yuki is absolutely amazed by Edo Phoenix's Destiny Hero monsters and expresses how cool they are. Edo, who has absolute disgust and contempt for Judai at this point, is annoyed.
A Running Gag in Empowered. It seems Thugboy finds Emp's backside one of her most alluring features, while Ms. Powers herself often finds it disgustingly oversized (along with the rest of her). You can see where this is going.
One of the only times this compliment didn't backfire was when Ocelotina remarked that Emp's butt "quivers fetchingly" when spanked. When Thugboy confirms this, she is delighted.
In one issue of The Flash, Wally goes to Captain Cold's parole party, mingles with the Rogues, and ends up keeping an errant boomerang from hitting Golden Glider (who went into villainy after the death of her lover, the also-villainous Top).
Golden Glider: Thanks for saving me. You're not at all like Barry Allen. You're as brave and honest as the Top. Wally: I... but the Top was... Gentleman Ghost: I'd take that as a compliment, old thing, and let it go at that.
In another issue, he rescues the then-reformed Dr. Alchemy, who enthuses "I don't know why everybody says you're such a jerk!"
Hivefled: Vriska learns why one should not tell someone who was horribly tortured by his own parents that he should look on the bright side because his new scars are "fucking hardcore" when he responds by giving her some new ones since she likes them so much.
The captain of the Enterprise-B in Star Trek: Generations, to Captain Kirk: "I read about your missions when I was in grade school."
And in the 2009 movie Spock is complimented by his elders on overcoming the "disadvantage" of being a Half-Human Hybrid. Spock's response, while unflinchingly calm and polite, is very clear on where they can stick their praises. It is a credit to Quinto's performance in this scene that his "Live Long and Prosper" comes off clearly as "fuck off and die in a hole" without any obvious expression of emotion.
In Unseen Academicals, Mr. Nutt, whose social skills are somewhat lacking, tries to flatter the plump and plain Glenda by describing her as "fecund". Glenda is mortified, but dips down to "embarrassed" after she rushes off to look up the word, and manages to gently explain to Nutt where he went wrong.
Another Discworld example is in Jingo, when Vimes finds out that among the D'regs, being trustworthy is apparently an insult.
Ahmed: I left him (Prince Khufurah) with a woman I trust. Vimes: Your mother? Ahmed: Heavens, no! My mother is a D'reg! She would be terribly offended if I trusted her! She would say she had not raised me right!
Of course it's an insult. "D'reg" isn't the D'reg name for D'regs; it's a word from a different Klatchian dialect that they gleefully adopted, meaning "enemy". The D'reg word for "enemy" also translates as "target". They love to fight. They're an entire, richly-textured culture of cartoonish cliches.
From Harry Potter and the Half-Blood Prince, Ron compliments Luna on her commentary regarding a Quidditch match. The last reason for this kicks in here as Luna thinks Ron's mocking her because everyone else tells her she did a lousy job. (Considering her performance, it's easy to understand.)
Live Action TV
Farscape had Aeryn compliment Zhaan on being "a true warrior" after she almost singlehandedly defeated the episode's Big Bad when she and D'argo failed. Zhaan just looks shocked and quietly leaves. D'argo explains to Aeryn that Zhaan is a priestess and a fervent Actual Pacifist, who had seriously bent her ethics to beat the baddie. Essentially, "You could not have cut her more deeply."
The Muppet Show, where newcomer Annabel Sue Pig tells Miss Piggy of her lifelong admiration of her.
Frasier and Niles read a new manuscript by a reclusive novelist. They lavish compliments on him, including how brilliant it was to mirror Dante's nine levels of Hell in the nine rooms of a bordello. The author hadn't intended this, realizes he ripped off the entire structure from Dante, and throws the manuscript into the fireplace.
Spock: My congratulations, Captain. A dazzling display of logic. Kirk: You didn't think I had it in me, did you? Spock: No, sir.
Most of the crew have at one time or another told Spock that he has acted very human. While this is often meant as a sardonic jab or even an overt insult, it is occasionally meant to be a sincere compliment. Regardless of the intent, though, it always offends him.
Similarly to the Farscape example, the Doctor Who episode "The Doctor's Daughter" has Jenny complimenting the Doctor on his skill as a soldier.
Not to mention the episode "Dalek", in which the (supposedly) last surviving pepperpot compliments the Doctor on his ruthlessness, claiming that he would make a good Dalek...
A common problem with Simon Tam from Firefly in regards to Kaylee.
Simon: Plus, every other girl I know is either married, professional, or closely related to me, so you are more or less literally the only girl in the world. Kaylee: That's a hell of a thing to say. Simon: I was joking... Kaylee: No, no, I get it. Back on Osiris you probably had nurses and debutantes crawling all over you. But down here at the bottom of the barrel, there's just me.
Star Trek: Voyager. The Emergency Medical Hologram has a tendency to do this, even when he's not trying to be his usual Dr. Jerk self.
Kes:Neelix and Tom Paris had a physical fight over me. EMH: How delightful. Kes: Delightful? EMH: You should consider it a high compliment. Throughout history, men have fought over the love of a woman. Why, I can quote you autopsy reports from duels as far back as 1538. Kes: That's not funny. EMH: It's not meant to be. You've always been interested in autopsies.
Spaced has Twist, who constantly makes backhanded insults in the guise of compliments towards her friend Daisy. For example when Daisy appears on the scene of her birthday party at a restaurant with a brand new dress and make-up in an attempt to impress, Twist comments that she looks nice and follows that with "I wish I could dress down like that". This is particularly grating in that everyone else at the table hasn't even noticed the way Daisy looks and the atmosphere is already extremely tense for a multitude of reasons.
In an episode of Murder, She Wrote, Jessica is doing a book-signing at a police station and one of the cops comments "My grandmother will be thrilled. She's been reading your books since she was a girl." The fact this can't actually be true (Jess isn't that old, and she only started writing after she retired) is lampshaded by her Friend on the Force, who drily comments "I remember my great-great-grandfather telling me he read your books by candlelight."
In Dollhouse: When Topher is talking to Bennett, he says that "I had a crush on you even when I thought you were a dude." Bennett seems mildly creeped out by it, but appreciates it after Topher adds: "This is better."
In their first meeting there's also Bennett describing Topher as "very pale skin. Like a pig." and having to clarify that she likes pigs. They're an awkward couple.
In Full House, after Rebecca gives birth to twins Nicky and Alex. Joey goes into Cuteness Proximity mode, saying that they look like miniature Elmer Fudds. To this, Becky screams "MY BABIES LOOK LIKE ELMER FUDD!" and breaks into tears.
Pierce compares his ex-step-daughter's appearance to those of the call girls he frequents. It goes over about as well as you'd expect.
Britta's comment about the attractiveness of Troy's grandmother ends in her being spanked.
In the first episode, when Pierce tells Jeff "You remind me of myself at your age", Jeff's response is "I deserve that."
Screech from Saved by the Bell does this twice. The first time he makes this mistake, he tries to compliment his prospective girlfriend's mother with a celebrity... and he compares her with, of all people, Arnold Schwarzenegger. The other mistake involves an episode of The New Class series where Screech attempts to be complimentary to Mr. Belding when introducing him to Kareem Abdul-Jabbar:
Screech: This is Mr. Belding, the man who made me what I am today! Kareem: (Turning to Mr. Belding) Mr. Belding, we need to talk.
In Scrubs JD means to compliment Julie when he says "you smell like my mom". Naturally this has the opposite effect. Thankfully he saves himself...
JD: I didn't mean you smell like my mom, I meant you smell like mamum. It's a rare fragrant herb. Julie: (hugging him) I feel so silly. JD's Narration: (sniffing her) Ah, Mommy.
In True Blood Arlene attempts to comfort Sookie by saying "you really are smarter than people give you credit for".
Sheldon Cooper, the Insufferable Genius on The Big Bang Theory, sees even fields such as experimental physics and engineering to be beneath him, and takes offense when his sister tells him that she's always bragging to her friends about "my brother, the rocket scientist".
Sheldon: You tell people I'm a rocket scientist??? ...Why don't you just tell people I'm a toll-taker at the Golden Gate Bridge? Rocket scientist. How humiliating.
In an episode of Blossom, one character recently introduced to another says "I don't care what they say, you keep wearing that shirt."
Castiel (to Dean): You are not the burnt and broken shell of a man that I believed you to be.
Greg's Double Entendre introductions on Red Eye With Greg Gutfeld are meant to be complimentary(except to Bill, but often end up being this trope. Introductions such as "She's so hot, Smokey the Bear flings feces at her" can be less than flattering.
"She's so hot, when dogs go into heat, it's called 'going into Jill Dobson'" prompted a faux walk-off from the person in question.
At one point in Game of Thrones, Sansa promises Cersei that she won't be any trouble: "I'll be a good queen just like you, I won't hatch anything!" Cersei's reaction is priceless.
"Weird Al" Yankovic's "That's Your Horoscope for Today": "You are the true lord of the dance, no matter what those idiots at works say."
In the Redeye comic strip, the incompetent brave tried to butter up his chief with the line, "You don't sweat much for a fat guy." The brave intended it as a compliment. This is a gender-reversal of a real life line Alex Karras originally said to a girl he was dancing with, with the same intention.
A Dilbert comic listed one of "The 7 Habits of Highly Defective People" as "use compliments to show your prejudices". The corresponding picture showed the Pointy-Haired Boss telling Alice "Ooh, nice crisp photocopy, Alice. I don't think a man could have done it better!"
A Garfield strip shows Jon telling Vet Liz that because animal medicine is a difficult field, she must "have a great mind for a woman." She, offended, responds, "I have a great mind for a MAN." He attempts to flirt by telling her she has "a great body for a man too."
Overboard - Nate urges Charley to say something nice to the Captain, seeing as it's his birthday - on such short notice the best Charley can come up with is "Wow - you barely look insane today!"
One strip of Out of the Gene Pool has the baseball player Puff Maghee punching out a sports reporter. Another reporter on the scene points out that the term Cinderella Story is a compliment.
Hall-of-Fame first baseman Lou Gehrig had an off year in 1938, but manager Joe Mc Carthy kept him in the lineup throughout the season. He was much worse at the beginning of 1939, but everyone still thought he'd play through it. The end came in a game when he fielded a soft grounder and flipped the ball to the pitcher covering first base to end the inning. On the way back to the dugout, his teammates mobbed Gehrig, patting him on the back and congratulating him - for making a routine play. Gehrig realized how bad his performance must have been for his team to be complimenting him on something so basic. In his words, "They meant it to be kind, but it hurt worse than any bawling out." Gehrig retired shortly thereafter. He was later found to be suffering from amyotrophic lateral sclerosis, a disease which today bears his name. Two years later, he was dead.
The bridesmaid Zorah has a line like this in Ruddigore: "Dame Hannah, you're a nice old person..." Play it right and it always gets a laugh from the audience.
Set up and then subverted in Mary, Mary. Bob, at a loss at how to win back Mary, says she doesn't know he believes she's pretty. He never got to tell her that she was as beautiful as "a lovely piece of white porcelain," because he knew what she would say: "White porcelain? You mean like the kitchen sink?" Indeed, in their final reconciliation scene, he gives her that compliment, and her retort is as predicted, except that she catches herself in mid-sentence and goes sweet.
Cyrano de Bergerac: Cyrano tricks a poor Bore to invoke this trope (so he can literally kick the Bore's ass) at Act I Scene IV: When asked if his nose is large, the Bore desperately says it’s minute:
Cyrano: Why then that air Disparaging? -— perchance you think it large? The Bore(stammering): No, small, quite small—minute! Cyrano: Minute! What now? Accuse me of a thing ridiculous! Small—my nose?
Flattering another player in Anno 1404 for diplomatic purposes may result in this, especially when you try too hard or too often. For instance, Willem van der Mark, a depressed Dutch intellectual, will express his regret over a book he wrote after you lauded him for it.
A lot of a male player's attempts to compliment Nathyrra in Neverwinter Nights Hordes of the Underdark are...ill-received (at best).
Though by chapter three she seems to have decided that the player character is joking.
Played absolutely for drama in the backstory of Shiki from The World Ends with You. Shiki and her best friend Eri work together to design and make clothes, with Eri doing the designs and Shiki taking the construction. Shiki always felt inferior and wanted to be a designer too, and the eventual argument about this culminated in Eri telling her she "just wasn't suited to being a designer." She meant that Shiki was such a good, detail-oriented seamstress that turning her attention to designing would be a waste of her skill, but Shiki took it... poorly. And ran away crying. And died in an accident before Eri could explain.
In Freefall Sam's idea of complimenting Florence is "You look good ... for a dog in a dress."
Amy from Futurama does this to Leela a lot. To whit:
Amy: Those are great shoes! Leela: Thank you. Amy: Do they come in women's sizes? (Leela smashes Amy with the Planet Express Ship stairway ramp)
Chip 'n Dale Rescue Rangers had a poodle actress (dog food commercials, Lassie takeoffs and the like) as a recurring guest star. Every time someone says how much they admire her, they tell her they've been fans for years and years. And years. And years...
Come to think of it, how old is Carol Channing?
In the Animaniacs Goodfeathers sketches, Pesto ALWAYS takes Squit's compliments as insults. Granted it's obvious and it was a spoof of Good Fellas but still...
The compliments weren't what was messed up, it was Pesto that was broken.
Zuko: Uh... you have... quite an appetite for a girl. Jin: ...Thanks?
In another episode, Aang and Katara are stuck in a cave and... this happens.
Aang: Well, if there was a choice between kissing you and dying... Katara: (makes an offended grunt} Aang: What, I'm saying I'd rather kiss you than die, that's a compliment!
Yeah, Aang is guilty of these. Take this one he gives Zuko, whose initial smile fades as he processes the compliment.
Aang: You know, Zuko I don't care what everyone else says about you, you're pretty smart!
During one of the video sequels to Disney's Tarzan, Tarzan mentions how much more used to getting around the jungle Jane is. "You act more like an ape every day!" "Well, I never -" (sees his confused expression) "...heard such a sweet sentiment."
On Jimmy Two-Shoes, Lucius gets Jez a giant, solid gold statue of herself for her birthday. her reaction? "So you're saying I'm big? Is that it?"
In an episode of Snooper and Blabber the duo are disguised as servants protecting the valuable diamond of a matron whose 65th birthday is being celebrated. Snooper gets the cake thrown in his face after quipping to her "You'll never see 60 again!"
Due to her snooty nature, Lacienega from The Proud Family has a unique gift for being insulting even when she makes an attempt at a compliment.
Mary Whitehouse, patron saint of Moral Guardians in the UK, once praised The Goodies as the sort of decent, wholesome television she'd like to see more of. The boys were horrified, and rapidly produced an episode called "Sex and Violence", featuring Beryl Reid as "Mrs Desiree Carthorse".
Under Tony Blair, the UK government drew up a list of celebrities to be encouraged as good role models for children. When actress Emma Thompson found out she was on the list she told the press her immediate reaction was "an overwhelming desire to go out and score a load of cocaine in rebellion."
Then again, nobody measures anything in Edisons...
Journalist Johann Hari decided it was definitely time to change his diet and get in shape when the staff of his local Kentucky Fried Chicken gave him a Christmas card and a round of applause for being their best customer.
Todd: The more I look at this (amazing) fanart of me, the more I wonder what the artist thinks of me. My world is bleak, muted, gray. I am bored. I turn on the radio. My world is suddenly filled with bright, vibrant colors. I am shocked and quickly begin criticizing the colors, harshly. Then, I run out of energy and return to my boredom and my bleak, dull room. What does this mean about me?
"Is any man wiser than Socrates? / No." The rest is, very literally, history.